How to Build a Travel Itinerary of Memorable Activities for YOU

So. You saw a breathtaking photo of CITY-OF-CHOICE on Instagram and you’re ready to book a flight and take the whole fam.

Now what?

This is one of the most common questions I get about travel — how do you find things to do? So here it is, a snapshot of the travel homework I do before every trip, whether it’s a quick weekend or a week-long adventure.

First, Search + Gather

This is the first step, and is where the heavy lifting is done. This is the phase during which you scour the internet and gather all the fabulousness in one place so you can sort through it later. Everybody immediately thinks of Pinterest (which is usually the best place to start!) but don’t forget these sources, too:

  • Travel blogs.
    Use search terms like “Unique Activities for Kids in DESTINATION-CITY” or “DESTINATION-CITY Hidden Gems” or “Top 10 Things to Do in DESTINATION-CITY”. The internet is full of stuff like this. And it’s a great starting point. Also search for specific things your family likes. At our house, we’re into history and science and active experiences. So I search for “DESTINATION-CITY Science Museums” or “Historical Landmarks in DESTINATION-CITY”. If you’re into art or photography or sports or great restaurants or unique hotels or live music — use those interests when you search and you’re one step closer to planning a trip for YOUR family.
  • TripAdvisor.
    My favorite place to read reviews! TripAdvisor is great at linking activities together at a given location. If you’re reading reviews about Activity A at your destination, TripAdvisor will suggest Activities B, C, and D that are geographically close or things that people typically do together on one trip. (TripAdvisor can also be a great place to compare vendors and companies for a popular activity. If you’re going to the beach and want to take a chartered snorkel trip — you will likely have tons of options. Use TripAdvisor to read reviews and see photos and get real opinions of people who’ve used those vendors and you’ll feel much better about booking an excursion.)
  • Tourism Boards and Chamber of Commerce websites.
    I like to know what’s unique about a place. Often, if a city has a unique claim to fame — this is where you’ll find it. While planning a recent trip to Hutchinson, Kansas to visit a space museum we discovered Hutchinson is also the hometown of another unique destination — a live salt mine open to tours. We only found it when we started poking around about a town we’d never been to — we might have otherwise missed it!
  • Check the Calendar.
    Find out if there are local festivals or holidays you can experience when you’re in town. Or… you may want to plan AROUND these things if the crowds aren’t your scene.
  • Ask Around.
    I notice people using the Facebook recommendations tool ALL. THE. TIME. Keep in mind you’ll get advice from all corners if you do this — so be ready to get fancy restaurant recos from your newlywed couple friends mixed in with suggestions for the best parks and museums for kids. You’ll really need to process through what works for your family and your traveling style (but Spoiler Alert! We’re going to do that anyway in a minute.)

As you start the Search + Gather Phase, open a document on your computer or phone and use it as a dumping ground. Make lists, notes, copy/paste links — just get it into one place. Restaurants, tours, hotels, parks, festivals — all of it. Just capture it. We’ll make sense of it later. {Quick note: I do use Pinterest boards for initially gathering links and articles, but I prefer having a document so I can turn it into a usable itinerary during my trip.}

Then, Prioritize + Filter {You can’t do it ALL.}

Ok, so now you have a jumble of links and ideas and photos — time to sort it out. I apply a few different filters at this stage — so that my family is taking the trip that is just right for US.

  • Filter by Season
    First, consider what time of year you’ll be traveling and get rid of ideas that won’t be available during that season. I went to Iceland last summer, and while “See the Northern Lights” is on every Top 10 Iceland list on the entire internet — you can’t see the Northern Lights in the summer, so it dropped off the list. One of these days I’m going to plan an entire weekend in Washington DC around enjoying the cherry blossoms — but so far, I’ve only been in the summer and fall — so no cherry blossoms.
  • Filter by Priority
    Next, identify the top things you consider your deal-breakers. Your must-dos. These will be something you plan around and need to come first on any itinerary. If there’s a National Park nearby and you know you will want to spend an entire day there — earmark it. If you’re going somewhere famous for incredible sunsets and you want to enjoy them every night — put it on the itinerary and know that whatever else you’re doing during the day needs to wind down in time for you to be staring at the horizon by then. Don’t let other things squeeze out your top priorities.
  • Filter by Day
    In researching travel activities I’ve come across plenty of things that only happen on certain days of the week — and sometimes I learned that in time to plan ahead, and sometimes I didn’t. We’re planning a trip for Spring Break this year and one of our activities is a tour that is only offered on Wednesdays. Since most anything else can be done any day of the week, I started our itinerary by putting that tour in the middle of the week — instead of trying to move things around later.
  • Filter by Geography
    Depending on the location, you could be spending time in the car or public transportation going place to place or city to city across a state or country. Make a plan to minimize this! If you’re going to NYC, don’t plan to see the Statue of Liberty and Coney Island on the same day — they are potentially hours of car/train travel apart! Group things on your itinerary using a map so you efficiently move from one place to the next instead of criss-crossing a city or having to double back for something you missed.
  • Filter by YOU
    This may be my #1 piece of advice when planning travel. Do what makes sense for YOU. If you use all these search terms and filters and forget to ask yourself what YOUR family thinks is fun — you’re missing it! I mentioned science and history and active experiences are targets for our family — if these aren’t your thing then cross the museums and day hikes off your list in favor of what your people will still be talking about for months and years to come. In our family, food rarely makes the list of destinations. We aren’t foodies and we don’t have much patience for waiting. I almost never capture ideas for best restaurants in an area because we are just as happy with a food truck on the go or room service when we’re done for the night. Do what works for YOU.

According to a study published in the journal Applied Research in Quality of Life, just planning or anticipating your trip can make you happier than actually taking it. While I CERTAINLY don’t recommend planning a trip… and never taking it — I do believe the planning phase can be a lot of fun. It can reveal pockets of interest in your family just waiting to become adventures. Happy planning!

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