6 Easy Steps to Planning an Itinerary You’ll Love for Your Next Trip

When it comes to creating your dream trip, planning an itinerary is an essential piece to keeping things organized and running smoothly. If you’re going to visit multiple destinations, putting all the pieces together in one place makes sure all your dates line up and you don’t miss anything. Having a process to follow while planning will also help you save time when you’re researching the different elements of your travels. In this post, we’re going to talk about the steps to follow when planning an itinerary so you can feel totally prepared and organized for your next adventure. Let’s go!

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It All Begins with Time & Money

Before you start mapping out your itinerary, it’s important to know how much time and money you have to spend. These are the parameters everything else has to fit within. Getting clear on these pieces up front makes the whole process of planning an itinerary much easier. 

Having a clear timeline for your trip will help you decide everything from where you’ll go to how you’ll get around. Be sure to consider the travel time involved in getting to your destination and home again. Knowing how much time you have will also help you plan your travel budget since that money will have to cover the entirety of your trip. 

Your travel budget may be another factor in where you choose to go and how you spend your time there. It will need to include all your accommodations, activities, food, etc. There are a couple different ways to decide and plan your travel budget. You can find out more about how to calculate the amount you’ll need and what it should cover in this post.

Planning an Itinerary Step 1: Choose Your Destinations

Before you can take the next step in planning an itinerary, you have to know where you’re going! I swear, this is one of the hardest parts of creating your next adventure -- taking a world of possibilities and choosing only a few places to see in a single trip. It’s important to narrow your list down to a top three that you’ll look into as you go through the rest of the process of planning an itinerary. 

When you’re thinking about which destinations you’d most like to visit, take some time to think about what’s most important to you for this trip. Do you want to rest and relax, with big parts of your day set aside for downtime? Do you want to go exploring, spending your days discovering what’s hiding around the next corner? There’s no right answer, but knowing what kind of experience you want to help will help you make other decisions later in the process. Understanding what type of traveler you are will help you figure out the kinds of places that feel awesome and how you want to spend your days. Check out this post with more tips for choosing a destination you’ll love.

Planning an Itinerary Step 2: Outline Your Time

Now that you know your travel budget, how much time you have to spend, and where you want to go, it’s time to see what this can really look like. The next step in planning an itinerary is to outline possible timelines for your trip that include the places you want to go and how much time you’ll spend in each. You can configure this in a number of ways, so follow the steps below to make it easy!

First, decide what you absolutely must see in each of your top three destinations and make a list. Next, list how much time you’ll need for each one. I recommend only planning one or two per day. The truth is, unless you have months to spend, you’re never going to see all of the things in all of the places. I know, it sucks, but that’s one of the hard parts of travel -- making peace leaving some things unseen. You might get to all the things on your list but I promise, you’ll find more that you want to do once you get there. Decide what’s absolutely essential and if you have time for more, great! Start outlining your timeline with these items and build from there. 

Once you have your list of essential sights and activities, think about the overall pace of travel. Do you want to spend your days running from one thing to the next? Do you want some downtime for wandering aimlessly or spending a leisurely afternoon in a café watching the world go by? This is why one or two big activities in a day is plenty! Some of the most magical travel moments happen outside what you actually planned. Leave some room for the good stuff you find along the way. 

Planning an Itinerary Step 3: Map Potential Routes

This is where it gets super fun! Well, for me at least since I’m a nerd for maps. Now you get to spend some time creating different route options for your trip. Are two of your top destinations close enough together that you can do both with a train ride or road trip? What else is around your destinations that you might like to see. Now that you have an idea of how you’d like to spend your time, get creative with how you’d like to fill in the gaps. Here’s a post about different ways to get around on your trip that will be helpful while you’re mapping out potential routes. 

Google Maps is my go to for this part of planning an itinerary. You can create your own maps that let you customize the stops and connect them so you can see what it would look like. The driving directions help you get a good idea of the travel time from point to point and you can also look at train routes as well. Personally, I love to play with different places and routes until I’ve created the perfect travel itinerary. 

