everywhere we traveled with a baby : Our Favorite Places to Travel with Kids Under 2
Yes, We Took a Baby to 10+ Destinations—and Lived to Tell the Tale!
Traveling with little ones under two might sound like a logistical nightmare, but for our family, it became one of the most beautiful (and often hilarious) chapters of our travel story.
Between diapers in airports, strollers on cobblestone streets, and countless naps on the go, we’ve discovered that travel with a baby doesn’t have to stop—it just looks a little different.
before their second birthday, we took over 10 different trips and each brought something special. But a few rose to the top as our absolute favorites—for their ease, beauty, and how perfectly they paired with the pace of family life.
✨ Our Favorite Baby-Friendly Destinations
Tuscany, Italy
Slow days, sunny vineyards, and sleepy hilltop towns—Tuscany was made for traveling with a baby. We’d explore one village in the morning, have a long, delicious lunch, and then head back for naptime while the adults sipped wine by the pool or booked a spa treatment. Slow travel is the name of the game—and it fits baby's schedule perfectly.
a few alternatives :
Napa Valley
Douro Valley, Portugal
Loire Valley, France
London + The English Countryside (Cotswolds)
London always feels doable with a stroller and plenty of green parks, but pairing it with the Cotswolds gave us the best of both worlds. Think countryside strolls, cozy pub lunches, and charming villages that welcome families with open arms. Easy to navigate and full of charm!
a few alternatives :
Paris + the countryside (loire, Bordeaux, and Alsace are some of our favorites)
Boston + nantucket or martha’s vineyard
mexico city + san miguel de allende
Turks and Caicos
The easiest Caribbean island we’ve visited with a baby! Direct flights, calm beaches, and short distances make Turks and Caicos feel so doable with little ones. Grace Bay is especially family-friendly—perfect for wading in the shallows, beach naps, and evening strolls by the sea.
a few alternatives :
anguilla
st lucia
jamaica
Sailing by Catamaran
Okay, hear us out. We took a 2-year-old and a crawling 9-month-old on a sailing trip... and it was incredible. With extra hands from grandparents and a non-walking baby, the catamaran felt like a floating haven. Life was simple—sun, sea, naps, and sunsets. (We highly recommend this if you're brave or have backup!)
our travel list with a baby:
NYC - great at any age honestly, as long as your kids will ride in a stroller! I took our 4 year old over the holidays to see the Rockettes + holiday decorations and we loved it.
Key West - we loved the drive from Miami - so scenic. we prioritized staying somewhere with a great beach - not the case everywhere in the keys. we stayed at Casa Marina in KW and Baker's Cay in Key Largo -both excellent choices for families.
London - we always love London and our kids go at least once a year - so we know all the tea on what to do at every age. Our favorite age so far has been 4+5 because we did ALL the things and ALL the tours. Such a great age to be tourist in this city!
Barcelona - we had a great time here with a 5 month old! Baby wearing was clutch! We enjoyed nice dinners and rooftop sunset drinks.
Charleston + SAVANNAH - this is a perfect city for small ones - easy to walk around plus the beach is SO close. We love the food scene in Charleston so it's a perfect place to start dining out with kids and getting them used to eating in restaurants.
Greece by catamaran - we were a little crazy with this one, we had a 2 yr old and 9 month old on board. But we had grandparents for extra hands! Our youngest wasn't walking - just slowly crawling so I think this is a great age to sail - especially with one kid! We love being on a boat and being able to see a lot and only unpack once!
Big Sky - what a beautiful place! We went in summer and enjoyed long hikes (wearing the babies!) and a day trip to Yellowstone. We really had a great time but would also love this trip as the kids were a bit older - 5+ would be so fun so they could hike and enjoy some of the outdoor activities on their own!
Turks and Caicos - truly so many Caribbean islands would check the box of a perfect first trip with a baby! We loved Turks because we had a direct flight and you can get around the island so easily - making the travel process so much easier with a baby. The beaches here are stunning and calm!
Belize - one of my favorite trips and I can't wait to go back! We stayed on ambergris Caye and loved it but it was a big travel day for us. You have to fly into Belize City and then take a hopper flight here - our kids were champs but I do think this is great trip for 5+. Also, there is SO much more to Belize - our favorite trip for clients is a split stay between the jungle and the coast. We recommend this for 6+ so the kids can zip line and fully participate. We can't wait to go back once they are bigger!
Tuscany - traveling with a baby is all about embracing some of the slow experiences. Set yourself up with one activity per day max and allow the time to relax and rest together as a family without the distractions of home. Tuscany couldn't be a more perfect place to do this! Small villages make for a perfect midday activity to explore and have lunch. Head back for an afternoon nap - maybe the grown ups dip in the pool, hit the spa, or relax with a good book. It is all about slow living here and you'll fit right in with baby's schedule!
🧳 Our Baby Travel Tips:
One activity a day is plenty. Embrace the slow rhythm of baby travel.
Always pack a baby carrier AND a stroller. You'll use both!
Choose destinations with short travel times or easy connections.
Find hotels with cribs, kid amenities, and included breakfast—it makes mornings smoother. use a travel advisor that specializes in family travel!
Be flexible. The best memories often happen when you least expect them.
Ready to start your own adventures with your sweet little one? Whether it’s Europe, the Caribbean, or a road trip close to home—traveling with a baby is the perfect way to make family memories.
We promise: it’s totally worth it. 💛
Would you like help planning your next baby-friendly getaway? I can help you find the best flights, stroller-friendly hotels, and itineraries that work with naps, feeding, and fun.
