Where should you travel with kids this summer?
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Travel has always been central to my life and I built an entire career based on the premise that I wanted to see the world. So when we decided to start trying, a slow sort of grieving crept in for all the places I hadn’t yet seen.
My husband helped snap me out of the mourning spiral with two reminders: I could still travel—maybe less, but not never—and eventually, we could travel with the baby.
That second part felt strangely radical. I had never considered that both could coexist. But I’m learning that traveling after kids is really a preference thing. Some parents prefer staying put while others crave a break from the monotony: the leaky faucet, the same park down the block. It’s a logistical headache, sure, but one that could also be quite manageable.
Which leads to the follow-up question: where? It’s not like I can scroll through my old Instagram bookmarks of chic, remote hotels and just… go. And Googling “family-friendly vacation” pulls up the same tired list (no shade to Disney but my son is far too young to appreciate a human-sized Mickey Mouse).
This doc is meant to fill that gap — it’s a living, growing list of real places that work with kids in tow. Add your own recs, use the filters, pass it along. Whether you’re deep in newborn life or traveling with toddlers, there’s room for you here.
Explore the full guide or scroll down for a few standout picks. More StickySheets to come.
Tyler Place Family Resort – Highgate Springs, Vermont
Why it works: Like summer camp, but everyone sleeps in a real bed.
Set on 165 lakefront acres, Tyler Place is the kind of place that lets your kid go full free-range without you needing to hover. It has biking, kayaking, crafts, and even childcare that runs all day so parents can actually… be on vacation? Think Dirty Dancing if it were rewritten for 2025.
Price: $$
Childcare: Full-day programs by age group
Palm Heights – Grand Cayman, Cayman Islands
With a dreamy beachfront and a low-key glam energy, Palm Heights feels grown-up without being uptight. There’s babysitting available with two days' notice (around $18/hour), and the hotel’s suites are ideal for families traveling together or needing a bit more space. Bonus: direct JetBlue flights from NYC.
Price: $$$
Childcare: Babysitting with notice (+ taxi/after-hours fee)
River Street Inn – Savannah, Georgia
Set along Savannah’s iconic riverfront, this inn puts you right in the middle of markets and squares, great for curious kids and stroller naps. (Savannah in general is a walkable city that has charm on every corner so you won’t have to coordinate car seats.) There’s no childcare, but the city’s pace makes it ideal for families who don’t need constant programming.
Price: $
Childcare: No formal childcare, but family-friendly vibe and walkability
Maslina Resort – Hvar, Croatia
Located in one of Croatia’s sunniest spots, Maslina is a design-forward resort with enough thoughtful touches (kids' programming, babysitting services, nature walks) to make it family-friendly without screaming family. It’s calm, elevated, and indulgent.
Price: $$$
Childcare: Babysitting available
Embassy Suites by Hilton – Orlando, Florida
If you’re heading to Disney but don’t want to spend $900 a night or sleep in a cartoon-themed room, this is your move. Embassy Suites gives you space, free breakfast (a parenting win), and is close enough to everything without being in it. Great for older toddlers and kids starting to ask about Mickey.
Price: $
Childcare: No formal childcare, but family-focused setup
Le Jardin des Douars – Essaouira, Morocco
This Moroccan stay is charming and relaxed, with lush gardens, hammams, and colorful rooms that don’t feel sterile. It’s very child-friendly (there’s a kids’ pool!) but has enough adult polish to make the trip feel like a getaway for you, too. The town of Essaouira is walkable and full of small adventures: markets, beach time, and camel sightings.
Price: $$
Childcare: Very kid-friendly, with a family focus
The St. Regis Longboat Key Resort – Longboat Key, FL
This newly opened resort is sleek, breezy, and right on the Gulf Coast — meaning soft sand, low waves, and a slower pace. It has kids’ programming, onsite babysitting, and a spa worth booking twice. It’s an ideal in-between for parents who want rest and access to sippy cups.
Price: $$$
Childcare: Yes, plus kids’ programming
Sublime Comporta – Comporta, Portugal
A few hours south of Lisbon, Comporta is often called the Hamptons of Portugal — and Sublime lives up to the name. It’s surrounded by pine forests, beaches, and rice fields, and it’s exceptionally kid-friendly without trying too hard. You can bike to the beach, nap by the pool, and end the day with local wine and early bedtime routines.
Price: $$$
Childcare: Child-friendly, though formal babysitting may need to be arranged in advance
Round Hill Hotel – Montego Bay, Jamaica
Round Hill is that rare blend of historic and relaxed. Ralph Lauren-designed villas, ocean views, and spa treatments for you with plenty of space for kids to roam. They’ll help arrange nannies (private or via the hotel), and the beach is shallow, warm, and toddler-friendly.
Price: $$$
Childcare: Nanny recommendations available