Ultimately, Vegas will be what you make of it. If you want a sleepless trip filled with debauchery and nights you won’t forget, you can have that. If you want pure relaxation with the most memorable meals, you can also have that. I’ve been to bachelorette parties, birthdays, work events, and romantic long weekends. I’ve even been there for a wedding! My last trip, and what this 3-day itinerary is based on, was a balance of activity and relaxation without being overly scheduled.

Before we jump in, let’s review some of the things Veags is known for since they will be sprinkled throughout. If you go somewhere and they are known for something, you should have that thing. I learned this lesson the hard way when I went to a gelateria in Venice and had the worst sandwich of my life. That’s a story for a different day.

• The Strip – The Las Vegas Strip is like small-town USA main street on steroids! Las Vegas Boulevard, the official name, is four miles long. The majority of major hotels, shopping, and restaurants are located directly on it.
• Gambling – There are over 100 casinos in Las Vegas and they never close! While I’m not a big gambler, I like to see what a few bucks can do. For me, it’s strictly entertainment.
• Dining – What’s great about Las Vegas is that the best restaurants from the best cities in the country inevitably open locations there. So you can be in one location and try restaurants from all over! Many times a celebrity chef is also tied to the restaurants, which is always fun!

If you buy something through my links, I may earn a small commission at no additional cost to you. I appreciate your support! See disclosure for details.

Where is Las Vegas?

Las Vegas is in the Southwestern portion of the United States and it is in the Mojave Desert. Vegas is 270 miles southeast of LA and its elevation is around 2,000 feet. It is located in Pacific Standard Time Zone.

When to Visit Las Vegas?

As noted above, Vegas is in the literal desert. The temperature may be over 100 degrees in the summer and 20 degrees in the winter. The best time is Spring and Fall, when there is a slight briskness in the morning and late at night, but sunshine and warmth during the day.

These seasons are especially great if you are coming from an area with four distinct seasons since it may not be the ideal temperature there. When I went in April the weather was gorgeous, high 70s, and it was still cold back in Chicago.

Can’t Miss Things To Do (aka Very Obsessed!)

Top three things from this Itinerary:

• Fountains of Bellagio Water Show
• Dinner at Superfrico
• Slip a $20 in a Slot Machine

Itinerary Overview

Where to Stay in Las Vegas

During the course of the 20+ years I’ve been visiting Vegas, I’ve stayed in my fair share of hotels and they have run the gamut of every price range. These days my favorite place to stay is Aria. Below I’ve noted a few of my Aria highlights!

Aria is a 5-star hotel that is located on the south end of The Strip. Not only is it a must that the hotel is on The Strip for ease of walking, but the south end is my favorite area with its close proximity to Cosmopolitan and Bellagio. Aria is part of MGM, so you’re eligible to earn rewards, as well as Marriott Bonvoy, so you can earn points. Not only do they have excellent dining options, but they are also home to the largest Forbes Five-Star Spa in the world. It’s the Goldilocks of vibes, not too young (no day parties) and not too old (plenty of young-ish people).

Day One | South End of The Strip

Day

This is either your travel day or you traveled yesterday. Either way something not too fussy for breakfast is what is on the agenda. Just because it’s not fussy though doesn’t mean it’s not amazing! Eggslut is an LA-based breakfast sandwich fast-casual spot that has fresh ingredients and is made to order. It’s on the Mezzanine level of Cosmopolitan, about a 6-minute walk from Aria, and the line is long. It goes fast though so don’t let that deter you, maybe just plan on going 30 minutes before you are ravenous, haha.

After you’ve filled your belly it’s time to walk the Las Vegas Strip. I love to wander the strip with no exact destination in mind, and let it speak to me. Along the strip, you will find most hotels, so you can always pop in and grab a cocktail, snack, or gamble for a bit. There is also a TON of shopping to be had, I can’t even count the amount of Louis Vuitton or Hermès stores I’ve seen. These shops will be connected to the casinos or in Fashion Show Mall, on the north end of the strip. Lastly, there are just random places, a particular favorite is the Coke Store where you can get a flight of sodas from all over the world.

Night

You will have walked many steps by evening so you may want to go back to the hotel and get ready for dinner. Superfrico is located inside the Cosmopolitan and is described as an ‘American Italian Psychedelic’ restaurant. Without giving anything away, the cocktails are fun, the food is great, and the entertainment is amazing! I suggest making a reservation for 7:00 or later. When dinner is over, head next door for the 9:00 pm show at OPM. It is from the same group as Superfrico and will not disappoint! If you want a little sweet treat before you walk back to Aria, stop by Milk Bar on the Mezzanine level at the Cosmopolitan and try the cereal milk ice cream or grab a cookie for the road.

Day Two | North End of The Strip

Day

After last night’s festivities, you may want to sleep in and that’s great because we don’t have anything on the agenda until brunch! Since Mon Ami Gabi has an outdoor patio and is situated directly across the street from the Bellagio fountain, make your brunch reservations at noon or later. The Bellagio Water Show is not to be missed and starts at noon on Saturdays, Sundays, and holidays, meaning you’ll have prime viewing!

Next, we’ll wander north to see that side of the strip. Feel free to stop in any casinos or stores you’d like. One notable casino to check out is The Venetian where you can ride a gondola on canals inside and outside of the casino, just like you’re in Venice! Like many casinos, they also have a ton of stores to shop to your heart’s content.

While you’re in the area, check out The High Roller, the Ferris Wheel at The Linq. You’ll get a bird’s eye view of Vegas in a comfortable, and oversized cabin. They often offer special events as well. A few years ago I did a yoga class, in the Ferris Wheel, and it was amazing!

Night

As a Vanderpump Rules fan (and most things Bravo) I would be remiss if I did not include one of Lisa Vanderpumps Restaurants in this Las Vegas itinerary. Although I understand it’s not for all. Of the two spots, I suggest Vanderpump à Paris on the ground floor of Paris. The decor is like a sophisticated Moulin Rouge and the drink presentation is outstanding!

If LVP is not your vibe, then I recommend Beauty & Essex at The Cosmopolitan. This is a spot that started in NYC (on Essex Street) and has made its way to Sin City. In the NYC location, you enter through what looks like a pawn shop and there is champagne poured in the bathroom. The Las Vegas location is located on the mezzanine level of The Cosmopolitan, so it doesn’t quite have the same speakeasy vibes, but the food and drinks are just as good. If you are looking for imaginative small plates to share, this is for you!

If Beauty & Essex sounds like something you want to try, but also want to check out LVP, you can always have a drink at Vanderpump Cocktail Garden at Caesar’s Palace before dinner. The bonus if you go this route is that you can stop by Dominque Ansel at Caesar’s and pick up some pastries. Yes, he’s known as the inventor of the Cronut, but actually, his Kouign Amann is amazing! Probably the best I’ve had, and I’ve had a few in my day.

Day Three | Back to the South End

Day

After two days of walking the strip, it’s time to take a little break. We’ll have breakfast at Salt & Ivy at the hotel, which has a beautiful outdoor patio, great food, and amazing drinks. Seriously, I ate here twice on my last trip and loved everything. Then, because the pool at Bellagio is a little more relaxed, we’ll head there for a pool day. If you reserve a chair in advance you don’t need to be a guest at the hotel and you’ll have food and beverage service. It’s delightful! Before settling in make sure you check out the Conservatory & Botanical Gardens which is beautiful and changes seasonally.

Night

After the pool, you’ll want to go back to the hotel and shower, which works out great because that’s where dinner is as well! Bring your appetite to Din Tai Fung, a Chinese chain that has won Michelin stars in Hong Kong. The food is fresh (you can see them making it in the window) and everything is amazing. Seriously, it’s hard to pick a favorite thing. Your belly will be full so, if you’d like, spend your last evening trying your hand with lady luck and checking out what the casino has in store.

Transportation

How to Get There

Las Vegas has a pretty large airport with most major cities offering direct flights which is the way I always get there. Since it is part of the 48 states, you can also drive which can be convenient depending on where you are coming from. It’s about a four-hour drive from Los Angeles.

How to Get Around

Las Vegas is very driveable so renting a car is always an option. I generally use Uber and Lyft when I’m there because then I don’t have to mess around with parking and there are always tons of cars available. The one thing to note in the casinos is there are usually designated pick-up spots that might be a little walk away so make sure to look for signs.

What to Pack

Bring layers! Which layers to bring will depend on which season you are visiting. Don’t forget that Vegas is in the desert so night will be considerably cooler than the day.

