How to Plan a Vacation (with timeline)

If you are here that means you thinking of going on vacation, yay!!! That’s one of my favorite things to do, and for me, part of the fun is actually planning the trip. You’ve decided where you are vacationing, when you are going, and your travel budget, but now what? Below is the ultimate step by step guide on how to plan a vacation.

If you read to the bottom you can sign up to get a free downloadable travel planning timeline, just pop in the date of your vacation and it will tell you when you need to complete all the below steps. Happy planning!

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.

Table of Contents

Apply For Global Entry

In the US the Customs and Border Protection offers a program that allows low-risk travelers to apply for expedited customs clearance. You’ll need to pay the fee, apply, and then go in for an interview. It’s a completely optional thing to do but it can save a lot of time going through customs. If you don’t already have TSA Pre-check (which allows for an easier time going through security), this is a no-brainer because you’ll get both with the Global Entry approval.

If you think you will travel internationally more than once in five years (which is how long Global Entry is good for) you may want to check this out. Anything that can take the hassle out of traveling is worth it to me. Plus, when it’s been a 10+ hour travel day, don’t you just want to get home already?

Book Airfare

The timing of when to book International airfare and Domestic airfare is a little different. International you’ll probably want to book further out and Domestic you have a little more time with. Also, if you are planning on using points then you’ll most likely want to start your search earlier as airlines only allot a certain number of redeemable seats.

I like using apps like Kayak that recommend if you should buy now or wait, and you can also set up alerts for price changes.

Related: An Honest Review of the Excellence Playa Mujeres Resort Near Cancun, Mexico

Book Rental Car

If you will be driving in your destination then you’ll probably need to book a rental car. My recommendation is to do it sooner rather than later but check the cancellation policy. Usually, there is a flexible policy so you can lock the rate in at what you feel comfortable with, but if it goes down you can cancel and rebook.

In the U.S. I’ve found that if I book a car through Costco Travel it’s the same price as elsewhere, but for an upgraded model.

Note if you are driving internationally you’ll get a better rate if you book a standard transmission over an automatic, but make sure that you feel comfortable on all types of terrain (the hills are alive with the sound of music, you know).

Related: International Travel Tips for Beginners

Book Train Tickets

If I’m taking a relatively short train ride (a couple of hours) I tend to purchase the ticket right before I get on the train. That way I have more flexibility on the day of departure and I’m not a prisoner to the schedule. Let’s say I decide I want to have brunch in my departure city then I’ll leave later. If I’m eager to get to my new destination, then I may want to take the first train out.

However, like most things, if there is a limited supply and I’m dead set on what I want to take then I book it in advance. Let’s say I’m planning to take an overnight train from Florence to Munich, I’m going to want to make sure I book that in advance (I’ve had to share a sleeper car with strangers before and it is not ideal).

Apply For Passport

Most people know that if you are traveling internationally then you’ll need a passport. But what some may not realize is that even if you have a passport, but it expires within six months of your trip, you’ll need to renew it prior to leaving.

Apply For Visa

To visit some international destinations you may need a travel visa, depending on your length of stay. I’ve used this company in the past and they have a tool for you to check your destination requirements.

Schedule Travel Vaccinations

Just like a travel visa, vaccination requirements are dependent on your destination. It may also be required or recommended that you start on preventative medication before you leave the U.S. The U.S Department of Health & Human Services is a great resource to make sure you are up to speed on all requirements.

Research this early because you never know how long it will take to get an appointment at a vaccine clinic or your doctor. If you need a vaccine administered 4-6 weeks in advance, you may need to call much earlier to secure the appointment.

Book Hotels

I’ve learned this lesson the hard way but I highly recommend booking a refundable rate. It may cost a little more in the short term, but if something happens you won’t lose your money and you’ll save in the long run. If the room rate decreases after you book then you can cancel (according to the refundable rate policy) and rebook at a lower price.

If you are flexible with where you stay and aren’t a big planner, you may be able to get a great last-minute deal. I, for one, would be anxious about planning a trip in advance and not having a room booked. But if that’s not you, then booking the hotel the day prior to your vacation or the day of may result in a great rate since guests may have taken advantage of the 24-48 hour cancelation policy.

Redeeming points may take a little bit more research (what method takes the lowest amount of points, transferring points, etc.) so I recommend booking this as soon as the rooms are released. Also, just like airlines, there will be a limited amount of rooms in each tier that are redeemable so do that as soon as you can.

