Traveling with a toddler is no joke! It can be a lot of work, but it is ALWAYS sooo worth it! As a luxury travel advisor and mom, I think the key is choosing a toddler friendly destination to ensure everyone has a great time.
My husband and I traveled as a couple together for a decade before having our daughter. We have a pretty specific travel style – we love intimate hotels, amazing restaurants and exploring a city the way a local would – not necessarily doing all the touristy things!
When it came to vacations with our toddler, we wanted to pick destinations that she would enjoy and where we wouldn’t be stuck doing cheesy “family-friendly” things the whole time (like aquariums, theme parks and zoos 🙃).
But, where we could play on the beaches of Greece, or relax in the rolling hills of Tuscany, or explore historic castles in Denmark together. No, they won’t remember it, but it’s about our memories too and enjoying the moment together!
I’ve rounded up a list of the places we’ve traveled with our toddler daughter and LOVED to help inspire your family adventures! So far, she’s traveled across 3 continents before 19 months old!
In this guide to the best places to travel with a toddler, I’ll share all about when to visit each country, where to stay with a toddler and the best kid friendly things to do in each locale. And if you’d like someone else to handle the logistics of planning, I’m a travel advisor and would be glad to help.
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These are my favorite places to travel with a toddler!
Let’s get started! Here are our favorite trips with a toddler, plus a few on our bucket list from our friends recommendations!
1. Copenhagen, Denmark
I’ve been to Copenhagen almost every year since 2019. It’s one of our favorite places to visit plus we have family friends that are Danish so we love an excuse to visit them! When it came time for our first Europe trip as a family vacation, Denmark was our first stop and our daughter’s first passport stamp!
We booked this trip before she was even born so we knew somewhere familiar to us would be a great choice. Copenhagen is fantastic for kids with a clean walkable, bike-able, and stroller friendly city.
There are so many amazing restaurants and plenty are welcoming to little ones. Not to mention, there are several family friendly activities like fairytale amusement park, Tivoli Gardens, Deerhavyn, and amazing playgrounds.
When to Visit Copenhagen with a Toddler
The best time to visit Copenhagen is in the summer months from May through September. I’ve been to Copenhagen in each of these months, but we took our toddler in early September.
We enjoyed great sunny weather and mild fall-like temperatures. It was perfect for stollering her everywhere and enjoying outdoor activities. Denmark gets very cold in fall and winter so it’s not as ideal for a toddler or baby.
Where to Stay in Copenhagen with a Toddler
Villa Copenhagen Hotel
We’ve stayed in a couple hotels in Denmark, but we chose Villa Copenhagen when traveling as a family. We loved that this hotel had a rooftop pool so we could take our daughter.
They were very family friendly offering a crib with sweet blankets for her. And even a child sized robe for the pool! Though, the rooms are a bit small so definitely opt for a larger suite.
It’s right next to the train station and Tivoli Gardens making it an ideal location for convenience. We walked everywhere whether to Nyhavn or the Meatpacking District from Villa Copenhagen.
Things to Do for Kids in Copenhagen
These are some of the best activities for kids in Copenhagen:
- Playgrounds – if you’ve not seen a Danish playground, Google it! These things are so well planned and so much fun that I actually want to take my daughter!
- Tivoli Gardens – We’ve visited Tivoli even before having a child. It’s one of the oldest amusement parks in the world and inspired Walt Disney. It’s so charming and quiant!
- Deerhavn – our friends brought us to Deerhavn for lunch and a carriage ride through the countryside here. The park is where the King’s summer home is located and the property is open to the public to wander the grounds. There are hundreds of wild deer roaming the grounds and it’s so cool for kids!
- Canal Cruise – we love a canal cruise, but skip the touristy boats with a baby and take this private tour on a wooden boat!
- Rosenborg Gardens – this is my favorite castle in Denmark. Your kids wont care to tour, but they’ll love running around the gardens and surrounding property. Bring a blanket and spend the afternoon having a picnic while admiring the castle.
Planning a trip with a toddler? 🤍
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As a luxury travel advisor and mom who travels with young kids, I can help you choose the right destination and hotel for your family. I can also add travel advisor perks like complimentary breakfast, potential upgrades and hotel credits when available.
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2. Greece
We took our daughter to Greece at 11 months old and it could not have been more perfect. The Greek Islands are fantastic for children with miles of coastline and sandy beaches to enjoy! It is one of the best international places to travel with toddlers.
We visited Sifnos for 5 days and spent 2 nights in Mykonos at Cali Mykonos Hotel. We’d been to Sifnos before so knew it would be perfect for her first European summer trip! We also had friends join with their 2 year old and our girls loved playing on the beach together.
Sifnos is known for its amazing beaches and foodie scene. It’s a lesser known island so you can avoid some of the crowds by visiting here which is especially nice with kids.