There are a few different ways to consider when creating a route for your trip. You can fly into one destination and home from another. Staying in one place and taking day trips is another great option. And road trips are one of my favorite ways to see a place, whether you start and end in the same city or drive from one to the other. There are a variety of options for transportation when you’re planning an itinerary so mix and match in whatever ways work best for your time and budget. 

Planning an Itinerary Step 4: Let Budget Be Your Guide

Now that you’ve given yourself options, it’s time to make more solid plans. Start with the route you’re most excited about and do a bit of research on flights and accommodations. Work through your routes one at a time, making note of which pieces work and which don’t quite fit your needs. As you do the research, keep track of the dates, flight routes, and travel times so you’ll be able to easily compare them when you’re finished. 

First, research flights. This piece has the biggest variance from day to day and week to week so planning an itinerary around affordable flights is the way to go! Skyscanner.com is my go to for finding the best flight options for my time and money. You can search for a whole month at a time, look at the cheapest places to get from a specific location, and even set alerts for routes so you’ll know if prices drop. To get you started with your research, here are a handful of tips for finding cheap flights that work no matter where you want to go. 

Once you’ve found a few flight options that will work for your time and budget, have a look at accommodations. Booking.com is my favorite for this because it shows all the different options and price ranges in one place. This is an element where you can save a ton of money in your travel budget, if you know what to look for! Here’s a post about the different types of accommodations and how to choose the best one for your budget and experience. 

The last thing to do, for now, is research how you’ll get from place to place, if your itinerary will have multiple stops. The timetables and prices don’t change much on transportation and you won’t be able to book many of them more than 90 days in advance. This research is just to make sure you can get from one destination to the other easily and affordably. 

Planning an Itinerary Step 5: Book the Essentials

Once you’ve found flights that fit your needs and confirmed there are accommodations that work for you, it’s time to book! Organize the research you’ve done in order of dates to make sure it all lines up the way you want. Start by booking flights -- I always book directly through the airline instead of through Skyscanner (or another flight search engine) to make sure I can get help directly from the airline, if I need it. 

Once you’ve got your flights booked, move on to accommodations. Make sure to look at any date changes with your flights, if you’re crossing oceans. One of the other nice things about Booking.com is that many of the accommodations don’t require any payment up front and are refundable. Book the ones you want and keep track of how much you’ll need to pay and when. This will help you keep your travel budget on track! 

Set a reminder in your phone for about three months before you leave so you can book any transportation or activities you need to. Be sure to look at the Go City passes as they can save on entrances to attractions and, many times, include access to public transportation. This is also a good time to look at any of the major attractions to see if you can (or need to) pre-book, which can save you time getting in, once you’re there. This will make sure you don’t miss anything on your “must see” list, like the Anne Frank House in Amsterdam I had to skip because I didn’t book far enough in advance. 

Planning an Itinerary Step 6: Take it With You

As you start booking, create a document that has all the important information for your trip. For flights, I include which airline, flight numbers, routes, layover times, and confirmation numbers. When booking accommodations, note the dates, name of the place, the address, phone number, and confirmation. Depending on the transportation, you may need to print physical tickets or simply download an app. All the instructions should be provided when you book. 

Once everything is reserved, your itinerary should fit on two pages that can be printed front and back. Print a copy of this to take with you so you have everything at your fingertips when you need it. You can also download it to your phone as a PDF so you can access it that way. For safety, it’s a good idea to share it with a loved one or two at home so they know where you’re supposed to be and when. I always give my mom a copy of the itinerary and Stan too, if he’s not adventuring with me on a particular trip. 

That’s it! You’ve spent the time planning an itinerary and organizing it in a way that will make it super easy as you go along. Now it’s time to go and enjoy this amazing experience you’ve created for yourself! 

Your Turn

How have you planned an itinerary in the past? Share any of your tips in the comments!