Since everything is on the strip you may find yourself hopping from one location to the next and before you know it you’ve walked 10,000 steps. Bring comfortable, but cute, shoes.

SPF, and I cannot stress this enough especially if you haven’t seen the sun in many months. The last time I was there I used 50 and was good, never got burnt, but it was so hot I did get a heat rash. The sun is no joke.

Tips for Visiting

• Stop by CVS and pick up some bottles of water and snacks for the hotel room. The mini-bar pricing is no joke! I have no problem paying more for delicious, quality food, but paying $7 for a bottle of water is just paying for convenience. Do yourself a favor, make a CVS stop on your first day there, and thank me later.
• If you will be gambling I suggest you stop by the casino desk and get a loyalty card to put in the machine. Yes, it’s basically so the casino can track your spending and what you are doing, but you can receive perks like being first in line for dinner or even free hotel stays

Other Recommendations

The above Las Vegas itinerary is what I suggest if you want to have an enjoyable time that is balanced with exploring the strip and relaxing but feel free to adjust as needed. Below are a couple of things that I also recommend, but just didn’t make it into the three-day itinerary.

• Spa Day | I love a spa day and on the off chance you are there when it’s raining (or maybe it’s too hot for the pool) the Aria spa is amazing!
• Las Vegas Sign | In all the many times I’ve visited I’ve never seen the sign. It is iconic and signifies the beginning of The Strip, but in the age of social media, there is usually a line to take a photo. If you want to do this the best bet is to go early, when the people who stayed out all night are sleeping in. If you are coming from the East and have the advantage of the time change on your side, take an Uber the second morning there and grab yourself a picture!
• Neon Museum (at night!) | Vegas has a ton of Neon signage and the Neon Museum is where those signs go when they retire.
• Buffets | I’m not a buffet girlie but if you are, Vegas is the place for it! Bellagio and Cosmopolitan are known to have two of the best buffets on the strip.
• Pinball Hall of Fame | Part museum, part arcade, you can take an Uber and find tons of pinball games to play!
• If you don’t live near an In-N-Out Burger or have never had it, there is one on The Linq Promenade. You might love it or not, but you should at least try it since so many people say it’s their favorite fast casual burger. Take it from me and get the fries well done.

FAQ

• Is it worth going to Vegas for three days?
  • Yes! Vegas can be sensory overload from all the people, the variety of noises, and the neon lights. It can be relaxing if you do it a certain way, but the stereotypical Vegas experience is best in small doses.
• Are three nights in Vegas enough?
  • Yes! 4 days and three nights are enough. If the first and last days are travel days then you have two full, non-travel days and nights. Take in a show, do a little gambling, make some dinner reservations, walk the strip, get a massage, or lay by the pool. All the details are in the above post but you can experience an amazing time in Vegas in three nights.
• How many days are sufficient in Las Vegas?
  • Have you seen The Hangover? I kid, I kid. TBH for me it kind of depends on the flight time. If you are nearby and travel time is short and can spend three days and two nights, you’ll have a fun time in Vegas. If you are like me and it’s a four-hour flight, you may want to extend it to four days and three nights. If you find yourself with more time you may want to take a day trip to the Grand Canyon or Zion National Park. Alternatively, you can stay in Las Vegas proper but spend a day in old Vegas which has a completely different vibe than The Strip.
• How much is a trip to Vegas for three days?
  • The age-old question of how much travel costs. The great thing about Vegas is that it caters to every type of traveler. You can fly an ultra-low-cost airline and stay in a basic hotel room and it can be quite affordable, eating In & Out to your heart’s desire. On the other hand, you can fly business class, stay in a five-star hotel and make fancy reservations. How you choose to travel is up to you!

Book a Trip to Las Vegas!

I typically book directly with the airline and hotel, but sites like skyscanner.com and booking.com are great for comparing options. Click the links below to book now!

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

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First things first, there are some criteria for why we chose Sedona and why it could be an excellent option for you as well:

• Easy to Get To – Since we were coming from different parts of the United States, the location needed to be easy to get to from most major U.S. cities. Sedona checks that mark as it’s about a two-hour drive from Phoneix.
• Climate – Especially during a Chicago winter, but really anytime, if you are able to change climates on vacation it adds to the energy of being in a different place. Trust there is no red rock on Michigan Avenue.
• Girls Trip – It might be repetitive to say that the criteria for a girl’s trip are that it’s good for a girl’s trip, but we wanted to pick a place that fit our needs. That is to say, not choosing a place where it’s primarily couples or the rooms are all one king-size bed. We had no problem finding a room with two queen beds, and our jeep tour was made up solely of groups of friends on girls’ trips. Similarly, during our pool day, we also made vacation friends with other girls on a girl’s trip.

Not planning a trip with your friends? Don’t worry! This Sedona itinerary is also perfect for a trip with your significant other, other couples, or family (although I have zero recommendations on a trip with kids).

It’s probably a good time to just clarify, Sedona in Arizona is not to be confused with Sonoma in California. They sound pretty similar and are both perfect for girls’ trips, but that’s a very different itinerary. Have a great trip!

If you buy something through my links, I may earn a small commission at no additional cost to you. I appreciate your support! See disclosure for details.

What is Sedona Know For?

Sedona is a city located in the U.S. state of Arizona. According to Wikipedia, it has a “temperate semi-arid climate”. What that means in layman’s terms is that it has four relatively mild seasons. You can visibly see the landscape and vegetation change as you drive from Phoneix in the Valley of the Sun, to Sedona which sits 4500 above sea level amongst red rocks.

In order to make the most out of your first visit to Sedona, you have to know what it’s known for. When in Rome…amiright?

• Hiking – When you think of Sedona you probably visualize gorgeous red rock formations. Sedona is home to Coconino National Forest, Red Rock State Park, and Slide Rock State Park. Rumor has it there are over 200 hiking trails in Sedona, so there are plenty of options depending on the length and difficulty of the hike you are looking for. I highly recommend downloading the AllTrails App on your phone to filter on different hikes and current conditions. We used it a ton to read current reviews to know if a hike was going to be icy, muddy, or in excellent condition.
• Vortex – Sedona is known for its energy vortexes, which many call spiritual vortexes. Many come to Sedona looking for spiritual healing or to find a sense of peace. Are the vortexes a naturally occurring phenomenon or just some wishful legend? I’ll let you be the judge since one is included in the itinerary below.
• Prickly Pear – Prickly Pear is a vibrant fruit from a cactus local to Sedona. If you visit May-July you’ll see the flowers bloom on the cactus that will eventually turn into fruit. All year long you’ll find this flavor all over the area, especially in beverages.

Can’t Miss Things To Do (we are Very Obsessed!)

Top three things from this Sedona Itinerary:

• Devil’s Bridge Hike
• Dinner at Mariposa
• Off-road Jeep Tour

Itinerary Overview

Where to Stay

We did a ton of research to find the perfect spot and I absolutely recommend the four-star Amara Resort & Spa. Check out my complete Amara Resort post for a full review!

You cannot beat the location of the hotel since it’s situated on the main street of Uptown Sedona. It makes it so easy to walk and explore the adorable town.

The hotel was recently renovated in 2021 and it shows! Every room has a patio or balcony, with some even facing red rocks. There is a pretty good-sized walk-in closet, enough for both of us to use. Like any good hotel, robes, and slippers are provided, and the mini bar got plenty of use.

The hotel has a ton of amenities! It’s located at the base of a short drive and is directly on Oak Creek. Once you arrive at the front door you are greeted by valet which is included in the stay.

Along with the heated outdoor infinity pool, there is a hot tub, access to Oak Creek, outdoor firepits, and cornhole boards. Across from the hotel is the spa, which I didn’t get a chance to use, but was planning on if the forecast called for rain. There is also a gym (which I didn’t go to because that’s not what I do on vacay) and a meditation room.

Saltrock Kitchen is located in the hotel, so it’s very convenient. One of the best perks was the wonderful concierge. Teah sent a long email with recommendations and was able to answer any and all questions we had. She even made dinner reservations for us and arranged the Jeep tour to pick us up at the hotel. From the moment we arrived (complimentary glass of champagne) to the moment we left (water for the car ride back) we truly felt like we were taken care of, and I absolutely cannot say that for every four star hotel.