One of our favorite days was spent at Faros Beach. We got a table at Pelicanos which is literally in the sand right next to the shore in a shady spot. It was perfect for kids to enjoy food, drinks for us, and not have to sit still at a table because they could play in the sand!
I recommend trying to skip Athens with a toddler vacation. They won’t care about the Acropolis so unless you really want to see it, I would personally avoid the big city!
When to Visit Greece with a Toddler
The high season for the Greek Islands is the summer. From about May through October are the absolute best warm months.
We always go in September because most Europeans have taken their holidays already and kids are back in school. It’s less crowded!
Plus, I like September because the water temperature has had all summer to warm up. If you went in May, it might still be cooler for swimming.
Where to Stay in Greece with a Toddler
We stayed at Verina Astra the first time we visited Sifnos, and it was so special that it made us want to return! Fun fact: we actually booked the hotel before our daughter was born—without realizing they don’t typically allow children. Always double check that when booking with kids! Thankfully, they made an exception for us and were incredibly kind.
Next time, I’d book NOS Hotel in Sifnos or Verina Villa, which is ideal for families and offers plenty of space to spread out.
Here are a few of the best family-friendly hotels in Greece to check out:
- Cali Mykonos – They were so welcoming to our toddler and have the longest pool in Greece!
- Four Seasons Astir Palace – Close to Athens and perfect for a luxurious
- Phae Blue Elounda (Crete) – Spacious suites and private pools, plus kids’ activities and an amazing beach.
- Daios Cove (Crete) – Excellent for families with a kids’ club, private beach, and plenty of family-sized villas.
- Canaves Oia Epitome (Santorini) – Offers villas with private pools in a quieter part of Santorini, great for families wanting luxury and privacy.
Things to Do for Toddlers in Greece
There are plenty of fun things to do in the Greek Island for kids like:
- Beach Days – you’ll spend most of your time playing on the beach
- Pool Days – definitely book a hotel with a pool
- Exploring historic sites (better for older toddler) – the islands have many historic sites (especially on Rhodes) which would be fun for older toddler to wander around.
- Exploring Villages – Strolling through charming villages
- Sailing (depending on age) – Spend a half day sailing around the islands if you’re toddler is old enough.
3. Japan
We recently took our toddler to Tokyo and Kyoto, Japan at 19 months old. While the flight was long, it was sooo worth it! Japan is so wonderful for babies. It’s clean, safe, stroller friendly and just such a wonderful place for families if you’re up for the flight.
What stood out the most was the hospitality. Every hotel was so kind to make special meals for our child – usually steamed broccoli. They also offered cribs, baby soaps, diaper pails, toddler towels, etc to make our stay more comfortable.
Every single person who passed on the street smiled and waved at her – it was unreal! Not just baby friendly, but truly WELCOMING! It was the best feeling.
At her age, she loved being pushed around in her stroller, running around at parks and shrines, and soaking everything in! It was perfect because we got to see so many cultural sites, while she enjoyed being outside and running around them!
👉 Read our Tokyo Itinerary and Kyoto Itinerary, plus tips for visiting Japan with toddlers!
When to Visit Japan with a Toddler
The best times to visit Japan are April & May (spring) and September & October (fall). These months have the most pleasant temperature for exploring with a little one where you don’t have to bundle them up or cover them in sunblock.
April is known for cherry blossom season and is the busiest time to visit. We went at the end of April, right after the season and it was much less crowded (as locals told us) plus we still saw some cherry blossoms. And the azaleas were blooming and they are ALL OVER Japan so it’s really stunning! I’ve heard fall is incredible too with tons of foilage!
Where to Stay in Japan with a Toddler
We visited Tokyo and Kyoto with our toddler and this is where we stayed in each city. We did Tokyo on the front and back end of our trip so did two different hotels!
- The Shinmonzen (Kyoto) – hands down best ultra luxury hotel I’ve stayed at. Traditional ryokan style inn which is a must in Japan! Has only 9 rooms so it’s very intimate and safe. We loved the Michelin star restaurant and outdoor terrace we could enjoy during nap times! The staff here were just above and beyond!! Read my Shinmonzen Review here.
- Four Season Tokyo at Otemachi – Four Season is always a good choice and this hotel was fantastic. They upgraded us to a room with an amazing view of the Imperial Gardens and included a crib plus other baby amenities for our toddler. It sits above a metro station which was so convenient for getting around! Read my FS Tokyo review here.
- Tokyo EDITION Ginza – We stayed here for one night and it was great. The EDITION hotels are so chic, but this one was smaller and more of a boutique feel. Ginza location was ideal for walking to Tsujiki Market and exploring the high end Ginza area. See my Tokyo Edition hotel review here.
Things to Do for Kids in Japan
- Tokyo Disneyland – if you’re up for it Tokyo Disneyland is amazing. We didn’t have enough time and she was a little young, but an older toddler would love!!
