The Best Trips to Take with a Toddler – All of the Family Travel Destinations that Should Be on Your Family’s Bucket List this Year!

I know I know, you’ve all heard “traveling with a toddler? are you crazy?!” but I’m here to tell you you are far from crazy, traveling with a toddler is SO special, so fun, and an incredible way to make precious memories as a family, and have one-of-a-kind quality time. I could go on and on about the benefits of traveling as a family (which you can read more about here) but let me just say that I am so, so grateful for all of the many trips we’ve taken as a family with my little toddler in tow. We’ve been on over 75 flights with our little guy, all around the world, so i wanted to round up my favorite places we’ve been that are all amazing, toddler friendly travel destinations that you need to add to your family’s bucket list! Here’s where to travel with a toddler.

Tokyo, Japan

Japan is one of the most baby-friendly travel destinations in the world. The culture is exceptionally clean, organized, and beautiful!!! It’s an amazing trip to do as a family, and they’re SO friendly toward babies and toddlers. 

We did a trip to Tokyo with our son at 16 months old, but I think it would have been a good vacation spot for babies of any age! Check out our Tokyo itinerary with a toddler here.

Why is Tokyo a good travel destination with a toddler

The culture in Japan is very toddler-friendly, the public transit is super easy (and stroller friendly, too!), and the entire city is walkable as well if you want to get your steps (and stroller naps) in! We thought it was such a great destination for our family. Tokyo is packed with exciting interactive museums (like the one pictured above – that my son LOVED!!!), kid-friendly attractions, lots of parks to walk to, and even Tokyo’s Disneyland if you’re feeling up for that adventure! 

The best time of year to visit Japan with a toddler

The best time of year to visit Japan is April-May or September-October, when temperatures are mild, there isn’t much rain, and skies are generally clear and sunny!  Any time of year is beautiful in Japan, but my favorite season to visit is cherry blossom season (April/May) or fall in Japan! We did Tokyo as a family in October and the weather was absolutely gorgeous.


If you’re looking for a warm escape as a family and want an easy trip full of relaxation (much-needed for any toddler mamas and dadas, especially!!!!), Mexico is a perfect choice for your family vacation! We’ve been to Mexico a few times with our son Harrison and each time is so amazing. He loves it, and the hotels in Mexico are so good and accommodating with kids and babies! 


Where to stay in Mexico with a toddler


The Rosewood Mayakoba

If you’re looking for a luxury resort in Mexico that will exceed every one of your expectations, and is EXCEPTIONALLY baby, toddler and kid friendly, but super luxurious at the same time, I can’t recommend the Rosewood Mayakoba highly enough. We headed to Mayakoba when my son was just a few months old as our first international trip with a baby, and I knew immediately that we would be back when he was a toddler as well. The impeccable service at this resort is simply next-level, and they really prioritize families in the most incredible ways. They have everything you need!!! And their service goes above and beyond to be sure to give your family the vacation you deserve, including encouraging you to use their super-talented on-site nannies available, which we loved using! 

Make sure you take some time to yourselves to go to the spa, which sits on its own private island overlooking beautiful, lush, lagoons! It’s gorgeous.

BTW, for free breakfast for two at the Rosewood, a $125 resort credit, and a room upgrade (if available), fill out this contact form and be sure to use the referral code “JETSETCHRISTINA” if you use my referral, my agency partner will reach out with more information and can help book you with all kinds of fun perks (at no extra cost to you, and they don’t charge a fee to book!)

The Waldorf Astoria Pedregal Los Cabos

The Waldorf Astoria Pedregal Los Cabos is a stunning hotel nestled on Cabo’s gorgeous Pacific Coast, in the prestigious, super-safe gated resort community of Pedregal. This resort is amazing, and we love it here so much (we went on a family trip here, and also babymooned here!)

And ALL the rooms at the Waldorf have an in-room plunge pool! SOOO fun for your little one. My son loved ours, which was always a balmy 85-90 degrees (perfect for babies!). 



For families and multi-generational groups looking for a Mexico all-inclusive resort that’s good with families, I’d always recommend choosing Finest Playa Mujeres! I loved this hotel and it is the only all-inclusive luxury family friendly resort in greater Cancun, and the only one of the three resorts that isn’t adults-only!

