How to Plan Your Best Possible Family Vacation Itinerary
How to Create the Perfect Travel Itinerary for Your Family
Planning an itinerary for your family vacation can be incredibly fun and exciting, but it can also be frustrating and tricky.
For me, doing the research and reading about what other people have done gets me excited to visit the area and increases the anticipation of the trip. For others, it can feel like hell to sift through countless blog posts, Youtube videos, Instagram photos, guidebooks, and articles to find activities your family won’t complain about.
Regardless of how you view itinerary research and planning, it’s something that has to be done, unless you plan to spend literally your entire vacation at an all-inclusive or laying on the beach. (No judgment! Sometimes that’s exactly what you need).
I plan multiple trips per year for our family. Some are quick weekend trips where we’re trying to cram everything interesting in a day-and-a-half, while others are week-long travels that require much more meticulous planning.
Here are the top resources and tips I use to get the most out of my research while planning for a trip to make it more exciting and less frustrating.
Happy travels!
Disclaimer: This post contains affiliate links, which means if you click a link and make a purchase I may receive a small commission at no extra cost to you.
VACATION PLANNING SERIES
This post is STEP 5 in my vacation planning series for families. I’ll link the rest of the posts here as they are complete, so you have a step-by-step guide for planning the best possible family vacation.
In my experience, moms are often the ones doing the behind-the-scenes research, planning, calling, booking, list-making, grocery shopping, and packing, and it can take all the fun out of travel for her while the rest of the family sits back and enjoys.
This series is designed to streamline the process for busy moms who don’t have time to figure it all out on their own. I’ve also created a Family Travel Planner that will help organize your research and trip details so that you don’t constantly feel like you’re forgetting something.
STEP 1: How to Budget and Save for Your Dream Vacation
STEP 2: How to Choose the Perfect Destination for Your Family Vacation
STEP 3: Tips for Finding Affordable Flights for Traveling Families
STEP 4: How the Find the Perfect Accommodations on Your Next Trip
STEP 5: Tips for Planning your Family Travel Itinerary
DOING YOUR INITIAL RESEARCH
In my opinion, initial research is easily one of the most enjoyable parts of travel. You can let yourself be inspired by others who have completed similar trips. There’s no pressure to get bogged down in details or budgets. You let your imagination run while and can truly savor the anticipation of your trip as you discover all the cool things you can see and do there.
Both fortunately and unfortunately we live in an era of almost unlimited access to information. This is amazing because you no longer have to go out and buy a guidebook to find information about your trip. This can also be overwhelming because if you’re visiting a popular destination you might be so inundated with suggestions you don’t know where to start!
I’ll share with you my process of planning an itinerary start to finish.
Full disclosure: I’m very organized, but I’m also pretty Type B, meaning I don’t like to have everything planned down to the second. You can always tweak my suggestions to make them work for you and your family!
MAKE A LIST
First, you’ll need somewhere to jot down ideas and suggestions. Maybe you like a good old fashioned notebook and pen. Maybe you use a bullet journal. Maybe you want to use a Google Doc you share with your spouse.
Regardless of HOW you make the list, you’ll need somewhere to write everything down that catches your eye in the initial research phase.
Don’t forget, my Family Travel Planner has a page dedicated to this, along with thoughtful questions to consider as you plan your itinerary.
START WITH PINTEREST
My personal favorite first stop in the itinerary planning process is Pinterest.
Remember, Pinterest is not a social media platform. It’s a search engine. So use it that way! I personally prefer doing initial research on Pinterest rather than Google because the articles tend to be written by travel bloggers or people who actually went on vacation in the destination I’m planning to visit, while Google searches tend to yield larger websites with more generic top 10 lists (which always end up being the most obvious 10 things to do there).
In articles you find on Pinterest, you won’t just find the famous landmarks, experiences, and attractions, but personal recommendations for restaurants, Instagrammable spots, streets to wander, directions, and helpful tips.