Day One | Wander and Chill

Day

If you are familiar with a Very Obsessed itinerary you know that most coffee shops I recommend serve local coffee, but sometimes location wins. Before and After Java Cafe is located at the end of the main strip in Uptown, route 89A, so it’s the perfect spot to grab breakfast. They serve Starbucks, and there’s something comforting about a familiar menu, right? You can also grab a view of red rocks, and that just won’t get old.

Take this time to walk up and down the strip, popping into the boutiques. Some are more touristy than others, that’s to be expected, but there are some real gems. I particularly love Red Rock Apothecary (a great place for gifts) and Sedona Crystal Vortex has about every crystal you can imagine. This would be a good time to buy some crystals, if you believe in that sort of thing, to charge them at the vortex tomorrow.

Chapel of the Holy Cross is about a ten-minute drive from the hotel and is next on the itinerary. It’s very unique because the chapel is built right into the red rocks, so even if churches aren’t your thing, it’s really cool to see. The chapel is open from 9-5 every day so keep that in mind if you want to go inside. Otherwise, you should definitely at least drive past to see it.

Night

The Vault Uptown is tonight’s dinner and is a ten-minute walk from Amara. Remember how I mentioned that Amara is down a short drive? It’s short but steep so it’s great that the hotel will take you up to the main strip via golf cart. We definitely used that feature!

Day Two | Take a Hike!

Day

Cuptown Coffee is a seven-minute walk from the hotel, but I suggest getting in your car and driving and then you can head hiking afterward. They have a decent-sized parking lot so that shouldn’t be an issue depending on what time you get there and they brew coffee locally roasted in Flagstaff. While they don’t have warm breakfasts available, the pastry offering includes regular, gluten-free, and vegan. I have to say the blueberry muffin is pretty tasty.

Post coffee, drive to Posse Grounds Park & Ride to catch the Sedona Shuttle which will take you to the Dry Creek Vista trailhead to hike Devil’s Bridge. The shuttle is amazing! It runs Thursday-Sunday year-round and is 100% free. Parking is pretty limited at the trailhead so it’s nice not to have to waste time driving around looking for parking at the most popular hiking spots.

There are a ton of blog posts that go into more detail about Devil’s Bridge, so I won’t do that, but I’ll note a few things:

• You can absolutely wear sneakers, but they should be high-quality with lots of traction.
• The official hike is 2 miles but with a high clearance off-road vehicle allowing you to park at the trailhead. Otherwise, you’ll start at the Chuck Wagon trail which makes the hike 3.9 miles.
• Devil’s Bridge is Moderate Difficulty, but the majority of it is pretty easy. There are a few steep spots and some rock scrambling which is what makes it a little moderate.
• Dress in layers, cooler than you think you’ll need. It was in the 50s and my lightest layer was a long sleeve top. I was sweating.
• Take all the pictures!!!

After Devil’s Bridge, take the shuttle back to the car and drive to Boynton Vista so you can experience a Vortex. You might be tired after Devil’s Bridge so it’s great that it’s only about a 15-minute hike to get to Boynton Vortex and then you can sit, charge your crystals, and soak in the energy. Be careful not to confuse this with Boynton Canyon. They have the same trailhead, but if you make a left at the fork you’ll be on the path to hike the 6.1-mile hike (which I’ve heard is also great, but won’t take you to the Vortex).

Night

Time to go back to the hotel and clean up for dinner at Mariposa! This Latin-inspired grill, steakhouse to be more exact, has a beautiful view of the red rocks and the food and drinks are exceptional! Don’t miss the lobster mashed potatoes (featured on The Food Network) or Lisa’s Chopped Goddess salad. This was by far our favorite meal, but it can be a little tricky to get reservations. I suggest setting up a notification on Open Table and watching that like a hawk, it will be worth it!

Day Three | Off-Roading Time

Day

Start the day off with breakfast at Saltrock Kitchen in the hotel. Truth be told, we had dinner here and we had breakfast here and breakfast was much better. Next, it’s time to go off-roading Have the hotel book your Safari Jeep Tour and the Jeep will pick you up at the hotel! We did the Outlaw Trail, which takes about 3 hours and goes off-roading near the Honanki and Palatki Ruins. I learned a ton from the guide. Note, it’s a moderate trail and can get pretty bumpy. My advice is to make sure your seatbelt is tight and lean into being thrown around like a ragdoll. If you have any sort of back issue, I might sit this one out.

Once the Jeep drops you off back at the hotel you can explore more of the town (last chance for souvenir shopping), or grab a cocktail at the bar and make your way to the pool for some well-earned vitamin D time. We didn’t get a chance to do an Aura reading, but if you’re interested, now would be a great time! Sedona Crystal Vortex offers them at their second location, which is where my plan was to go if we had time. Coming from Chicago, I enjoyed the hot tub a little too much.

Night

The final night will be low key and dinner is at Sedona Pizza and Pasta Company. It’s a 5-minute walk from the hotel, or they can drive you in the golf cart basically to the front door. You can either stay and enjoy your pizza with a view of the red rocks or decide to carry out and have a girl’s night in for your last night as we did.

Transportation

How to Get There

Phoenix is the closest major city to fly into, which is pretty accessible from most major U.S. cities. In no traffic, it takes about 2 hours to drive the 120 miles between the two destinations. I recommend renting a car at the airport and driving since it will be most convenient to drive yourself around Sedona as well.

How to Get Around

Since Amara on right off the main street of Uptown Sedona, there is plenty of walking around you can do to explore the town, but you’ll need to drive to the hikes or the Sedona Shuttle Park and Ride. This is why I suggest renting a car at the Phoenix Airport to use for the duration of your trip. We rented a car at the airport, drove to Sedona, around the area hiking and back, and used about half a tank of gas.

I never suggest drinking and driving and Mariposa has excellent cocktails and is a 30-minute walk so you may want to get an Uber/Lyft/Taxi. While Sedona has Uber and Lyft (like most of the U.S.) we were told by the hotel that they were not always so reliable and they gave us a list of local taxis. We called the first one on the list and he was able to pick us up with 45 minutes’ notice and picked us up after dinner to take us back to the hotel. Note he did not have a card reader so make sure you have cash if you go this route. Since it was a flat $10 fee luckily we had enough on us between the two of us (because who carries cash anymore?)

What to Pack

I cannot stress this enough, bring layers, layers, and more layers. As I mentioned, 50 degrees in Sedona is not the same as 50 degrees in Chicago. You just never know exactly how you are going to feel.

Overall Sedona is pretty casual and even dining at Mariposa I felt completely comfortable in a pair of black jeans and a nice sweater. With that being said, I’m not going to get into a full packing list (although let me know in the comments if you’d like one) with x amount of t-shirts, leggings, etc. but below are just a few things to keep in mind:

Unless you will be hiking on difficult paths, you should be fine hiking in high-quality sneakers with lots of traction.

You will want to bring water with you on your hikes. If you are not a backpack girlie, like I’m not a backpack girlie, I loved this water bottle sling. It’s an adjustable cross-body strap, so it’s comfortable, and it has an extra pocket for your phone, lip gloss, hand sanitizer, etc.

It might still be “cold” when you visit but bring a swimsuit to experience Amara’s heated pool and hot tub. The resort provides slippers if you don’t have enough room in your bag for slides.

Tips for Visiting

• If you have crystals already, remember to bring them with you to Sedona to charge them at a Vortex!
• There isn’t a convenience store or bodega on the main street, so if you have a late-night chocolate craving you are at the mercy of the minibar. I suggest bringing something with you or stopping at a store before checking into the hotel.

FAQ

• How many days in Sedona do you need?
  • Entirely depends because in 3 days you get a good feel for the town, hiking, and relaxing. If you want to do multiple days of hiking then you’ll need more days, and there are so many hikes you can do. You’ll want to be honest with yourself about the types of hikes you want to do and your physical fitness level. For instance, if you aren’t in the best shape, and do a moderately difficult hike, you may be too sore to go hiking the next day. If you are in moderate shape and want to stick to a lot of easy hikes then you would definitely be able to do multiple days. There are also many day trips you can go on, like to Flagstaff or the Grand Canyon.
• Are 3 days in Sedona enough?
  • It is, we had two full days and two travel days, so let’s call those two travel days one full day, hence equaling 3 days. Just be mindful of the times when you are traveling. For instance, if you are going to consider your travel day a visiting day, but don’t land in Phoneix until 7 pm, that won’t give you any exploring time. Remember you’ll need to pick up the rental car and drive the two hours to Sedona.
• How Do I spend 4 Days in Sedona?
  • Either go on another hike (I really wanted to do Cathedral Rock) or take a day trip to Flagstaff or the Grand Canyon. You could also plan for a Spa if there is one day that will be rainy.
• What is the best month to visit Sedona?
  • The end of February for President’s Day weekend was ideal. It’s not peak season, which is March-May, and not sweltering. There is somewhat of a risk during this time though because we had perfect weather in the high 50s and it was sunny, but the day after we left they were forecasting snow.