- Kyoto City Zoo – We had a good time at the zoo showing her animals for an hour. We saw elephants, giraffes, zebras, monkey, flamingoes and more! She was entertained.
- Visit temples and shrines – I loved seeing the amazing shrines and temples of Kyoto. My daughter loved running around them and getting some energy out! Win-win!
- Local Parks – There are so many local parks and green spaces around both Kyoto and Tokyo. We loved Yoyogi Park in Tokyo and Maruyama Park in Kyoto.
- Imperial Gardens – Imperial Gardens is the grounds where the royal family lives. It’s a great place for kids, but it is NOT open all the time. Be sure to check dates and times as they vary!
4. Charleston, South Carolina
As a Charleston local, I can’t tell you enough how great this city is for little ones! It’s easily one of the best vacation destinations with a toddler in the USA. There are so many young families here so there’s tons of great parks, kids friendly restaurants and tons of historic site to explore. If you’re planning a beach vacation, Charleston has 5 area beaches to suit your style.
For a beach trip, I would head to Kiawah Island Golf Resort and stay at the Forbes 5 Star hotel, The Sanctuary. The resort hotel is beachfront with miles of coastline, biking trails, pools, and kids camp activities. It’s so ideal for families that want an adult and kid friendly place to visit. They also have villas on site which are great if you’d like space to cook meals or have multiple children.
From there, you could do a day trip to downtown Charleston or visit the nearby plantations and gardens like Magnolia Plantation.
When to Visit Charleston with a Toddler
The best times to visit Charleston with a toddler are April & May or September & October for the most pleasant weather to explore downtown Charleston.
The summer months are great if you are spending time at the beach. However, it is VERY hot and humid so it’s best to spend your time at the beaches in June, July and August.
If you want to take a Christmas trip, Charleston is amazing at Christmas with plenty of activities your toddlers will love.
Where to Stay in Charleston with a Toddler
These are my favorite family friendly hotel in Charleston:
Downtown Charleston:
- The Charleston Place – This iconic hotel is as family-friendly as it is luxurious. You’ll love the central location, indoor pool, and Southern charm.
- The Cooper (opening 2025) – I’m already excited about this new waterfront hotel. It’s expected to be stunning and walkable to everything downtown.
- The Restoration – Apartment-style suites make this ideal for families. Full kitchen, living area, and separate bedrooms mean space to spread out and unwind—especially helpful during nap time!
Beach Resorts:
- Kiawah Island Golf Resort – A luxury beachfront escape with pristine Lowcountry scenery. It’s more exclusive and peaceful, about 40 minutes from downtown Charleston. Great for families who want nature, space, and five-star service.
- Wild Dunes Resort – A more affordable, family-focused beach resort just 25 minutes from downtown. Think ice cream shops, big pools, beach bonfires, and bike rides—this one is made for memory-making with kids.
Things to Do for Kids and Toddlers
- Magnolia Plantation and Gardens – best Charleston plantation for kids with natural tram ride, Audubon swamp and small petting zoo.
- South Carolina Aquarium – truly a special aquarium done really well. Showcases animals native to the Lowcountry like otters, sea turtles, a stingray touch tank and more!
- Children’s Museum of the Lowcountry – we’re annual members here and it’s such a great place for kids to play that is all about Charleston.
- Fire Museum – houses really cool vintage fire trucks – little boys will love!
- Charlestowne Landing – where Charleston was founded by the initial settlers. Great for kids to run around outside, visit the small zoo with native animals like bison!, and explore the 17th century replica ship
- Beaches – the beach is always great for kids in any season! Head to Sullivan’s, Folly, or IOP for the closest beaches.
LEISURELY TIP: if you reach out to my travel agency, I can help book your hotel (without any fees) and can get the best rate, plus awesome perks like complimentary upgrade, free breakfast and resort credits. Ask us about it and we’ll be happy to check hotels and rates for you with no strings attached!
5. The Caribbean
The Caribbean is always a great toddler destination especially if you live on the East Coast or your city has a direct flight to an island. You really can’t go wrong, so I’d pick any island that’s convenient for you to get to so can maximize your vacation time!
If your child does not have a passport, there are several US territories you can visit without one like Puerto Rico or the US Virgin Islands!
My favorite islands are Puerto Rico, the Bahamas, Barbados, Anguilla, St Barths, and Turks and Caicos. There are so many amazing options and family friendly resorts across the Caribbean.
When to Visit the Caribbean with a Toddler
The best time to visit is in the winter from December to about March! Summer is very hot and fall brings hurricane season you’ll want to avoid June-October to ensure no trip interruptions.
Winter season will offer you nice warm 80 degree tropical days and sometimes cooler evenings!
Where to Stay with a Toddler in the Caribbean
Looking for sun, sand, and seriously family-friendly luxury? These resorts in the Caribbean are perfect for a trip with your toddler. From calm beaches to thoughtful kid amenities, these spots make island life easy and relaxing for parents, too.