DO A GOOGLE SEARCH
Next, I’ll do a quick Google search and read through a few articles to see if there was anything obvious that I missed in my Pinterest research. I’ll often go to pages 2, 3, or 4 in the Google results to bypass the bigger websites.
You also might want to take time in your Google search to read through sites like TripAdvisor where you’ll find tons of online reviews. I don’t put a lot of stock in negative reviews, but if there are many that are all saying similar things, I’ll definitely take that into account.
SCROLL INSTAGRAM
Did you know you can save photos on Instagram and even create folders to organize them? You can use this feature to help find fun or interesting spots that might not pop up on your other searches.
For example, let’s say I’m planning a trip to New York City. I’ll start by searching “visit New York City".’ "(You can do this with whatever city, state, or country you’re visiting: “visit Fort Myers Sanibel” “visit San Antonio” “visit Paris” etc etc).
Usually, the first website to pop up is the official tourism board website. Look for their social media links to find them on Instagram. For New York City, that would be @nycgo. In the description of their Instagram page, they will usually have a hashtag you can use to tag photos from your visit. Check out that hashtag for lots of ideas, then save them (the bookmark icon in the bottom right corner of the photo) to your folder!
I usually use this tactic to find cool-looking desserts, beautiful photo spots, and cute coffee shops.
SEARCH YOUTUBE
If I decide to check YouTube, it’s because I’ve been reading up on a destination but I can’t quite picture it in my mind’s eye. I don’t necessarily go to YouTube for NEW ideas, but to get a better idea of the layout of a place.
ASK AROUND
Don’t forget to check your IRL network of friends and family to find tips about a destination. Put a call out on Facebook or plan a coffee date with a friend who has visited in the past.
Usually, they’ll be able to give you a pretty honest review of what a place was actually like and whether or not it was worthwhile. You’ll also be able to ask them inside tips like how far in advance they booked, how long they had to wait in line, where they ate, etc.
READ A GUIDEBOOK
As a millennial (even a millennial who loves to read), looking up information in a physical guidebook doesn’t always occur to me right away.
Guidebooks tend to go way more in-depth than a blog post ever could on a topic. It definitely doesn’t hurt to supplement your internet research with a guidebook to make sure all the logistics are covered. Just make sure the book you choose is fairly up-to-date. The library carries many of these, or you can find them on Amazon!
VISIT THE OFFICIAL TOURISM WEBSITE
Many tourism boards use their website to provide free itinerary suggestions for different types of travelers. Categories might include an outdoor adventure itinerary, a family-friendly itinerary, and itineraries for couples, solo travelers, and people traveling with pets.
You’ll also find tips for what to do there during different seasons, lists of free things to do, ideas for first-timers, etc. Basically, they’ve got you covered no matter what you hope to get out of your trip. They often provide free resources and maps, too!
DON’T DISCOUNT PHOTO SPOTS
One thing I LOVE searching for when I’m putting together a trip is a list of the most “Instagrammable” or photo-worthy spots in a city.
The reason behind this is because I think it can shed light on areas of the city that aren’t necessarily mentioned in other guides. If you’re hunting for that perfect wall mural or adorable bakery, chances are you’re wandering through a neighborhood where you’ll find all kinds of hidden gems.
I urge you, though, not to get carried away with finding every perfect photo opportunity, though. Kids will tolerate one or two photo sessions on a trip, but they will quickly get bored if that’s all you’re doing.
PUTTING IT ALL TOGETHER
After you’ve done your initial research, you’re likely left with an extensive list of places you would like to visit.
And chances are, there’s no way you’ll be able to do everything on your list within the time allotted.
But that’s ok! One rule I’ve made for myself while putting together itineraries is that we’re NOT going to be able to do everything while we’re there, and that’s ok. We have 3 (soon to be 4) YOUNG children with us, and we often only have a short amount of time to visit a destination.
We usually try to fit in as much as we can, but not at the expense of ruining our trip with crabby kids who haven’t had rest or a nap for days on end.
With that in mind, here are my top tips for putting together the research you’ve done into a coherent itinerary that meets your family’s needs.
