Planning the perfect travel itinerary can be quite daunting. What cities to visit, what activities are the best to do, how long should you spend in each location? There are always so many variables. This guide will teach you how to plan an itinerary for your next trip!

how to plan an itinerary

If you are like me, you love researching for your trip before you go. There is always so much to see and you don’t want to miss anything. Well, after traveling the world full-time for the last year, I have learned a lot about planning the best possible travel itineraries to get the most out of every trip you go on.

We’ll talk about how to research for a trip, where to find trip inspiration, what to search for trip recommendations, and more! 

These are the exact methods that I use to plan our itineraries for every single trip we go on. 

This post is all about how to plan an itinerary. 

How to Plan an Itinerary: 

Use our Itinerary Template

For the past few months, I have been using our Travel Itinerary Template in Notion to plan all of our travels.

>> Sign up for Notion for FREE! (not an affiliate link or sponsored post)

>> Download this FREE Notion Template to start planning your next trip!

This guide is best used with our template but can just as easily used with your own favorite method: on a piece of paper, in Google Docs, or even an iPhone note. I, personally, just love all the organization that Notion provides for my entire life!

1. Choose your Destination

Alicia smiling at camera in front of view over lake in Costa Rica

Honestly, there are a million destinations on my bucket list and I truly believe that I will get to all of them, eventually (positive affirmations, people!). So whenever it’s time to plan a new trip I usually just pick one and go.

Obviously, there is some decision-making process (budget, safety, COVID, etc.) but for this post, I am going to assume that we already have a destination in mind (city, state, or country). And we are ready to start making the itinerary!

For this example, we are going to plan a trip to Costa Rica.

2. Make an Itinerary Brain Dump

This is where we will start the actual planning process and this is one of my favorite steps. It gets me so excited to travel to the destination and just experience everything they have to offer!

This is a great place to start so you know what you have to work with and all the possible options in your country or city of choice.

Ever heard of a brain dump?

That’s okay, but I am here to show you the awesomeness of one.

A brain dump is a brainstorming session in which no filters are put in place. You write down everything you come across. These can be used in travel, clearing your mind, or coming up with date ideas, anything, really.

Sometimes you will get some really bad suggestions and that’s okay! It may inspire some really good ones down the line, so don’t dismiss anything in this first round.

What are we looking for?

When thinking of your end goal is to have a complete itinerary of cities to visit, activities to do, and more! Here are some examples of what we are looking for:

  • Cities/towns
  • Activities
  • Tours
  • Historic Spots
  • Instagramable Spots
  • Hotels
  • Restaurants

Again, this is just a brain dump so we are just gathering a ton of information so you can make better decisions in the end.

Where do put all this information?

All of my Itinerary Brain Dump information goes straight to the “Things to Do” section on my Notion Travel Itinerary.

>> Download this FREE Notion Template to start planning your next trip!

Each of the toggle bars is for a city or area of the country and within the toggle are things to see and do in that area.

Here is an example of what that looks like for my Costa Rica itinerary.

Screenshot of Things to Do for Costa Rica from The Passport Couple Travel Itinerary

Time to Search

Now that we know what we are looking for and how to organize it let’s jump into my three favorite ways to research itinerary planning.

Pinterest

Screenshot of Pinterest Search for "Costa Rica"

 

My go-to travel planning sidekick. I love searching Pinterest for all the wonderful travel inspiration. I have ongoing boards that I will pin to when I see something that catches my eye. But now that we are in planning mode, it’s time to load up on a ton of pins for one specific location.

Google

Screenshot of Google Search for "Best Cities to visit in Costa Rica"

After scouring Pinterest, I will jump on Google. This will usually bring up some top travel blogs for some great references.

Note: I skip over all the Online Travel Agency sites (Expedia, Viator, TripAdvisor) for now since they are likely just pushing the most booked things, which aren’t necessarily what we are looking for.

These articles should provide good recommendations for the main tourist cities and attractions.

Instagram

Instagram is great to search both locations and hashtags. I have found some beautiful waterfalls and cool street art that can be a bit harder to find in the larger cultivated blog posts.

This is especially helpful if you are looking for great Instagramable spots in your destination!

Note: Be sure to re-pin any articles that give you helpful information so you can reference again for more details or links and of course to give proper credit to the creator! And for Instagram give a like and save!

Search Ideas

  • Costa Rica
  • Costa Rica Bucket List
  • Best things to do in Costa Rica
  • Cities to visit in Costa Rica
  • 10 days in Costa Rica
  • Costa Rica Road Trip
  • Travel to Costa Rica
  • Costa Rica Travel Itinerary
  • Costa Rica Travel Guide

3. Get Specific

Girl at computer looking at The Passport Couple's Costa Rica Itinerary

Now that we have a huge list of things to do, we can narrow down exactly what we want and can do. This is where the itinerary gets a little more shape and starts to feel real!