- Belmond Cap Juluca (Anguilla) – Calm turquoise waters, soft white sand, and spacious suites. This spot is peaceful, luxurious, and ideal for little ones who love the beach.
- Rosewood Le Guanahani (St. Barths) – A chic yet family-welcoming resort with calm coves and a gorgeous kids’ club. It’s proof that St. Barths can absolutely work for families.
- The Dunmore (Bahamas) – A charming boutique resort on Harbour Island. Think pink sand beaches, laid-back elegance, and a warm, friendly vibe.
- Rosewood Baha Mar (Bahamas) – Perfect if you want resort amenities and ease. There’s a beautiful beach, shallow pools, and everything from baby gear to babysitting on request.
- Six Senses La Sagesse (Grenada) – This newer property brings Six Senses’ signature wellness and sustainability with a family twist. Great for adventurous families ready to explore a less crowded island.
Things to Do for Kids in the Caribbean
A trip to the Caribbean with a toddler is all about slowing down and soaking it all in.
Expect lots of time splashing in shallow pools, building sandcastles on soft beaches, spotting fish and birds, and enjoying the warm breeze. Many resorts offer nature walks, kids’ clubs, and beach toys.
Even meals can be fun—toddlers will love trying tropical fruits and local dishes like beans, rice, and fresh seafood (if they’re up for it!). It’s a trip that’s as fun for them as it is relaxing for you.
Planning an easy beach trip with your toddler? Let me handle the hotel.
The Caribbean may feel like an easy vacation to plan, but choosing the right resort with a little one can make or break the trip. I’ll help you find a hotel that fits your family, book it for you and add my VIP perks when available, so you can skip the hours of research and feel confident you picked the right place.
You handle the packing. I’ll handle the hotel. 🤍
6. Switzerland
We’ve been to Switzerland multiple times and driven all over the country so I know it will be so much fun for toddlers. Switzerland is super clean, safe, and unbelievably scenic. It’s also stroller friendly and easy to explore by car or train, which makes it such a great destination for families.
Summer is ideal for toddlers because you can really take advantage of the incredible weather and outdoor spaces. There are lakes to swim in, car-free mountain towns to explore, and plenty of room to run and roam.
Geneva is our favorite city and we just love the vibe there. But we also adore Bern, Lucerne, and Zurich. Each city is compact, charming, and full of family-friendly activities.
When to Visit Switzerland with a Toddler
Summer is the best time to visit Switzerland with kids. June through early September has the most pleasant weather for hiking, lake days, and outdoor play. You won’t have to worry about bundling them up or managing cold-weather gear—just let them explore!
If you go in early summer, you’ll still catch some snow in the higher Alps while enjoying sunshine down in the valleys. It’s the best of both worlds!
ALSO SEE: 5 Day Switzerland Itinerary
Where to Stay in Switzerland with a Toddler
We’ve stayed at some incredible hotels in Switzerland and these stood out for being family friendly while still offering that luxury experience we love.
- Hotel Longemalle (Geneva) – We love this boutique hotel right in the heart of Geneva. It’s stylish, welcoming, and walkable to the lake and parks.
- Hotel Storchen (Zurich) – Right on the river in the old town, this hotel is charming and very comfortable for families. It’s also easy to get everywhere from here – just step outside and explore!
- Bürgenstock Resort & Alpine Spa (outside Lucerne) – This place is just WOW. We weren’t sure if it would be kid friendly with its luxury vibe, but it completely is. There are outdoor pools with stunning views, a funicular, and they’ll even setup a play area for kids in the family suite.
Things to Do for Kids in Switzerland
- Paddle boats + lake time – Most Swiss cities have lakes and rentals available.
- Mountain trains and gondolas – Kids love the adventure of taking cable cars or mountain trains. Plus, the views are incredible for everyone.
- Old town strolls – Cities like Bern and Lucerne have adorable old towns that are stroller friendly and full of charm.
- Parks + green space – Switzerland is full of beautiful parks and playgrounds. They’re clean, safe, and often have epic views.
- Boat ride on Lake Geneva – This is such a peaceful, beautiful experience. Great for older toddlers who can follow instruction better.
Traveling with a toddler is already a lot. Planning the trip shouldn’t be.
If the thought of comparing 47 hotels, figuring out the best location, planning around nap times and wondering if a hotel is actually good for families has you overwhelmed, that’s where I come in.
I can help you find the right hotel or take the planning completely off your plate with a custom itinerary designed around your family. Reach out here!
7. Santa Monica, California
We recently visited Santa Monica as a family and totally fell in love with it. I hadn’t been to LA before and now I get the hype! Santa Monica has such a relaxed vibe, great weather, and it’s incredibly walkable and stroller friendly, which made it so easy with our toddler.