Book a Trip to Sedona!

I almost always book directly with the airline or hotel I’m using, but sites like skyscanner.com and booking.com are great for comparing options. Click the links below to book now!

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

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The post Sedona Itinerary appeared first on Very Obsessed.

Before we jump in, let’s review some of the things Québec is known for since they will be sprinkled throughout. If you go somewhere and they are known for something, you should have that thing. I learned this lesson hard way when I went to a gelato place in Venice and had the worst sandwich of my life, but that’s a story for a different day.

• Poutine – French Fries, Cheese Curds (fresh, not fried), and Gravy. Those three components are standard in this famous Canadian dish, but many variations exist.
• Maple Syrup – Canada produces 85% of the world’s maple syrup. You can’t get much more known for something than that.
• Beer – According to Wikipedia, “Beer was first introduced to Canada by European settlers in the seventeenth century, as Canada had an ideal climate for making beer before refrigeration was introduced.” So there you have it.

If you buy something through my links, I may earn a small commission at no additional cost to you. I appreciate your support! See disclosure for details.

Where is Québec City?

Québec City is located in the French-speaking Canadian province of Québec. Technically Québec City is just “Quebec” but since the province has the same name, most refer to it as Quebec City to distinguish the city from the province. Confused?

The nearest major city is Montreal, which is about 160 miles away. Montreal is major in that 1.8 million people live there, but Québec City isn’t a small town by any means. Québec City’s population is around 500,000, but don’t let that cloud the storybook visions in your head. We will focus most of our time on the itinerary in Old Québec, a historic UNESCO World Heritage Site made of pubs, shops, and cobblestone streets along the Saint Lawrence river.

Can’t Miss Things To Do (aka Very Obsessed!)

Top three things from this Winter Itinerary:

• Québec City German Christmas Market
• La Souche Microbrasserie
• Pub L’Oncle Antoine

Itinerary Overview

Where to Stay

When I started planning my Québec City trip there was only one place I had in mind to stay, and that’s the world-renowned Fairmont Le Chateau Frontenac. As the only 5-star hotel in Old Québec, this is the place to stay if you like luxury and want to be in the center of it all. Dufferin Terrace, the wooden boardwalk that borders the Saint Lawrence River (and also has Tobogganing starting mid-December) runs along the hotel. Allegedly the Fairmont Le Chateau Frontenac is the most photographed hotel in the world, and it’s easy to see why. The hotel looks like something straight out of a movie, high on a hill in the style of a french castle.

If you visit during Christmas the hotel has common areas decorated beautifully with Christmas trees. and lights, and we even had a Poinsettia in our room. Fairmont Le Chateau Frontenac has everything you would expect from a 5 star hotel (outlets near the bed, full-length mirror, plenty of room to sit and for the luggage to be off the floor), and the Le Labo toiletries are divine! Plus they offer lots of other complimentary perks that we didn’t take advantage of, but there is room in the itinerary so you can (like wine tasting, a tour of the hotel, etc.)

I have friends who have stayed in an Airbnb in Quebec City previously and they agreed that it was great to be in the middle of the magic. My advice is to book the hotel early before everyone starts thinking about Christmas in QC and the prices go up. I booked the hotel in July and the trip wasn’t until December. The prices were much more affordable than I typically expect from a 5-star hotel.

Day One | Today is all about Old Québec

Day

When I visit a new city I love to try out their local coffee, so a stop at Café La Maison Smith is in order! Their pastries are solid (Pain au Chocolate was my favorite that I tried) but their coffee is very good. They brew it themselves and even ship it to the U.S. if you are so inclined. They have a few locations; Des Jardins is closest to the hotel and has a bit more seating, and Notre Dame is the original location and is located near Place Royale, a historic cobblestoned square (we’ll be visiting on day three).

Next, we’ll roam around the city, on the picturesque Quartier Petit Champlain. No chains here! This street is like walking the old roads of a storybook European town, with local shops and restaurants. This is where we’ll stop for some lunch and beverages (I highly recommend the Caribou) at Pub Borgia. When you walk in you are faced with the aromatic scent of caramelized onion and this allegedly has the best French Onion soup in the city. If you want to stay a while feel free and play one of the many board games that are offered.

Old Québec is split into Upper and Lower and while you can walk the many steps connecting the two, you may want to try the Funiculaire. This railway (but more like a tram) is under $3 CAD and can take you up or down the 59 meters.

Night

The Québec City Christmas Market is split into 5 different locations, which really helps with traffic control and doesn’t seem overwhelming at all. I would, however, suggest not trying to visit all locations in one day. Today visit the closest sites to Old Québec, and we’ll visit Place D’Youville at the far end of day three. Note, the Christmas Market is free to visit, and most booths accept credit cards.

Dinner is at Le Chic Shack, a fast-casual restaurant near the hotel that specializes in burgers, poutine, and boozy shakes.

Day Two | Get into the Neighborhoods on a Brewery Crawl

Day

Free time before making our way to the Saint-Jean-Baptiste neighborhood. Le Projet Microbrasserie is a gastropub that offers a full menu and over 30 beers from various breweries around the city. Once you’ve had a pint (or two or three) take some time to explore Rue Saint-Jean, a bustling street full of eclectic shops.

Next, we are on our way to one of my favorite breweries, Noctem, and it’s not just because it’s black cat themed (although that’s a fun bonus). It’s a 12-minute walk or a 5-minute drive from Saint-Jean-Baptiste so very walkable if not too cold. Noctem is popular so you may want to try to make a reservation. We wandered in and they were very accommodating, but let us know upfront the table was reserved in 2 hours, which was more than enough time to try a flight.

Night

We’ll now make our way to the Limoilou neighborhood for a cozy spot to grab dinner. Limoilou is about a 25-minute walk from Noctem, or a 5-minute drive so I would take an Uber here. La Souche has a variety of beers but their food menu is great. While I’m not a poutine fan (no squeaky curds for me) everyone I was with agreed they have the best poutine in all of Québec City! They offer a few variations and the beer is exceptional!

It’s been a long (boozy) day of exploring so it’s back to the hotel for a nightcap. 1608 Bar is a vibey cocktail lounge in the Frontenac that has theatric drinks and serves complimentary snacks. It’s not inexpensive, but it’s a delightful way to end the evening.

Day Three | A Little Culture in Old Québec

Day

Start the day off with brunch at Cochon Dingue. With multiple locations, the closest spot to the hotel will be a 7-minute walk to the Champlain location. Get your belly full because it’s time to explore the Museum of Civilization. Don’t let what it looks like from the outside deceive you, it’s much larger than you think! Not only is there a great exhibit on the history of Quebec City, but they also have rotating eclectic exhibits as well.

Remember when I said we would visit the Place Royale? Now is the time! After the museum walk back towards the hotel and you’ll run into the historic cobblestoned square with a beautiful oversized Christmas tree right in the center. Pop into Pub L’Oncle Antoine and warm yourself with mulled wine in this 17th-century brick cellar-turned-pub.

Night

Quebec City is the only fortified city north of Mexico, and walking the ramparts is like taking a step back in time. There are four main gates, and we’ll start our evening at the Christmas Market near Saint-Jean Gate. Sitting right outside of the gate is the furthest Christmas market and an ice skating rink at Place D’Youville. There is no admission fee to skate and they rent skates so it makes for a fun winter activity! When we are done skating we make our way to dinner at Maison Livernois while visiting the Christmas Market booths along the way. Although Maison Livernois is a vibey little spot, it’s totally acceptable to wear jeans. They have great apps and cocktails (known for their gin) and will be an 8-minute walk back to the hotel to get a good night’s sleep before flying out tomorrow!

Transportation

How to Get There

Plane, train, or automobile, that is always the question, isn’t it? Unless you are close or have a ton of time, flying to Québec is going to be your best bet. Most major cities have direct flights to Montreal, which means you can have that be your final destination and drive or take a train to Quebec City. Since Quebec City has a decent-sized airport I chose to fly Air Canada (part of Star Alliance) into Québec City with a layover in Montreal. The drive is a little under 3 hours and the flight from Montreal to Québec City is a little over an hour. Totally your call!