It’s easy to see why young families are drawn to Finest – not only do they have the most expansive and beautiful kids club I’ve ever seen (waterslides, movies, round-the-clock activities, full-time nannies at no additional cost (!!!!!!!) & the option to stay with your kids if you want to!), but the family-friendly atmosphere throughout the resort is one that will make every family want to come back year after year. 

Disney World

We just got back from our first trip to Disney World with a toddler, and let me tell you, I cannot recommend it highly enough – doing Disney World with a toddler was nothing short of MAGICAL!!!!!!!! Now, let me preface this by saying my husband and I are not overly “Disney” people, we love Disney movies, sure! But Harrison, our son, hasn’t seen any yet (he’s 19-months-old, and hasn’t been doing screens) and we aren’t overly obsessed with Disney in our house. That being said, my husband and I both have the most special memories of visiting Disneyland and Disney World as kids with our parents and grandparents, and we knew this was something we wanted to share with our family when it came to traveling with our baby boy. 

We waited until our son was a year and a half or so to go, and I’m so glad we did. He was the PERFECT age at 19 months it felt like for his first Disney World trip. I think anywhere between 18 months and 3 or so is a really fun age to go on your first Disney trip! He was aware enough to really take it all in and ENJOY every second of it, but he was still little enough that it all felt SO real to him.

Ahead of the trip, we started to introduce him to Mickey and Friends and Winnie the Pooh through books and music and such, and he quickly fell in LOVE with all the characters – especially Mickey. His favorite song is “Hot Dog” by Mickey and Friends and he sings it all the time!!! Ahead of the trip, he had a little Mickey that he would NOT let go of, he carried all around Disney World with him too, and even showed it to the ‘real’ Mickey when he met him – soooooo sweet!!!!! This little connection to Disney definitely made the trip all the more special, and I’m sure on our next trip he’ll have lots more Disney characters that he loves and is obsessed with!


We took it pretty easy on our first trip to Disney World (you can read all about my tips for doing Disney World with a toddler here) and chose to only do one day at the parks at Magic Kingdom, which was more than enough – we were exhausted and all had the BEST day!!!!!!

The other days, we played at the resort pool (this is where we stayed, which was EPIC, they had a huuuuge splash pad that he was obsessed with, a baby slide, a lazy river, and a biiiig family friendly pool. I think my son enjoyed the resort days just as much as the park days!!!! And we even did a character breakfast (which they hosted at our hotel – huge score! one of the other days too, so he got to hang with Mickey and Minnie and Goofy again!

The best time to visit Disney World with a toddler:

We went in the off-season (January) and I loved not having to fight the insane crowds (both at the resort and at the parks) it wasn’t empty, don’t get me wrong (Disney is always going to have crowds, 365-days-a-year), but it’s always great to get it in the more shoulder season where you aren’t standing in 2-hour lines all day long. 


Hawaii is a perfect destination for families with a toddler. I grew up traveling to Hawaii as a little girl (at least once a year!) and I have the BEST memories of Hawaii with my family. Now, traveling as a mother with my own family, I always come back to Hawaii as where I want to go back to time and time again – I think there’s no vacation like Hawaii when it comes to traveling with a toddler. 


Where to stay in Hawaii for a family vacation


On Maui, we love the Four Seasons Maui and it is similarly super family-friendly!

The Four Seasons Maui is our home away from home – we love it so much.

And while that’s my favorite for the ultimate in luxury, if you’re looking for a resort with a less pricey room rate, I also love the Westin Kaanapali and the Grand Wailea is fab for toddlers too! ( so many fun pools!) 

The Big Island

Four Seasons Hualalai is my favorite pick for a Big Island hotel with a baby or toddler (we have stayed here in the past and it is absolutely dreamy!!). Here, they’ll make it super easy for you every step of the way – they have everything to make your stay more comfortable, from a crib, playpen, diapers, wipes, a white noise machine, a bottle warmer, “little swimmers” diapers for the beach/pool, a nursing pillow, and a high chair! and… EVEN FREE WASHERS/DRYERS throughout the resort!! This is an incredible convenience for a family because all of these things means less packing/stressing for you when traveling with a baby!

