How to Plan An Unforgettable Trip Around Essential Travel Experiences + Free Printable Planning Template

Once you’ve picked your destination, it’s time to start building an itinerary for an unforgettable trip. Though it’s great to leave your schedule somewhat open and flexible, I find it’s a good idea to plan around a few ‘must have experiences’ to give the trip a little structure and ensure we’re not missing out on key activities!

While I love planning our vacations, starting with a blank itinerary can be a little overwhelming and stressful!  Many guidebooks and blogs provide example itineraries and ‘top things to do list’, but I don’t recommend following those to a ‘t’. While those can be great for inspiration, they are rarely perfectly aligned to your dream vacation. Sometimes, those ‘top things to do’ lists are full of busy tourist traps that every other traveler is going to visit as well. I also often find that they those canned itineraries are far too busy and keep you constantly running.

Likewise ‘top attractions’ list can start to feel like you’re simply checking off experiences to say you did it. So, we’ve started planning around few ‘Must Have Experiences’ that we absolutely want to have on our trip and leave the rest of our time open for unstructured exploration and relaxation.

TIP: This process is incredibly helpful if you’re traveling as part of a large group or with a new travel companion. Create this Must Have Experiences list together to make sure that everyone gets to contribute to the travel plan and ensure expectations for the trip are at least somewhat aligned.

To help you to plan your Must Have Experiences, we’ve created this printable template and the following guide to start your planning!

Step 1: Brainstorm ideas

Start listing out the experiences you want to have. I try to leave this list as generic as possible to avoid boxing ourselves into a specific sight or activity at this point. Sometimes Mike and I will generate this list together over the course of a week or two once we decided on our destination.

  • Why did I pick this destination?
  • What experiences do I want to have before I come home?
  • Is there an experience I’ve always dreamed of having?
    • Food I’ve always wanted to try?
    • Sight I’ve always wanted to see?
    • Activity I’ve wanted to try?
  • What is the destination known for?
  • Are there any experiences that are ‘limited term’? Like a festival, event, or special attraction that won’t be there for long?

This is also where broad research on your destination can come in handy. I like to use guidebooks and blogs to get general advice on what I should do, without locking anything in quite yet. We’ve also suggested examples of our ‘Must Have Experiences’ in our Destination Guides, so feel free to use those as a jumping off point!

Need more inspiration? Read Best Places to Travel in 2020 List Roundup

Step 2: Whittle it down to your ‘Must Have Experience’ list.

I try to keep our ‘must do’ list down to only a handful of experiences we want to build our trip around. A good rule of thumb has been to plan no more than 1 ‘must have experience’ for every day of the trip. So, if we’re going for a week, we might plan for maybe just 5-6 ‘Must Have Experiences’.  Don’t worry if that seems like it’s not enough. You’ll be able to fill it in later.

Also, don’t worry about making this too specific yet. Some examples of ‘Must Do’s’ from one of our trips to London included:

  • Go to High Tea
  • See a professional soccer match
  • Visit historic pubs
  • See a show in the West End
Step 3: Start researching specific activities/ sights that relate to your ‘Must Have Experiences’

While sometimes a ‘Must Have Experience’ is a specific activity that you know you want to include, like go on the London Eye, often you will need to do some additional research to find the exact activity that will give you the experience you want to have.

Now’s the time to start more in-depth research! Be sure to capture location, opening times, costs, and other important information that will help you structure an itinerary later on. It’s best to have a few options to choose from, if possible. For example, if our ‘Must Have Experience’ is to Take a Food Tour, I will look up options from multiple tour companies to find the ones that we like and fit into our itinerary the best.

Step 4: Build Your Itinerary

Once you’ve narrowed down your options for Must Have Experiences, start to play around with how they will fit into your itinerary. Sometimes everything fits beautifully, other times, you will have to make hard decisions to pass on experiences for this trip.

For example, on a recent trip to Paris, Mike and I put ‘Sancerre Wine Tasting Tour’ pretty high on our Must Have Experiences List. However, once we started researching options, we came to the realization that our schedule would be too full and we’d feel rushed. We ended up skipping the countryside and stayed in the city, opting to have a picnic on the banks of the Seine- complete with wine from Sancerre. 😊

Download the FREE PlanIt Wandering Must Have Vacation Experiences Printable Template

Need more help on how to build your itinerary?

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