How to Get Around

Québec City is very much a walking city, although it is Hilly with a capital H. To go from Old Quebec to the neighborhoods it’s better off driving, but because there are pubs and breweries on the itinerary, I highly suggest taking an Uber or Taxi.

One thing to note, Uber’s are not nearly as available in Québec City as they are in the US, and based on the vehicle we received from the airport to the hotel, I don’t believe they have the same standard of XL either. It is not uncommon to wait 20 minutes for an Uber while you are in Old Québec or a neighborhood, so just plan that in advance if you have to be somewhere (dinner reservations).

What to Pack

Like any cold climate city, the weather can be unpredictable. When I was there in December the temperatures ranged from mid 30’s Fahrenheit to single digits, without wind chill. As someone who HATES the cold (I know, I know, Canada in Winter) I highly suggest bringing layers. Also a high-quality winter coat (mine has to have a hood), gloves, a hat, and a scarf.

Québec City is a walking city, as mentioned earlier, but it’s very hilly, so bring shoes you can walk a lot in, that are comfortable, and that have good tread (hills can get slippery in the snow). I wore lug sole boots most of the time because they are warm, comfortable, and waterproof. I just also made sure to wear them on the plane so they didn’t take up a lot of room in my luggage.

Quebec City is a casual city, so you’ll be fine wearing jeans pretty much everywhere. My go-to is black since it’s a little more elevated than blue, but still warm when that wind is whipping.

Tips for Visiting

• French is the official language, but most people speak English as well. Only some websites will be available in English, which goes for the QR menu. If you are using an iPhone hit the translate button in the URL and the menu will be translated into English.
• The Canadian Dollar, CAD, is the national currency but I found everywhere to accept credit cards. In my International Travel Tips Guide I reiterate, if the credit card slip asks if you want it in USD or CAD, always choose the native currency.
• Because Canada isn’t part of the US, they are on the Celsius scale. I could tell you how to convert, but it’s easier to use your phone. Just know that 0 degrees Celsius is freezing (32 degrees Fahrenheit) so there’s a big difference.
• Since Canada is in North America luckily the voltage is the same which means your blow dryer, flat iron, and Air Wrap will all work without converting!
• Depending on your cell phone provider, you may or may not automatically have service. As part of my plan, I have service automatically in Mexico and Canada, so my phone worked immediately after departing the plane at no extra charge. Just note, I was on 3G for a lot of the trip so it’s not as fast as we may be used to.
  • My friend’s plan didn’t automatically have international service but almost everywhere offers free Wi-Fi so it was no problem. If no one you are traveling with will have service, and you want to call an Uber on the side of the road it could present a problem. In this instance, I recommend contacting your service provider and adding Canada.

Book a Trip to Québec City!

I almost always book directly with the airline or hotel I’m using, but sites like skyscanner.com and booking.com are great for comparing options. Click the links below to book now!

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Is Chicago Worth a Trip?

Absolutely! You may have heard that Chicago is dangerous. Yes, it does have its fair share of crime, so does any major city. It’s about being a smart traveler and being aware of your surroundings and you’ll have a good time. I

Chicago is the 3rd largest city in the US, and with two airports it’s incredibly convenient to get to. It’s been ranked “Best Restaurant City” by Bon Appétit magazine and the 2nd best city in the world by Timeout. Chicago has Midwest hospitality, it’s easy to navigate, there are tons of shopping and restaurants, it’s got a beautiful (Great) lakefront, and the list goes on and on.

How to Get to Chicago?

Since Chicago is located in the middle of the United States the city is easily accessible via plane, train, or automobile.

Chicago is home to two major airports. Chicago O’Hare is the larger and busier of the two airports and Midway is a little more manageable, although doesn’t have as many options. Both have the “L”, the elevated train rapid transit system, that runs directly from the airport straight into downtown if you want don’t want to deal with traffic.

Union Station in the West Loop is where the Amtrak arrives so if train travel is more your style it will take you straight downtown.

Check out my post on how to get around downtown Chicago.

Where to Stay in Chicago?

Since short-term rentals are legal, there is no shortage of VRBO listings to experience Chicago like a local, but I’m partial to hotels. Chicago has a ton of great hotels, this post has my full list of coolest hotels in The Windy City, and below are my top picks for your first visit.

The Langham Chicago | A 5-star hotel right on the Chicago river, it’s luxurious, has great views, and has a central location. If you need a little pampering the spa is amazing with great massages and hydrafacials!

The Drake Hotel | This 4-star hotel is rich with Chicago history, over 100 years old, but still feels as elegant as ever. Plus, it’s on the mag mile and Lake Michigan. Try the high tea in the Palm Court during the day, or cocktails and dancing at Coq D’or.

Viceroy Chicago | This is where the cool kids stay! It’s a 5-star hotel, with a great location, and an outdoor rooftop pool (need I say more).

Day One | Chicago 101

Day:

Start the day strong with brunch at Etta. Etta is a modern Italian restaurant and one of my favorite dinner restaurants in Chicago, but brunch is equally amazing. Do not miss the focaccia with whipped ricotta and get a pizza for the table, just trust me on this one. Etta has two locations but for this itinerary you’ll go to the River North location.

After brunch take a Lyft to Navy Pier. Yes, it is touristy, but you’ll get a great view of the city and you can’t visit Chicago without taking a ride on the Ferris Wheel (it was built for the Chicago World’s Fair after all). Navy Pier is also home to Offshore Rooftop, the largest rooftop deck in the U.S. If you are going to Navy Pier just for Offshore though I recommend you check out the website first as they are often closed for private events.

Now that you’ve experienced a little bit of the lake, it’s time to check out the river. Take a Lyft to the corner of Michigan Ave and E Waker Driver for an Architectural Boat Tour from the Chicago Architecture Center. You may not know about Chicago architecture before arriving, but you’ll be surprised at how rich with architectural history Chicago is.

When the tour is over, walk along the Chicago Riverwalk on the Chicago River. It’s a little over a mile long but you don’t need to walk the full length. There are bars and restaurants to stop along with a way to get a glass of wine, a snack, and do a little people-watching. The soft pretzel at Northman Beer & Cider garden is actually pretty good!

Night:

You can’t come to Chicago for the first time without trying deep-dish pizza. My favorite place that is the most accessible is Lou Malnati’s, and they just opened a location on Michigan Ave! Get the butter crust, get the Malnati’s salad, and thank me later. But you had pizza with brunch and now dinner you say? Welcome to Chicago.

Finish your night at The Second City, the world-renowned sketch comedy and improv club. I like to go to the latest show, the comedy is a little looser then. They offer a few different shows so read the descriptions and pick which one is most interesting to you. With talents like Aidy Bryant, Tina Fey, and Steve Carrell coming out of it, you can’t go wrong with any choice.

Day Two | Bougie Chicago

Day:

I hope you aren’t afraid of heights because Willis Tower, locally known as the Sears Tower, has a Skydeck that everyone must visit at least once. It’s the third tallest building in the Western Hemisphere, but the real star of the show is The Ledge. The Ledge is actually a glass box you stand in that goes 4 feet out from the building, and is 103 stories high. Cue stomach drop.

Now that your stomach is settled time for brunch and some more amazing, although much more manageable, views at Cindy’s Rooftop on Michigan Ave. The rooftop has a retractable roof and a terrace (with firepits when it’s chilly) so you can dine no matter the weather. The view is of Lake Michigan, Millenium Park, and “The Bean”, your next destination.

Cloud Gate, aka “The Bean” is located in Millenium Park and is quite a tourist destination. Truth be told, it will be busy and you won’t need much time there, but you have to at least check it out.

Take a five-minute walk to The Art Institute of Chicago, one of the country’s oldest art museums, and check out the works of Van Gogh, Monet, and Picasso

Night:

Get ready for a night on the town!

In the Midwest we know steak, but that doesn’t mean you need to go to an old-school steakhouse. Maple & Ash is a scene, is the best possible way. You’ll drop a pretty petty here, but the vibe is cool, the food is amazing, and you’ll feel like you are celebrating something, even if it’s just going on vacation!

The Chicago Magic Lounge is a hidden gem because it’s not in a part of town where tourists go, but it’s a local favorite. Enter through a faux laundromat and enter into a Gatsby-era speakeasy lounge with a close-up magic show. It’s an experience unlike I’ve had anywhere else.