Related: Unexpected Travel Essentials

Make Dining Reservations

If you have your heart set on dining at a specific spot, especially if it’s a popular destination, this will take a little more research.

A lot of restaurants open up reservations 30 days in advance so you can book it then, but somewhere like Disney World is 60 days in advance and you won’t want to wait until that 30 days or you will miss out. One of my favorite places in my city only opens up reservations 3 days in advance so I set my alarm that morning to book.

I recommend researching well in advance, around 3 months out. Then make a list of the places you’d like to dine at, find out when their reservations open up, and add that date to your calendar. It may seem like a lot of work, but it will be worth it. Especially if it’s a destination you aren’t certain you’ll revisit.

Get an International Driving Permit

Some countries require an international driving permit, IDP, so if you are planning on driving a car you’ll want to see if your destination does. An IDP is an official translation of your US Drivers License, so you’ll need that first and foremost. I’ve gone to AAA and applied, it’s relatively inexpensive and you don’t need to be a member.

Depending on who you talk to an IDP may or may not be totally necessary. I tend to err on the side of caution when following international laws, the last thing I need is a Brokedown Palace situation (I mean that’s an extreme example, but you get the point).

Shop for Specific Clothes and/or Gear

After what can seem like forever planning a vacation, inevitably the date quickly approaches, and then I’m like, ‘oh wait, I wanted to get a new bathing suit, raincoat, etc.’ So don’t do this and wait until the last minute and then buy something you don’t really like only because that’s what time you allowed.

Make a list of things you don’t have in your closet that you want for your trip and then start researching. Give yourself plenty of time to research, order, and have it shipped.

Related: The Best Travel Sized Toiletries and Make-up Items

Shop for Toiletries

Since I’m a consistent traveler I like to keep my toiletry bag stocked at all times. And if I run out of something on my trip, when I get back I order a new one so my bag is ready to go for my next vacation. However, if you don’t travel that often then take stock of what travel-sized items you have already, and what you need. Just like shipping for clothes, you want to give yourself enough time to buy the good stuff and not just run to the drugstore because it’s the night before and you realize you don’t have a travel-sized dry shampoo (of course not speaking from personal experience).

Also, I read something years ago and it shifted my way of thinking about packing toiletries. Even if you are checking a bag and can bring your full-size bottles doesn’t mean you should. Do you really want to take up precious space carrying around something you know there is no way you’ll ever use? Think about how much space, for no reason, a full-size shampoo, conditioner, and lotion bottle would take up. If you buy these containers and transfer those three things could take up less space than one full-size bottle. And a lot of brands offer travel sizes you can buy too…but only if you give yourself the time to buy them.

Apps for Vacation Planning

I’m known to book a vacation entirely on my phone. Here are my favorite apps for vacation planning.

Kayak | I like to use this to search for flights since it advises you when to buy and you can set an alert, but you can also look for rental cars and hotels
Skyscanner | Another app I use to search for flights when I’m flexible, a cool feature is it will show you prices for different date ranges
Booking.com | If I’m not looking to redeem or earn points I start my hotel search here to see everything that is available
Hotel Tonight | This is the place to go to find a last-minute hotel deal, the day I wrote the post a 5-star hotel in Chicago was $700 off the regular price. It’s a great staycation App
VRBO | I’m not usually a rental home kind of person, but if that’s the route I’m taking I like VRBO filtering options
Tripadvisor | A great place to see reviews and for hotels but also a place to review and book excursions
OOO | A recent addition to my travel app vacation planning, you can follow people and see what they recommend. I only just started adding recommendations, but if you download it make sure to follow me @ VeryObsessed

Map for Vacation Planning

As an elder Millennial (sure we’ll go with that), I remember the days when we traveled with paper maps, but I don’t miss them. I love not having to carry bulky things when I travel so having a map on my phone is ideal. However, there are those times when you don’t want to use data, or you don’t have a new SIM card yet, or the service is just awful. So for those times, how do we plan ahead? Google Maps is the answer.

There are two different ways to use Google Maps for vacation planning.

Use it only as a map | To have a map at all times open the Google Maps app on your phone, search your destination city, and click download. Now that map will be on your phone for a year and will be available, even if you are offline.
Use it for specific destinations | If you want a map that details points of interest then open the Google Maps app on your phone, search for a specific place, click save, create a new list, and name the list. Keep adding spots to the list and then when you are looking at the map (which you can download) you’ll see where those spots are and when you are near one.

Take the Stress Out of Planning Your Trip! Download the Free Vacation Timeline Planner Today.

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.

Pin post to save for later: