The Best Places to Travel with Your Grandkids
There’s something magical about traveling with multiple generations. Some of my favorite memories have been on vacations with my parents right alongside my kids, watching them build sandcastles with their grandparents, seeing a new place through their eyes, and soaking up the kind of slow, unhurried, memories and time together that a normal week at home never allows.
These multi-generational trips, where we bring my mom and dad or my husband’s parents along, have quietly become my favorite kind of family travel. We get to be together, the grandparents get real quality time and build a real bond with the kids, and the parents get a genuine break with a few extra sets of hands around. It’s a win-win for everybody.
Whether you’re a grandparent who wants to spoil the grandkids somewhere really special, or a parent planning a vacation where toddlers and grandparents are equally happy, these are the destinations I recommend again and again.
From easy beach escapes to bucket-list adventures, here are my top picks for the best places to travel with your grandkids.
(don’t forget to get matching outfits for your trip from here!)
One quick thing before we get into it. I plan a lot of these multi-generational trips for clients, and because I’m a Virtuoso travel advisor, I can layer real perks onto most of the hotels below: complimentary breakfast for the whole crew, resort or spa credits (often 100 dollars or more), room upgrades when they’re available, early check-in and late checkout when the hotel can swing it, and VIP treatment the moment you arrive. It’s the same rate you’d pay booking direct, just with the extras. I’ll drop my booking portal under each destination, and the password is always JETSETTERS.
Hawaii – The Ultimate Multi-Generational Paradise
Hawaii is my go-to when I want everyone happy on the same trip. Maui, Oahu, Kauai, the Big Island, it almost doesn’t matter which one you pick, the pace is easy and the aloha is real. Grandparents get slow mornings and sunset mai tais, the kids get beaches and waterslides, and nobody needs a passport.
Why It’s Great for Grandparents & Grandkids:
You get relaxation and real adventure in the same day, stunning beaches in the morning and a volcano hike in the afternoon, resorts built for kids with waterslides, lazy rivers, and legit kids’ clubs that still pamper the grown-ups, and it’s an easy domestic trip with no passports required.
Grandkid-approved activities: Snorkeling in Maui’s Molokini Crater, visiting the Honolulu Zoo, or experiencing a traditional luau together.
Where to Stay:
Four Seasons Resort Maui at Wailea is the one we keep going back to. We’ve done it twice with my parents along, and it’s the rare hotel where the kids and the grandparents are equally happy the whole week. Read my full Four Seasons Maui review here
Grand Wailea is a little more dated, but the kids could not care less. It has a canyon of waterslides, a water elevator, and a lazy river that will keep them busy from breakfast to sunset.
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Ready to book Hawaii? Book it through my travel portal here (password: JETSETTERS) for my Virtuoso perks: complimentary breakfast, a resort credit, room upgrades and early or late checkout when available, and VIP status on arrival. Prefer I handle the details? Fill out my trip inquiry form here.
Los Cabos, Mexico – A Luxe Escape for the Whole Family
Los Cabos is that easy blend of grown-up luxury and kid adventure, and it’s a short nonstop from a lot of US cities, which matters a lot when you’re getting grandparents and toddlers onto the same flight. You’ve got whale watching and boat rides out to the Arch, world-class golf, spas for days, and resorts that actually know how to keep every generation busy.
Why It’s Perfect:
Luxury resorts with the kind of service that spoils the grandparents, short direct flights from the US, and enough variety that a pool day, a whale-watching morning, and a golf afternoon can all happen on the same trip.
Grandkid-approved activities:
- Boat ride to El Arco and whale watch or go snorkeling!
- Day trip to Todos Santos for a colorful Mexican village experience.
- Pool days + kids’ club magic while grandparents enjoy the spa!
Where to Stay:
Waldorf Astoria Los Cabos Pedregal is family-friendly luxury with an incredible kids pool, and we have stayed here multiple times with the grandparents.