When to Visit Chicago

Chicago is a city with four distinct seasons and they all have their high points, but nothing compares to Chicago in the Summer. Spring and Fall are also really great, but you risk a bit of rain in the Spring or an early cold front in the Fall.

If you chance it and come in Winter you’ll have to substitute some things on the itinerary (let me know if you do and I’ll give you recommendations) and don’t be surprised if your flight is impacted by snow.

Only 1 Day in Chicago?

If you only have one day in Chicago (boo!) do the Day One itinerary. It really is Chicago 101. If it happens to be raining on your one day in Chicago, sub the day portion of Day Two and stick with the night portion of Day One.

What is There To Do in Chicago For 3 Days?

Wondering how many days are needed in Chicago? I prefer two nights, three days the first time I visit a new city. That way I have one full day and night that isn’t a travel day, but if it’s not for me I haven’t committed too much time. You’ll get to see a lot of Chicago in this time frame and won’t be bored.

I have separate itineraries for the Spring/Summer and Fall. Let me know in the comments if you’d be interested in a Winter itinerary too.

Some people ask if 2 days is enough in Chicago. I love The Windy City so I’m partial, but if the option is 48 hours or nothing, definitely visit and you’ll get a good feeling for the place. If you are here longer though you won’t be bored.

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

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If you buy something through my links, I may earn a small commission at no additional cost to you. I appreciate your support! See disclosure for details.

Where is San Antonio TX?

San Antonio is the second-most populous city in Texas, located in the U.S. Some people consider this the South, some the Southwest, and some consider Texas a region of its own.

The city’s location within Texas is towards the south and in the center of the state, about 80 miles SW of Austin and 200 miles due West of Houston. Because of this close proximity, San Antonio is the most visited city by Texans themselves.

San Antonio has been designed with the downtown in the middle of an interstate loop, I-410. I’ve created this itinerary to remain within Loop 410 so that there isn’t a ton of time spent driving. If you visit San Antonio for a second time, there is a lot to do and restaurants to visit that are outside of the loop (let me know if you are interested in recommendations for that). Texas is sprawling and there is a lot of land, San Antonio is no different, even though it is a city.

This San Antonio 3 day itinerary should keep you busy, but with plenty of time to wander and explore, without spending too much time in the car.

Day One | Downtown San Antonio

Day

Brunch will be at Snooze located in the Alamo Quarry Market on the northern side of San Antonio. Now this is a mid-size chain but they are only located in a few states in the U.S. (we don’t have them in Illinois) and they are delicious. If you have one near you, or you just want to go someplace local, go to Guenther House instead.

Back to Snooze, they have a wide menu so everyone will find something, great cocktails, but the star of the show is you can get a pancake flight. That’s right. A pancake flight.

After brunch, go back downtown and visit The Alamo, it’s probably the most historic place San Antonio is known for (and no there is no basement). For those that claim there is no history to the U.S, the Alamo dates back to 1836. You can take a guided tour or walk around yourself. As important and iconic as The Alamo is, it’s actually not that big, so you won’t be spending a ton of time here.

Once you have gotten a chance to check out The Alamo, take this opportunity to walk along the river. San Antonio’s River Walk is a 15-mile pedestrian walkway along the San Antonio River. About 5 miles of this river runs through downtown San Antonio and is sprinkled with restaurants and shops. Note there are some tourists traps and shops filled with nothing but tchotchke’s, but just avoid those.

It’s completely free to walk and is open 365 days a year. If you have 45 minutes to spend, take a narrated river cruise, where you’ll learn all sorts of interesting things about San Antonio.

Night

You’re in Texas, and it’s time for some Mexican food. My favorite Mexican restaurant is Rosario’s Southtown location. Their chips and salsa are great and so are their margarita’s, it’s what Tex-Mex should be.

After dinner, it’s time for a show. A light show that is! The San Fernando Cathedral is located right downtown and the city projects a light show onto the facade of the building every Tuesday, Friday, Saturday and Sunday, at various times. The current show is by a French artist and is a visual representation of the history of this city. There are vendors outside so grab a glass of wine and watch the show.

Day Two | Historic King William

Day

Another day, another brunch, this time at Stella’s Public House where you can grab a mimosa flight (can you tell I love flights?

After brunch it is time to get the body moving and walk around the King William Historic District. This article from SanAntonio.Gov does a great job of explaining the history behind the district, but it’s a beautiful neighborhood with gorgeous homes and again, for those who say there is no history in the U.S., you’ll find some here.

If your trip is flexible, once a year in April, the city hosts The King William Fair, which is a big deal in the city. There’s a parade, and street performers and everyone walks around wearing a flower crown and drinking cocktails. It’s a fun time!

Night

Last night we had Mexican and tonight it’s time for BBQ. There are a lot (and I do mean a lot) of BBQ places in the city, and if you ask five people what their favorite place is you could easily get five different answers. But Dignowity Meats is a little lesser know, probably due to the location, but is amazing! I seriously crave their burnt ends.

If you haven’t been to a proper BBQ place before, do yourself a favor and look at the menu before you order. You’ll go up to the window and order your meats by the lb and your sides, and they’ll call you when it’s ready. All the seating is outdoors and they have games at the table while you wait. The food is the best! The neighborhood is safe, it’s just not the most touristy so I don’t think it gets its due. It was featured on Diners, Drive-Ins, and Dives if that gives you a vibe.

Depending on when you visit, this is the night for some real entertainment. San Antonio fiercely loves their beloved NBA Basketball team, the San Antonio Spurs. If you can catch a game, great! If not, the Majestic Theater host some of the best musicals or stand-up acts that tour the country. The theater was built in 1929, but in Spanish-style architecture, something not seen every day.

Day Three | The Pearl

Day

The Pearl is a very unique place. The former brewery turned thriving community is probably the coolest place in San Antonio. Every Saturday and Sunday they hold a Farmers Market, and that’s what is on the agenda today. Stop by Local Coffee and grab some caffeine. Then take your time enjoying wandering the Farmers Market and the entirety of The Pearl.

Once you’ve gotten your fair share of the Farmers Market, go behind Hotel Emma (more on the hotel later) and you’ll find the River Walk again. If you walk south you will walk towards downtown. It’s about a 2-mile walk on the river from The Pearl to downtown. I like to walk down and back and get a little movement in before dinner, but you do you. Note, the River Walk goes under some bridges…and sometimes there are bats. If you are like me, run!

Night

Now back at The Pearl for the last night and it’s time for Mexican Street Food at La Gloria. Sometimes there is a long wait, so be prepared. Ask to sit outside, order the Queso Fundido, a Mangonada and thank me later. The Mangonada is where I discovered my love of chamoy, in fact, it inspired my Mango Margarita recipe.

Lick Honest Ice Cream is what you’ll want to do for dessert. An ice-cream shop based in Austin, they create unique flavors but use farm-fresh ingredients. They carry dairy-free too!

Where to Stay in San Antonio

Remember how I said we would get back to Hotel Emma? Well, that’s because it’s my recommendation for where to stay. It’s at The Pearl so there are a ton of things to do right outside your doorstep and the building, which was built in 1894, is absolutely stunning.

If it’s a little outside of the budget, and your first time visiting, then I recommend choosing one of the many hotels on the River Walk. When I’m new to a city one of my biggest things is feeling safe where I am, and most often that equates to being where the people are.

San Antonio is home to some gorgeous resorts, but those are more of a drive away, in Hill Country.

How to Get Around San Antonio

As I mentioned, San Antonio is spread out geographically, just like Texas. You generally need a car to get around, but I’ve tried to keep this itinerary tight so there is minimal driving and you don’t have to rent a car if you don’t need to. The furthest place away is brunch at Snooze on the first day. If you rent a car, great! If you don’t, I’m not sure that it would be worth two Lyft rides so then I would take my Guenther House replacement suggestion.

Lyft’s and Uber’s are easy to find and that’s my preferred method of getting around (I like to enjoy a cocktail or two on vacation). Public transportation is minimal so I wouldn’t plan on using that.

When to Visit San Antonio

Contrary to what some may believe, San Antonio does have seasons. It gets cooler, sometimes cold in the Winter, and scorching hot in the summer! Spring and Fall are the best time to visit when the temperatures are pleasant and you can walk around, and dine, outside.

As mentioned above, if you are interested in visiting during King William Fair, that is in April.

Only 2 Days in San Antonio?