We stayed at the brand-new Regent Santa Monica and I was blown away by how kid-friendly it was. They welcomed our toddler with a tray of toys to choose from at check-in (so sweet!), had a Nestig crib with an adorable mobile set up in our room, and even included baby toiletries with little balloons tied to them. It was thoughtful, fun, and made us feel so taken care of.
We loved walking along the beach, visiting the famous pier with its carousel and rides, and just strolling around the area. Everything felt easy and fun and our toddler had the best time.
When to Visit California with a Toddler
Santa Monica is lovely year-round, but spring through early fall is ideal. Think sunny days, mild ocean breezes, and perfect beach weather without needing to pack layers.
We went in the spring and it was warm enough for beach play during the day but cool and comfortable in the mornings and evenings which is great for toddler naps and walks!
Where to Stay in California with a Toddler
Regent Santa Monica
Regent Santa Monica – I can’t say enough good things about this hotel. They made our daughter feel like a VIP from the second we arrived. Between the toy tray, crib setup, and baby amenities, it was honestly one of the most toddler-welcoming hotels we’ve ever stayed at. It’s also in a perfect location to walk to the beach and pier.
Things to Do for Kids
- Santa Monica Pier – The pier is such a classic! Our toddler loved the carousel and just watching all the action. There are small rides, games, and lots of space to wander.
- The Beach – Playing in the sand was a huge hit. The beach is wide and clean with plenty of room to spread out and let your little one dig, run, and splash.
- Strolling around town – The whole area is flat, walkable, and stroller-friendly. We loved popping into shops, grabbing snacks, and just exploring the palm-lined streets together.
- Palisades Park – This clifftop park has gorgeous ocean views, open space to play, and a peaceful vibe for a sunset walk or morning stroll with coffee in hand.
Also see: Places to Visit in the USA
8. Italy
We’ve been to Italy before, but this September was our first time going as a family and I was so excited to see it through our toddler’s eyes! We visited Lake Como, Florence, and Tuscany, and had so many fun, kid-friendly plans. Think boat rides, a cooking class, pool time at a villa, and lots of strolling through beautiful towns.
Lake Como was a dream with a toddler! Think: slow mornings by the lake, cruising around on a boat, and hopefully a family photo session to capture the magic. In Florence with a toddler, we planned to stroll past the Duomo, visit some parks, the famous carosel, peek into wine windows, and let our little one soak up the lively city vibe from her stroller. Tuscany was all about space to run, swim, and relax. The villa we stayed at has a pool and tons of outdoor space, perfect for little ones. We especially loved exploring Siena with our toddler and her cousins!
And I’m probably most excited about the kid-friendly cooking class we booked! What a special way to make memories as a family!
When to Visit Italy with a Toddler
September is one of the best months to visit Italy with a toddler. The summer crowds have thinned, the weather is warm but not scorching, and everything is still in full swing.
It’s ideal for being outside – whether you’re wandering a city, cruising on a boat, or relaxing in the countryside. Evenings are cooler and perfect for dinners al fresco with a sleeping baby in the stroller.
Read all about our family babymoon in Lake Como here!
Where to Stay in Italy with a Toddler
- Il Sereno (Lake Como) – We were so excited to stay here and it exceed expactations. It’s right on the water with a chic but relaxed feel. Perfect for parents who want luxury with a family-friendly vibe. Read my full review of Il Sereno.
- Villa in Tuscany – We stayed at a private villa with a pool and lots of open space—perfect for letting kids run free while the adults sip wine and take in the views.
- Collegia alla Querce, Auberge in Florence – This brand new boutique hotel feels warm and personal, with a great location for exploring Florence on foot. We LOVED staying here with our daughter.
Also worth considering: the new Lake Como EDITION (stunning and walkable to town) and the Four Seasons Firenze, which has a private park and is known for welcoming families with open arms.
Things to Do for Kids in Italy
- Boat ride on Lake Como – Our toddler is going to love riding on the water and seeing the little towns along the lake. It’s such a relaxing way to explore.
- Visit the Duomo in Florence – A beautiful spot to walk around while your little one enjoys the open piazzas and all the street musicians!
- Family photo session – Italy is so photogenic. Booking a family session while you’re here is such a fun way to capture the memories.
- Kid-friendly cooking class – We’re doing one in Tuscany and I can’t wait. It’s hands-on, fun, and great for toddlers who love to help.
- Pool + outdoor play – Whether you’re at a villa or hotel, pool time is always a win with kids. Tuscany especially offers so much space to roam.
✨Need more tailored advice? As a luxury travel advisor, I would love to help you plan your family getaway or simply help find the right hotel and get you access to my VIP perks like complimentary upgrades, free breakfast, and more! Inquire here to get started no matter your destination!
9. Germany
We visited Munich with our baby last September and had the best time! It was such an easy, fun city to explore as a family- walkable, clean, and filled with parks and pedestrian zones. We saw the sights, ate our weight in pretzels, sipped German beers, and even found the cutest baby shops while strolling around!
Plus, we got to try so many amazing restaurants (even Michelin star spots) that allowed little ones!
We stayed at the Rosewood Munich, and it was incredible. Sooo family friendly! They had a beautiful crib set up in our room, plus thoughtful extras like a diaper pail, bottle warmer, baby bath products, swim diapers for the pool, and even a potty training toilet. I was most impressed by the bath tub mat so we could bathe her safely!
The staff went above and beyond—they offered purees for our baby and had great kids’ menus too.
We loved that we could walk everywhere from the hotel to Marienplatz, the English Garden, and all the charming streets in between. It made sightseeing so easy and enjoyable with a stroller.
When to Visit Germany with a Toddler
September was the perfect time to visit Munich. The weather was mild and crisp, perfect for walking and park time without overheating or bundling up.
You might catch the beginning of Oktoberfest (fun fact: it begins in September) but the city still feels manageable and family-friendly during the day.
And of course, December is a dreamy time to visit for the Christmas markets. Munich turns into a festive wonderland with twinkling lights, mulled wine, and all the holiday magic.
Where to Stay in Munich with a Toddler
Rosewood Munich
Rosewood Munich – Truly one of the most family-focused luxury hotels we’ve stayed at. From baby gear to kid-friendly dining options, they thought of everything. The location was ideal being close to all the sights but tucked away enough to feel calm and restful.
Things to Do for Kids in Munich, Germany
- English Garden – This massive park is a great place to walk, let toddlers run, or sit by the river for a picnic. There’s even a spot to watch surfers ride the standing wave, which fascinated our baby!
- Marienplatz – The heart of Munich with its famous Glockenspiel. It’s a fun spot to stop and watch the clock show (and the crowds!)—great entertainment for little ones.
- Stroll and Shop – Munich has lots of charming pedestrian areas with cute baby stores and toy shops. We picked up a few adorable souvenirs for our little one.
- Eat Pretzels + Drink Beer – There are plenty of kid-friendly beer gardens where you can enjoy a cold drink while your toddler snacks on pretzels and plays nearby.
Also read: My 3 day Munich Itinerary with a Baby
10. Bermuda
We recently visited Bermuda with our daughter (2.5) and newborn son (4 months), and it was such a fabulous family trip. It was our first trip as a family of 4 with a toddler and baby! We chose it because it’s an easy long weekend getaway from the East Coast—and especially from Charleston where we live. There are direct flights from ATL, CLT, NYC, BOS and more, and it’s only about 2.5 hours in the air!
Bermuda is not in the Caribbean, but it absolutely has that same tropical feel. The water was unbelievably clear, and the sand was that soft pink tone you always see in photos. We went in May (their season runs May–October) and the weather was perfect—around 72 degrees, sunny, with a constant breeze so it never felt hot, sticky, or humid.
We stayed at the Rosewood Bermuda and it was absolutely perfect. They have an incredible beach club, and our suite even came with a golf cart, which our daughter LOVED. We used it to go back and forth across the resort whenever we wanted—it made everything so easy. The resort also has four pools, including a zero-entry toddler-friendly pool that was perfect for splashing. They also offer a kids club for ages 3 and up.
There’s plenty to do in Bermuda if you’re feeling more adventurous (we kept it pretty relaxed this trip), like exploring St. George’s, Hamilton, the pretty churches and cobblestone streets, limestone caves, lighthouses, and more. Everything feels safe, easy, and scenic to explore with kids.
Things to Do for Kids in Bermuda
Beach + pool time – Honestly the highlight. The water is calm, clear, and perfect for toddlers to splash and play safely. Most resorts also have beautiful, easy-to-access pools for little ones.
Rosewood Beach Club – If you’re staying at Rosewood, this alone is a full day. Beachfront setup, calm water, and easy service makes it effortless with kids.
Explore St. George’s – A UNESCO World Heritage town filled with colorful buildings, cobblestone streets, and little squares to wander. Easy to explore with a stroller or carrier.
Hamilton strolls – The capital is small, walkable, and full of shops, cafés, and harbor views. Great for a slow morning outing with kids.
Crystal & Fantasy Caves – A fun, short adventure if you want something different. Kids love the dramatic cave formations and underground pools.
Scenic drives + lighthouse stops – Bermuda is tiny, so it’s easy to drive around and stop at lookout points, beaches, and the famous Gibbs Hill Lighthouse.
Where to Stay with a Toddler in Bermuda
- Rosewood Bermuda – My absolute top pick. Beautiful, peaceful, and incredibly family-friendly with amazing service and thoughtful amenities for kids.
- The St. Regis Bermuda Resort – Located on a gorgeous stretch of beach. Very luxe, slightly more affordable than Rosewood, and great for families.