Look at Activities

The first thing we want to do is figure what is the main city or cities we want to visit. I will open all the toggles on the template and look at what has the most listed beneath each one.

Of those, I will look at what I most want to do. Do I want a beach vacation, a hiking adventure, old city vibes, etc.?

How to Get Around

Next, you will want to ensure you have the right method of transportation to get around. There is a lot to consider here: how to get from the airport to your first city, how to get around in each city to all the sights, and how to get between cities.

Some awesome places you want to visit may be really hard to get to. Some cities may be extremely walkable and just what you are looking for. And others may not have any roads and you have to walk everywhere and that’s not what you are looking for.

This has definitely been a major factor in our planning process and some trips call for road trips others call for public transportation and walking.

Budget Comparison

Every trip should have a budget, whether line-by-line-specific or an overall goal. This is the time to make sure your accommodations and activities in each location match your budget.

We have found places that have tons of free activities and walking tours, while others are all tours and adventure activities that cost quite a bit of money. The same is true with accommodations. The Amalfi Coast, Italy is very different than Halong Bay, Vietnam.

4. Plan the Perfect Itinerary

Girl typing at computer

Once you have your cities chosen, you can really get specific on the plans for each location.

Activities

I usually go back through and get really specific with my searches. If I know I am going to stay in San Jose, Costa Rica after the last step and one of the recommended activities is to visit a waterfall, I want to make sure I visit the best waterfall. You can just follow the same steps from earlier with Pinterest, Google, and Instagram!

More Search Ideas

  • San Jose, Costa Rica
  • Things to do San Jose, Costa Rica
  • San Jose, Costa Rica Bucket List
  • Best Activities in San Jose, Costa Rica
  • San Jose, Costa Rica Travel Guide
  • 3 Days in San Jose, Costa Rica
  • Day Trip from San Jose, Costa Rica
  • Best Beaches near San Jose, Costa Rica
  • Top Restaurants in San Jose, Costa Rica
  • Best Waterfalls near San Jose, Costa Rica
  • Coffee Tours in San Jose, Costa Rica

Google Maps

Google Maps screenshot for Costa Rica

Google Maps has become such a useful tool in my itinerary planning. I will pin everything I know we want to do to a new list in Google Maps. This way I can see where everything is located to each other.

This helps a load to finalize the plans! It will help you find a good location for your hotel, first of all. And this will allow you to see if you can do multiple things on the same day.

Itinerary Time

Screenshot of Itinerary for Costa Rica in The Passport Couple's Travel Itinerary Template

Finally, now you can put everything on the table! There’s no magic button but just a lot of maneuvering all the activities around.

This is where you’ll be able to see how many days you can spend in each city and what exactly you’ll have time for!

I start from the day we land and depending on the time of day we land and get to the hotel, will usually schedule a chill, exploring day the next day. Not a sunrise hike for 3 am. From there I will put the most important stuff on the table first and add in the smaller activities if there is time.

I also add in specific meals on certain days if I know we’ll be in the area or maybe a handful of restaurants so we can choose on the day.

But there is no perfect method as everyone wants to plan their trips differently! So this is up to you 🙂

Extra Tips

Here are just a few more tips to ensure you get the perfect travel itinerary!

  • Include Chill Days: Every time I forget to schedule a relaxing day, we end up taking one anyways and then don’t get to do what we planned that day AND we feel guilty about it! Remember you are traveling and exploring the world, don’t make room for guilt or pressure to do everything! We usually plan a day by the beach or the pool or even schedule a movie night at a local theater (pre-COVID, obviously). These help us feel saner when we have a jam-packed schedule of exploring!
  • Don’t Forget Sunrise & Sunset: These are always some of our best memories while traveling. The magic of sunrise and sunset is just remarkable. I always do my research to find the best sunrise and sunset spots and it really makes such a difference.
  • Know What Food to Try: One of my favorite things to do is eat while traveling. I am sure you may feel the same, so now is a good time to also search for certain meals or foods to try while visiting. Sometimes it will be restaurant-specific but often it will be a meal that you just have to order somewhere. Our favorites are always the local, traditional dishes!
  • Itineraries are Not Steadfast: And last, but certainly not least, is that your itinerary is never set in stone and THAT’S OKAY. This itinerary is just to get you more prepared for your travels and not be a step-by-step plan for your trip. Some of the most exciting things happen spontaneously. And if you don’t get to do everything on your itinerary THAT’S OKAY. We actually have never done every single thing on our list. We use it as more of a guide and if we have time I would rather have options to choose from than not have a clue what we’re doing.

Now go plan away and enjoy your trip! 

This post was all about how to plan an itinerary. 

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