San Antonio can totally be done in only 2 days. In order to modify this itinerary for 2 days in San Antonio, take the morning of day 2 and the evening of day 3. Oh and on day 1 definitely dine at Guenther’s, you don’t want to drive to Snooze if you are short on time.

What is There To Do in San Antonio For 4 Days?

While there are still a ton of things to do in San Antonio, the McNay Art Museum and Fiesta Texas are just a couple, if you will be vising an extra day, I recommend getting out of the city and visiting Fredricksburg. Fredricksburg is a town about 70 miles away in Hill Country and is known for wineries and shops lined up along the main street.

If you want to be a little more active, Enchanted Rock is 17 miles north of Fredricksburg. It’s a mountain in Hill Country made of beautiful pink granite and has 11 miles worth of hiking trails, including to the summit.

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

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If you are looking for a quick list of the best Chicago has to offer, check out my Best of Chicago guide. If you are visiting in the Spring and Summer, don’t miss out on that 3 day itinerary which includes the Lakefront.

If you buy something through my links, I may earn a small commission at no additional cost to you. I appreciate your support! See disclosure for details.

Day One | Today is all about Downtown Chicago

Day

A great place to start the trip is Cindy’s Rooftop (don’t worry, it’s covered in the Fall).  Right on Michigan Avenue, you’ll be able to see Lake Michigan, Millenium Park, and the famous “Chicago Bean”.  Depending on the day of the week you’ll have lunch or brunch (only served on weekends). If you are the type of person that needs sustenance upon waking (I myself need coffee) then grab some coffee and a pastry from whatever local shop is near and then plan to go to Cindy’s for small bites.  The view is not to be missed.

After you’ve seen the city from 13 stories high, take the 5-minute walk to the Art Institue of Chicago. You’ll walk right past the Bean, whose real name is Cloud Gate, and into the second-largest art museum in North America (right behind the Metropolitan Museum of Art in New York).

Related

• Best Hotels in Chicago for every Neighborhood
• Coolest VRBOs in Chicago
• Best Brunch in Chicago

Night

Take some time to go back to the hotel and freshen up before dinner.  Tonight’s spot is Maple & Ash for some of the best food in the city. They are known for their steak, and it’s not to be missed, but everything is amazing. It’s a scene so take the opportunity to get changed and take a Lyft to dinner.  If you get there a little early, you can grab a spot at the bar and have a pre-dinner cocktail, it’s a great spot for people-watching.

After dinner, get back in the Lyft because you are going Uptown to one of my favorite spots in the city, Chicago Magic Lounge. You’ll enter through a faux laundry storefront and enter into a speakeasy-like close-up Magic Show.

Day Two | Enjoy the city like a local!

Day

Inside the Restoration Hardware in the Gold Coast is the beautiful 3 Arts Club Cafe and it’s a wonderful spot for brunch in the Fall. With its tall ceilings and tons of glass windows, you get the sense of outside but you’ll be warm and cozy before heading out for the day.

Depending on the weather you can grab a Lyft or go for a nice stroll to Lincoln Park and the Lincoln Park Zoo. It will be about a 20-minute walk to the Zoo, but you’ll hit the park after about 10 minutes from Restoration Hardware. If you aren’t sure how much time you’ll spend it’s still work visiting because it’s totally free! Some of my favorite animal exhibits are the Big Cats (they just came back after some time away for a habitat renovation), the Primates and the Bears (I just realized that was very close to Lions, and Tigers, and Bears, oh my!)

Night

You’ll dine in the Lincoln Park neighborhood and have dinner at Summer House Santa Monica, a West Coast-inspired fresh-fare restaurant. And it’s not too far from this evening’s entertainment…Second City!

If you like comedy then I’m sure some of your favorite comedians have spent some time in The Second City. That’s because it’s a world-renowned improv and comedy club that’s been around for 60 years. They offer a variety of shows on different stages so take a look and I’m sure they’ll have something to appeal to you. I’m partial to the late shows because I prefer them just a little more ‘adult’ but you do you.

Related: What to do in Milwaukee ( a quick trip from Chicago)

Day Three | Becoming a fan

Day

After two substantial brunchs, it’s time to grab a quick coffee and a pastry before you see Chicago from a different view. Depending on where your hotel or VRBO is will probably depend on where you’ll go. Some that I love are Goddess & the Baker, Big Shoulders, and Fairgrounds Cafe.

Next is the Skydeck at the Willis Tower (or as we locals still say, the Sears Tower). At 103 floors, it is the highest observation deck in the United States. If you dare, step into one of the glass boxes overhanging the building as you look down more than 1,300 feet to the ground. It’s a little terrifying, but not something you can do every day.

Then you are off to watch the Chicago Bears play some football at Soldier Field (notice I didn’t say win, I like to be realistic). Since it’s an outdoor stadium with no retractable roof, make sure to check the weather before you come to Chicago so you can pack appropriately.

Night

You can’t visit Chicago for the first time without trying deep-dish pizza. Love it or hate it, you at least need to try it, and that’s what’s for dinner.

Take a Lyft after the game and go to Lou Malnati’s. If you are visiting with enough people to order two pizza’s then you may want to get one deep dish and one thin crust, because it’s pretty good too since it has their signature butter crust. If you are craving some produce in your life the Malnati Salad is so good.

Day drinking always makes me tired (and I typically have a drink at sporting events) so I would call it an early night, knowing tomorrow is a travel day.

Related: Best Hikes Near Chicago

I hope this has been a good starting point for your Fall itinerary for Chicago.   This is by no means exhaustive and will depend a bit on the weather. If it happens to be a really nice day, I recommend an architectural boat cruise on the Chicago River or perhaps a walk along the lakefront. If you want a snack, hit up Garrett’s Popcorn or Molly’s Cupcake and you won’t be disappointed.  Make sure to check the weather and the sports schedule to see if you need to make any adjustments.  

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

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This itinerary is built by staying in a hotel in southern Sonoma County, in the city of Sonoma.  If you are staying in a different area you may want to work forward or backward, but this will give you a good insight into how I plan it. If short-term rentals are more your thing, check out this post for amazing VRBO options in Sonoma County.

Note this wine country itinerary is alcohol friendly, and California is spread out so you’ll need to drive.  With lots of options, I suggest hiring a private driver or taking a Lyft, and always remember to drink responsibly. Without further adieu, here is what to do for 3 days in Sonoma for a first time visitor.

If you buy something through my links, I may earn a small commission at no additional cost to you. I appreciate your support! See disclosure for details.

Day 1 | No time like the present to experience wine country.

Day

If you are planning on having a leisurely full day of paced drinking, I suggest having a proper breakfast so you aren’t drinking on an empty stomach.  However I usually don’t like to have anything too heavy either so a quintessential Californian breakfast is perfect, and if you are staying at El Dorado Hotel then the Kitchen there will fit the bill.

To not pack too much into the trip, I recommend only two wineries per day.  I’ve done more, oh it can be done, but for your first time, I recommend taking it a little slower. This will allow you to enjoy experiencing the vineyards, the view, and the wine.  Order some charcuterie for an afternoon snack and relax, it’s truly what Sonoma is about.

I try to group the wineries I want to visit in similar locations.  So Day 1 will stay in the more southern part of Sonoma County, and pick a couple of wineries to try there.  Some I recommend are:

• Kunde Family Winery
• B.R. Cohn Winery & Olive Oil Company
• St. Francis Winery & Vineyards
• Cline Cellars
• Gundlach Bundschu Winery

Night

If time allows (which this should) I like to take some time to go back to the hotel and freshen up before dinner.  The Girl & The Fig is back in the city of Sonoma, right on the square, a short walk from El Dorado.  It’s like a little piece of France in California and it’s so nice.

Day 2 | There’s more than wine!

Day

Today starts with a stop by Avid Coffee for a cup of caffeine and a light bite, and then off to the shore.  Which beach you pick should depend on what you want to do.  Want to go hiking?  Try Sonoma Coast State Park.  Want to go horseback riding?  Try Bodega Bay.

After expending a little energy it’s time for lunch and you probably aren’t that far away from Russian River Brewing Company.  They have two locations, one is a brewpub and one is also a brewery.  Told you there was more than wine…there’s beer!  The brewery may or may not be open due to state and local public health orders in which case stop by either location for a drink and pub fare, but if the brewery is open nothing like a good brewery tour.