- Hamilton Princess & Beach Club – The iconic pink hotel in Bermuda. Super fun, central location, and a great option for families who want to explore more of the island.
I can get your great VIP perks like upgrades, free breakfast and $100 hotel credit at any of these hotels. Just contact me here to inquire.
11. Mexico
We’ve been to Mexico several times—Cabo, Tulum, and Mexico City—and it’s such a great destination for families. It’s easy to reach from the U.S., which makes it perfect for a first international trip with a toddler.
We love how laid-back and welcoming it feels, and the food is a big plus. Our toddler is all about beans, quesadillas, and veggies, so mealtime will be a breeze for even picky eaters.
For a beach vacation, I’d choose Cabo. It’s super accessible, safe, and full of stunning resorts with beautiful beaches.
When to Visit Mexico with a Toddler
Late fall through spring is the best time to visit Mexico, especially if you’re headed to Cabo. You’ll get sunny skies, warm temps, and minimal rain—ideal for beach and pool time with little ones.
We like avoiding the summer months when it’s hot and humid, especially with a toddler in tow.
Where to Stay in Mexico with a Toddler
- Waldorf Astoria Los Cabos Pedregal – This resort is tucked away and peaceful, with amazing service and ocean views. They’re great with kids and offer spacious rooms with private plunge pools.
- Esperanza, Auberge Resorts Collection – One of our favorites. It’s beautiful, intimate, and very family friendly. They offer babysitting, kid-friendly meals, and have a calm beachy vibe that’s great for little ones.
Things to Do for Kids in Mexico
- Beach Time – The beaches in Cabo are stunning. Some aren’t swimmable due to strong currents, but many resorts have calm areas and amazing pools where toddlers can splash and play safely.
- Resort Activities – Many luxury resorts in Cabo offer kid programming, toddler-friendly pool areas, and wide open spaces to explore and play.
- Stroll + Snack – Enjoy slow mornings walking the resort grounds, sipping coffee, and letting your toddler explore. Local taquerias and cafes are casual and welcoming to families.
- Day Trip to San José del Cabo – A charming town with colorful streets and art galleries. It’s stroller-friendly and fun to explore in the early morning or late afternoon before nap time.
12. French Riviera
Our friends took their two toddlers to the French Riviera in May and had the most amazing trip. We were so jealous hearing about it that now it’s at the top of our family travel list!
They loved the pace of life there, the charming towns, and how toddler-friendly it all felt. Their favorite stops were Aix-en-Provence (so walkable and full of fountains!) and Èze, a hilltop village with unreal views. You could even combine it with a 3-day stop in Paris to make it extra special.
When to Visit France with a Toddler
May, June, and September are ideal for visiting the French Riviera. You’ll have perfect weather for strolling through towns, playing at the beach, and enjoying long outdoor lunches without the summer crowds or heat.
We’d skip July and August if possible—too hot and too busy for toddlers.
Where to Stay in French Riviera with a Toddler
With little kids, we always recommend choosing a home base and taking day trips. You can also split your time between two hotels max, but moving too much gets exhausting with little ones and all their gear!
- Grand-Hôtel du Cap-Ferrat, A Four Seasons Hotel – This is the dream. Lush gardens, a stunning pool, and top-notch service that welcomes families.
- Cheval Blanc St-Tropez – This one is elegant but totally family-friendly. Right on the water, with a quiet setting and kid amenities that make a big difference.
Things to Do for Kids in French Riviera
- Beach Days – Let your toddler run around in the sand or splash at the shore. The water is calm in many areas, and beaches like Paloma Beach in Saint-Jean-Cap-Ferrat are stroller-accessible.
- Markets + Cafés – The Provençal markets are colorful and fun for kids to explore. Grab fresh fruit, a baguette, and take snack breaks in the shade.
- Strolls Through Old Towns – Towns like Aix, Èze, and Antibes are full of cobblestone charm and pedestrian streets—perfect for stroller walks and toddler wandering.
- Scenic Train Ride or Car Day Trips – Explore nearby towns like Nice, Villefranche-sur-Mer, or Saint-Paul-de-Vence at a slow, flexible pace.
13. Portugal
Portugal is high on our family travel bucket list. I’ve heard it’s sooo family friendly—like, people let you cut the line if you’re carrying a baby. Italy felt a bit like this too (especially at the airport!), but apparently Portugal takes it to another level.
When we go, we’ll probably split our time between a beach spot, a city, and a little countryside. That way, everyone gets a bit of what they love – toddlers included!
When to Visit Portugal with a Toddler
Late spring (May/early June) or early fall (September) are ideal. You’ll get great weather without the scorching heat or crowds of peak summer.