BOOKMARK THESE ITINERARY-PLANNING RESOURCES
Viator.com - This website falls under the TripAdvisor company umbrella. Use it to find and book tours, CityPASS cards, day trips, and more.
Get Your Guide - another awesome online travel agency where you can book experiences, tours, and activities.
Airbnb Experiences - if you’re looking for more unique activities hosted by locals, definitely book an Airbnb Experience. You’ll get $10 off your first experience with my link!
Living Social and/or Groupon - find discounts on local activities, tickets, tours, etc.
Google My Map - trip planner where you can create your own map full of the restaurants, activities, hotels, etc. for your trip. (Keep reading for a brief tutorial). You can access this from both your computer and your phone.
Rome2Rio - use this website to help you figure out the logistics of getting from one place to another
KNOW YOUR FAMILY’S PREFERENCES
Each family is looking for something different when they travel. Some are looking for outdoor activities, some are looking for historical sites, still others just want to keep their busy toddler occupied while they see a different part of the world.
Know what each member of your family hopes to get out of the trip before you solidify your itinerary. Perhaps your husband won’t care what Instagram spots he has to photograph for your family as long as he gets to visit a certain museum or brewery. Maybe all you want out of the trip is to sip a cafe au lait at a sidewalk cafe (my only request for our second visit to Paris). Maybe your kids are begging you for a day at the beach.
Take all of this into consideration as you add some things to your schedule and discard others.
USE THE ROCK/PEBBLE/SAND ANALOGY
I’m sure you remember hearing about this in school at some point when a teacher was trying to impress upon the class the importance of time management.
If you have large rocks, some pebbles, and some sand to fit in a jar, you need to start with the large rocks, then fill in space with the pebbles, then fill it up with sand. If you try to reverse the process and put the sand in first, there will be no room for the large rocks.
Of course, the large rocks represent your biggest priorities, the pebbles are of lesser importance, and the sand are activities that are nice but not necessary.
Use the same idea when planning your trip. Go through the activities with your partner or family and decide which few are the most important to you, and schedule those in first. Research when they are open, how much it costs, if you can find any discounts or free days, when it’s most crowded, etc, then add them to your itinerary accordingly.
Next, pick the things you would really like to fit in, but wouldn’t be crushed if you didn’t get a chance to do them. Fill those activities in around the big important ones.
Last, add in the things that looked cool but you personally don’t care whether or not you get to them. If you decide one day you would rather rest than visit that last museum or go back to the beach rather than visit that cafe, no one in your family would complain.
DON’T OVER PLAN
I alluded to this above, but this is extremely important if you’re traveling with young kids. Do not try to pack too much into your schedule. You’ll end up feeling stressed and rushed, and you won’t properly enjoy your experiences because you’ll be worried about getting to the next one “on time.”
Ask me how I know.
Not to mention, everyone, not just young kids, gets irritable when they are tired and hungry with sore feet. It’s just how we’re made.
If you try to push everyone to the limit to get the maximum “enjoyment” out of your destination, just know you will suffer the consequences of crabbiness and whining.
Know your family. Maybe your children are great with stroller naps, and won’t mind getting their rest while you visit an attraction geared toward adults. Conversely, maybe you have a kid that needs at least an hour of nap or quiet time in a dark room with the noise machine going. If that’s the case, try to build that into your itinerary for most days of your trip.
I do believe there are special exceptions where it’s ok to push your family a little bit more to fit in something truly unique or once-in-a-lifetime. In those cases, it’s a valuable lesson in teaching your kids how to go with the flow. Just don’t try to do it EVERY single day of your trip.
BUILD IN DOWNTIME FOR WANDERING
Maybe this style of travel doesn’t work for everyone, but I LOVE having a set period of time to wander through neighborhoods with no particular goal in mind.
Some of my best memories of studying abroad in Quito, Ecuador are when my friend and I would do our best to get lost in the city. We stumbled upon some really cool shops, restaurants, and city streets.