If you haven’t done enough hiking for the day take a stroll through the Petrified Forest on a self-guided tour and see trees that are over 3 million years old.  There are a few of these forests in existence but the one in Sonoma County is home to the largest petrified trees in the world.

Related: How to Plan a Vacation (includes free downloadable planner)

Night

Since you’ve been communing with nature I would go back to the hotel to freshen up, which is no problem because tonight’s dinner is a 30-minute drive away.  The parking lot is small, and the inside isn’t spacious, but Wishbone is worth the wait.  The flavors are seasonal and fresh, I recommend getting a few things to share.

Day 3 | A change of scenery, more wine, naturally.

Day

The northern part of Sonoma County has a very different feel nestled among the trees and that’s where we’ll spend today.  Again, I recommend two wineries in this area, some of my northern Sonoma County winery recommendations are:

• Amista Vineyards
• Soda Rock Winery
• Sbragia Family Vineyards
• Ferrari-Carano Vineyards and Winery
• Chalk Hill Estate Winery

Night

A cool experience in wine country is to eat a luxe meal at a vineyard.  Some wineries offer private events for dinner and if you will be there during this time, book it.  If not then I would recommend having lunch at one of the wineries since most offer lunch.  If you do that then go for a lighter dinner since lunch would have been multi-course.

A multi-course meal at a winery will need to be something you book in advance so do your research on which wineries you want to go to and what days you’ll be there and see what fits with your schedule.  Some wineries that offer meals are:

• St. Francis Winery & Vineyards
• B.R.Cohn Winery & Olive Oil Company
• Simi Winery

Sonoma – Northern California’s laid-back wine country

I hope this has been a good starting point for your Sonoma County itinerary.  This is by no means exhaustive…if you don’t like wine then you can fill your days with more nature or hit up some museums.   But if wine is your thing then you can fill ALL your days with wineries.

Have a travel bug? Check out this honest Excellence Playa Mujeres review.

Wanting to try an itinerary to a new place? Try this 3 day Chicago itinerary.

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

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A perfect trip to me has a balance between seeing the sights and leaving time to explore. If you are looking for a quick list of the best Chicago has to offer, check out my Best of Chicago guide.

If you buy something through my links, I may earn a small commission at no additional cost to you. I appreciate your support! See disclosure for details.

Day One | Today is about really seeing the city.

Day

A great place to start the trip on a beautiful warm day is Cindy’s Rooftop.  Right on Michigan Avenue, you’ll be able to see Lake Michigan, Millenium Park, and the famous “Chicago Bean”.  Depending on the day of the week you’ll have lunch or brunch (only served on weekends). If you are the type of person that needs sustenance upon waking (I myself need coffee) then grab some coffee and a pastry from whatever local shop is near and then plan to go to Cindy’s for small bites.  The view is not to be missed.

After you’ve seen the city from 13 stories high, walk over to Navy Pier and take an Architectural Boat Tour to see the city from the water.  You’ll learn a lot about the city and gain a whole new appreciation for the architecture in Chicago after the tour. Also, for a city that is known for the lake, river, and bridges, it would be a shame not to experience it first hand.  There are a few tours but I recommend Shoreline, I’ve always had great experiences with the guides which I’ve found can make or break the experience.

Once the tour has finished and you disembark at Navy Pier, take a bit of time to explore.  Yes, it’s very touristy, but you are a tourist after all! Navy Pier is home to the Centennial Ferris Wheel and it’s another chance to see Chicago from a different view.  After Navy Pier, you can continue walking the lakeshore on the Chicago Lakefront Trail for yet another view.  I would recommend walking south and then you can go to the Bean, Buckingham Fountain, and Grant Park.

I have a whole Chicago Brunch Guide if you are looking for other options.

Night

If time allows (which this should) I like to take some time to go back to the hotel and freshen up before dinner.  Tonight’s spot is Maple & Ash for some of the best food in the city. It’s a scene so take the opportunity to get changed, throw on some heels, and take a Lyft to dinner.  If you get there a little early, you can grab a spot at the bar and have a pre-dinner cocktail because those are delicious and it’s a great spot for people-watching.

You can call it a night, or have a nightcap back at your hotel.  A lot of Chicago hotels have rooftop bars so if you are lucky enough to be staying in one of those, do take advantage sometime during your trip. 

Related: My favorite travel beauty items and toiletries

Day Two | Enjoy the city like a local!

Day

After the jam-packed day yesterday, this morning starts with a laid-back brunch at The Hampton Social.  There are two locations for The Hampton Social but I recommend the Streeterville location for this itinerary since there is a rooftop and it’s closer to our next stop. Ask for a table on the rooftop but if you can’t get that then a table next to the windows will also give you some fresh air.  

After brunch, we are going to the beach!  I like to stop and get beverages and maybe some snacks (why does the sun make you so hungry?) and there is a Whole Foods on the way there.  It is about a 15 minutes walk from The Hampton Social to Ohio Street Beach. Whole Foods is a block east of The Hampton Social on your way there on Grand Ave.  Chicago has a lot of beaches on Lake Michigan but I’ve chosen Ohio Street due to its close proximity. Feel free to venture up north and go to the more populated Oak Street or North Avenue beaches.

If your hotel is anywhere near this location then I would take the time now to freshen up before dinner.  If it’s more north then you can freshen up after the next stop…

Night

The Zoo!!!  Chicago is awesome because it has a FREE zoo right in the city that is open 365 days a year.  Yes, Lincoln Park Zoo really is somewhere locals go. There are CTA buses that take you right there or you can rent a Divvy Bike if that’s something that interests you (I’ve never been particularly fond of riding a bike in the city).  The zoo closes at 6:30 on weekends so make sure to plan accordingly. But hey, it’s free so even seeing a little of it is totally worth it!

From Lincoln Park, walk the 20 minutes to Small Cheval on Wells St.  You can’t go wrong with anything here, but if you’d like to see my exact order check out my Best of Chicago guide.  Place your order and then grab a seat at the picnic-style tables.

After you’ve had your amaretto shake it’s a 10-minute walk to The Second City to get your laugh on.  Improv is one of the things Chicago is known for and there are different shows depending on what you are looking for.  If you have time before or after the show head to Utopian Tailgate which is a casual rooftop bar on top of The Second City.

Related: Unexpected travel essentials to take on your next trip

Related: What to do in Milwaukee ( a quick trip from Chicago)

Day Three | Becoming a fan

Day

Head over to Goddess and the Baker for breakfast this morning.  They have delicious coffee drinks and then you can choose something savory or something sweet to eat (or both!).  Today’s Chicago itinerary is classic day drinking. If you do choose to imbibe, I would definitely recommend using this to lay down a base.  

Hop on the CTA Red Line to Wrigley Field, home of the Chicago Cubs MLB team.  Public transportation can seem a bit daunting if you don’t know what to do, but I promise Chicago is an easy city to navigate.  For the full rundown check out my tips for How to Get Around Downtown Chicago. You’ll get off on the Addison stop for Wrigley Field.  There are probably going to be a lot of other people on the train in full-blown Cubs gear so follow their lead.

Wrigley Field and the surrounding area have been built up in recent years.  To get into the spirit (and spirits, haha) head to a bar and have some pre-game cocktails.  Depending on what you are looking for there are the classic dive bars like Murphy’s Bleachers or something more elevated like Mordecai.  Wrigleyville does have something for every kind of baseball fan.  

Night

Once the game is over there will be a lot, I do mean a lot of people leaving the stadium.  You can either start your walk to dinner now or wait until the crowd dies down at one of the bars or restaurants around the Field.

Dinner will be at Lou Malnati’s which is a 30 minute walk from Wrigley Field.  While they do have an exceptional thin crust here, can you really come to Chicago without trying the deep dish?  The answer is no, no you cannot. So do yourself a favor and try the deep dish with a butter crust. If you are craving some produce in your life after what has been a long, indulgent day, the Malnati Salad is so good.

Day drinking always makes me tired so I would call it an early night, knowing tomorrow is a travel day.

My Kind of Town, Chicago Is

I hope this has been a good starting point for your Chicago itinerary.   This is by no means exhaustive…if you live near an awesome beach, don’t spend your time in Chicago doing that, go to a museum instead. But if you live in a landlocked area, take advantage as not everyone thinks of Chicago as a beach city.  If you want a snack, hit up Garrett’s Popcorn or Molly’s Cupcake and you won’t be disappointed.  Oh, and check the weather and the sports schedule to see if you need to make any adjustments.  

Check out these other travel posts!

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

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