Where to Stay in Portugal with a Toddler
- Algarve – For beaches, this is the spot. Look at Vila Vita Parc or Conrad Algarve—both are known for being luxurious and family-friendly. They have pools, beach access, and space for little ones to run around.
- Lisbon or Porto – For city vibes, cobblestone strolls, and culture. Lisbon is hilly but has elevators and trams that help with a stroller.
- Douro Valley – Perfect if the grownups want some wine and scenic downtime. Six Senses Douro Valley is dreamy—and they welcome kids with open arms.
Things to Do for Kids in Portugal
- Explore the Beaches – Some of the best family-friendly beaches in the Algarve are Praia do Camilo, Praia da Marinha, and Praia de São Rafael. Calm waves, golden sand, and room to play = toddler paradise.
- Lisbon’s Trams + Oceanário – Toddlers love the bright yellow trams and Lisbon’s aquarium is one of the best in Europe!
- Castles + Tile-Hunting – Wander through São Jorge Castle in Lisbon or the colorful Palácio da Pena in Sintra. So fun to explore with little ones.
- River Cruises in Porto or Douro – Sit back and enjoy the views while your toddler takes a snack break.
- Local Bakeries – Grab a warm pastel de nata and let your toddler try a little custard. There’s something so sweet about bakery stops together.
14. Walt Disney World, Florida
I can’t talk about the best trips to take with a toddler and not mention Disney. It’s iconic and going with a toddler under 2? They get in for free! With park tickets nearing $200/day, that’s a huge savings and makes this age a great time to go.
The best part is you can take it slow and stick to the toddler-friendly rides, parades, and character meet-and-greets without feeling pressure to do everything.
I actually worked at Disney World as an intern and had the chance to take my toddler niece and nephew multiple times! Our whole family had the most magical trip getting to take it slow and see everything through their tiny eyes!
When to Visit Disney World with a Toddler
The most magical time to go is early December right after they put up the holiday décor (yes, it goes up the day after Halloween!). Everything feels festive and twinkly, but go when crowds are much lower right before school lets out for winter break – don’t get caught there Christmas week!
Halloween is also a fun time with adorable toddler costumes and themed events.
I’d just avoid school holidays like spring break and the hot summer months with a little one—it’s crowded and so hot
Where to Stay in Disney World with a Toddler
I highly recommend staying somewhere convenient and toddler-friendly.
- Four Seasons Orlando – Luxury, calm, and full of kid perks. There’s a lazy river, splash pad, character breakfasts, and a complimentary shuttle to the parks. I love that it’s not actually in the parks and a bit removed.
- Polynesian Village Resort – This one is nostalgic for me—I worked here as an intern! It’s such a fun spot with monorail access (so easy with a stroller), tropical vibes, and a great toddler-friendly pool.
- Grand Floridian – Elegant but welcoming to families. The location can’t be beat—you’re right on the monorail and steps from Magic Kingdom.
Things to Do for Toddlers at Disney World
Stick to the classics:
- Magic Kingdom rides like Dumbo, It’s a Small World, Winnie the Pooh, and Peter Pan’s Flight are toddler favorites.
- Animal Kingdom is also great with little ones—there’s a safari ride where you can spot giraffes and elephants, plus the Boneyard playground and animal trails.
- Don’t skip Disney Springs (formerly Downtown Disney). It’s free to enter and super stroller-friendly. There’s a carousel, splash pad, tons of kid-friendly dining, and even a giant LEGO store where toddlers can play.
- Watch the parades and character shows—toddlers love the music and energy.
- Take advantage of Baby Care Centers in each park—they’re amazing for diaper changes, feedings, and quiet breaks.
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Want help planning a trip with your little one?
I’m not just recommending these destinations from a travel advisor perspective. I travel with two young kids myself, so I know how much the little details matter when you’re traveling with a toddler or baby.
I can help you choose a destination and hotel that actually works for your family, then plan the rest of the trip around what will make your time away easier and more enjoyable.
Want to keep it simple? You can also self book your hotel through my travel advisor portal and still receive available perks like complimentary breakfast, upgrades and hotel credits. Because a better room with kids is always huge!
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The Wrap Up: Best Places to Travel with a Toddler
Traveling with a toddler doesn’t have to be stressful and in fact, it can be so much fun. From stroller-friendly cities to toddler-approved beaches and family-welcoming hotels, there are so many amazing destinations that make traveling with little ones not only doable, but truly enjoyable.
We’ve taken our daughter everywhere from Japan to Germany, and every trip has taught us something new about traveling as a family. Whether you’re looking for a cultural city break, a beach escape, or something in between, these are some of the best places to visit with a toddler based on our own experience (plus a few that are high on our list!).
If you’re wondering where to go next with your little one, this list is full of toddler friendly inspiration with tips on when to go, where to stay, and what to do with kids in each spot.
As a luxury travel advisor and mom of 2, I would be so glad to help make planning with littles a bit easier for you! Inquire below.
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