I love that this gives you a chance to just observe and soak in the culture and vibe of a destination without an agenda.
Just make sure you prepare your family beforehand so you’re not answering a million questions as you go (like “where are we going?” “when are we going to get there?”). If they know the goal is to just look around, they may help you find places that catch their eye, too!
MAP IT OUT
One of the last steps is to map out which activities go together based upon their geographical location. Try to group those things together to save money on parking or transportation.
What you’ll want to do is sign into your Google account, then go to Google My Maps (not to be confused with the regular old Google Maps).
Click the red “Create New Map” button in the upper left corner.
Give your map a name where it says “Untitled Map”
Click “Add Layer” to create a category. You could split this up into activities, restaurants, photo spots, hotel locations, etc.
You can color-code each category and even add symbols next to each entry. For example, I have a food/beverage category, but I might put a coffee cup symbol next to the awesome cafe I read about, or a martini glass next to the perfect happy hour spot.
Each layer can be checked or unchecked so you can see JUST activities or JUST restaurants.
Start typing items from your research into the search bar. Google Maps will autofill most of your entries once you start typing.
Once you’ve got everything you want to do entered into your map, you’ll easily be able to tell which points of interest are near one another so you can put together an itinerary that makes sense.
Once you’ve figured out your itinerary, you could even make a second map where each layer is a different day of your trip.
Here’s an example of what our map ended up looking like:
TAKE NOTES
I’ll admit, a lot of my trip and itinerary planning is done online. I save things to Pinterest boards, write notes in Google Docs, map them out in Google Maps, bookmark Instagram photo ideas, and text ideas to my husband.
But that’s the problem. EVERYTHING IS ALL OVER THE PLACE.
Maybe you saved a restaurant to your Google Map that a blogger recommended. Make sure you save it in your notes that the reason you should visit this restaurant is for their one-of-a-kind burger or amazing craft cocktails.
Maybe you included a museum in your plans. Don’t forget to write down if Tuesdays are free or it opens much later than you thought.
Maybe there’s a specific photo spot you want to visit. You wrote down the park, but forgot to include directions from the park entrance to this amazing photo spot.
You need one place to corral all of your notes.
Whether you choose a Trello Board, a shared Google Doc, a simple notebook, or the Family Travel Planner I created for just such instances, make sure you’ve got one organized place for everything you’ll need to know!
CONSIDER TRANSPORTATION
When setting your itinerary, it’s easy to get carried away with planning exciting activities. I often find myself planning the perfect itinerary until I try to figure out how we’re going to get from one place to the next. Then I’m left scratching my head about public transportation or whether we should rent a car, what we’re going to do about car seats, etc.
If you’re confused about how to get from point A to point B, try Rome2Rio to see all the options and their prices laid out for you.
A GREAT ITINERARY MAKES FOR A RELAXED VACATION!
The work you put in ahead of time when it comes to planning your itinerary will pay off in dividends when you’re finally on your trip and can actually relax because all the details have been taken care of!
As moms, (as parents!), we know that travel with kids doesn’t necessarily equate to the most relaxing vacation, but it sure is a lot easier to parent your children in a different setting when you’re not worried about how to get from point A to point B, what time that attraction opens, or where you’re going to eat dinner.
This is definitely something I’ve had to learn over the years as a Type B, go-with-the-flow kind of traveler. I used to think having a plan was the enemy of fun. Now that I have 4 kids, I know that having a plan (a FLEXIBLE plan that you can break if the spirit moves you) is ESSENTIAL to having fun on your travels.
I hope this helps you plan out your next family trip! If I missed any of your favorite resources, let me know in the comments below!
DON’T FORGET IT! PIN IT!
Emily Krause is a Florida-based travel blogger who writes about exploring the world with kids. On A Mom Explores you’ll find best family travel destinations, Disney World tips, and how to make travel with babies and toddlers a little easier.
Emily believes that exploring starts in our own backyards, and adventure can happen anywhere with the right mindset.