BTW – For free perks like breakfast for two, a $100 resort credit, and a room upgrade (when available), fill out this contact form and be sure to use the referral code “JETSETCHRISTINA” if you use my referral, my agency partner will reach out with more information and can help book you with all kinds of fun perks (at no extra cost to you, and they don’t charge a fee to book!) This goes for planning trips to other destinations and hotels too! 

Palm Beach, FL

We recently did a trip to the Four Seasons Palm Beach in Florida and had the best time with our 19-month-old. He THRIVED at their big family pool and in their toddler room (they have a “Kids for All Seasons” area which has a fun toddler room full of toys, a slide, etc. He would meet other little resort friends there, too it was precious. This hotel had everything figured out for toddlers (and their parents) the crib was extremely comfortable for him (he slept perfectly all of the nights, which he doesn’t usually do at home!) and they even had a white noise machine, a diaper pail, and pouches and a stuffed doggy for him when we checked in! He was in heaven!!!! If you’re looking for a luxe getaway traveling with a toddler without leaving the US, with good food, a good beach, and nice weather year round, definitely check into the Four Seasons Palm Beach. 

Shop our matching family outfits below!


Charleston is one of the most toddler and kid-friendly destinations in the USA, and makes for a perfect getaway with family (or a multi-generational getaway, or a group trip with a couple families!). With the best food scene in the US (you can read up on my Foodie Guide to Charleston here), gorgeous colonial architecture, the nearby beaches, and of course, the quintessential Southern hospitality, there’s nowhere quite like this charming Southern city.

Where to stay in Charleston with a baby

I highly recommend Wild Dunes for a buzzy fun, family-friendly resort on right on the beach when traveling with a toddler. You’ll be 25 minutes from downtown, and I think it’s worth the extra distance to downtown to stay on the beach (especially with toddlers!) Also, their kid pools here are absolutely amazing. If you want to spend time downtown, you could also split your time and do half the time at the beach, half downtown. 

Also tucked away from the city is the beach destination of Kiawah, which is super baby and toddler friendly as well. Read all about our hotel stay at Kiawah Island with a baby here.

The best time of year to visit Charleston with a baby

I recommend May and June or September and October for visiting Charleston with a baby! This way, you’ll have beautiful weather but without the high humidity heat that the summers in Charleston bring.

The Caribbean 

Nothing hits the spot more when traveling as a family than a white-sand-beach relaxing vacation in paradise, and the Caribbean is your spot for that. Here is where I would go when traveling with a toddler!


Anguilla is one of the most beautiful islands in the Caribbean, and will always be my pick for white sand beaches and warm weather. I highly recommend the Four Seasons Anguilla (specifically the residences and multiple bedroom villas) for a family-friendly luxury resort. We went for our babymoon to Anguilla and absolutely LOVED it. We both said we couldn’t wait to come back with our baby because the beaches here are so baby friendly! 

St. Martin

St. Martin in the Caribbean is a great choice with a baby or toddler because it has calm beaches, nice water, and a family-friendly atmosphere. The Belmond La Samanna is the nicest resort on St. Martin and where we stayed with our son and had the BEST time. Belmond La Samanna is a gorgeous, luxe resort tucked onto the absolutely stunning beach of Baie Longue. Belmond never misses, but this is one of my favorite hotels (especially when traveling with a toddler!) There are 83 beautifully-decorated ocean-view guest rooms, suites, and multi-bedroom villas, and all of the pool areas here are colorful, chic, tropical, and make for a great Caribbean vacation

A picture of a blue beach with a woman and a toddler featured for a content about traveling with a toddler. A picture of a family on a beach featured for a travel content about traveling with a toddler.

What Makes St. Martin family-friendly?

Yes! St. Martin is one of the most family-friendly destinations in the Caribbean, and a great spot for little ones due to its calm beaches, soft sand, kid-friendly restaurant scene, and warm weather. We had the best time traveling to St. Martin with our baby – who was 11 months old at the time. The hotel (Belmond La Samanna) felt extremely safe and found it very baby-friendly! 


Check out these other blog posts:

Why you should travel with a baby (and do it often!)

The best places to travel with a baby


12 Key Tips for Visiting Disney World with a Toddler for the First Time


The Ultimate Jetset Guide to Disney World - How to Do Disney World Luxuriously & Stress-free


Christina is a leading luxury lifestyle and travel blogger with over 2 million readers. Follow her on instagram @jetsetchristina.