My other top pick, and maybe the best of the bunch if actually swimming matters to you, is Auberge Chileno Bay Resort & Residences. Most Cabo beaches have rough surf you can’t swim in, but Chileno fronts one of the only genuinely swimmable, snorkel-friendly bays on the corridor, and it’s Blue Flag certified. There’s a three-tier infinity pool with a dedicated family pool and a shallow kids’ pool, a kids’ club for the little ones (roughly ages 5 to 12) and a teens’ club for the older crew, plus multi-bedroom villas and Sky Villas with full kitchens that are ideal when you want the whole family under one roof.
I get you VIP perks at either hotel (Free daily breakfast, $100 resort credits, room upgrades and more!) just reach out here to plan your trip – as a top travel advisor, I don’t charge anything to book hotels, just perks for you!!
Rent a Villa in Cabo
Renting a villa in Cabo is a great call for a group. You’re all under one roof, you save on rooms and on eating out, and you can bring in a private chef. My go-to chef and bartending crew is Spicy Gourmet Los Cabos, and their food and cocktails are some of the best I’ve had in Cabo. It beats packing the whole group up for every meal out. Tell them Jetset Christina sent you.
Maison Mantea Villas
If you’re traveling with a group and looking for an insanely luxurious house to rent in Pedregal, you can read more about this place here, but it is hands down the most beautiful place I’ve been in Mexico. This villa is 7 star, and located in the exclusive, safe, gated community of Pedregal.
Ready to book Los Cabos? Book it through my travel portal here (password: JETSETTERS) for my Virtuoso perks: complimentary breakfast, a resort credit, room upgrades and early or late checkout when available, and VIP status on arrival. Prefer I handle the details? Fill out my trip inquiry form here.
Italy – Because Every Kid Deserves to Eat Pasta in a Piazza
If you’re up for an international adventure, Italy is one of my favorite places to take the grandkids. History, culture, food, and the kind of shared wonder that hits kids and grandparents equally.
Why It’s Perfect:
No one is too old or too young for pizza and gelato, the history actually comes alive for kids when they’re standing inside it, and the trains make it easy to hop between cities without anyone getting behind a wheel.
Grandkid-approved activities:
- Rome: The Colosseum, throwing coins into the Trevi Fountain, eating all the pizza.
- Florence: Climbing the Duomo, a fun Vespa sidecar tour (for older kids!).
- Tuscany: Relax in a Tuscan villa all together, spending your days doing cooking classes, and swimming in the pool!
- Venice: Riding gondolas, feeding pigeons in St. Mark’s Square.
Where to Stay:
For a multi-gen group I almost always base everyone in a villa in Tuscany, one big house with a pool and a kitchen made for family cooking classes, with a few nights in Rome on either end. My full guides to Rome, Tuscany, the Amalfi Coast, and Venice have my specific hotel picks for wherever you’re headed.
Dreaming of Italy? Book it through my travel portal here (password: JETSETTERS) for my Virtuoso perks: complimentary breakfast, a resort credit, room upgrades and early or late checkout when available, and VIP status on arrival. Prefer I handle the details? Fill out my trip inquiry form here.
Charleston, SC – Southern Charm & Beach Bliss
If you’d rather stay stateside, Charleston is made for a multi-generational trip. Southern hospitality, real history, easy beach days, and some of the best food in the country, all in one walkable, charming place.
Why It’s Perfect:
The downtown is walkable and genuinely charming, the beaches are beautiful and calm, and there’s a great mix of kid activities, shopping, and a serious dining scene for the adults.
Grandkid-approved activities:
- Exploring the historic streets in a horse-drawn carriage.
- Visiting the South Carolina Aquarium (our favorite!)
- See the Pineapple Fountain at Waterfront park (you can even wade in it in the summer!)
- Beach days on Isle of Palms, Sullivan’s, or Kiawah Island.
- Ice cream at Beardcats on Sullivans – our fav!
- Dinner at any of these top best restaurants with kids in Charleston
Where to Stay:
Wild Dunes Resort is the easy family pick, very kid-friendly with fun pools and right on the beach, great for all ages.
The Sanctuary at Kiawah Island is the more traditional, polished luxury option, beautiful and right on the beach.
Charleston Place is where you stay if you want to be right downtown in the middle of it all.
Rent a house on the beach!
I always think renting a house is a great move for a multi-generational trip given you’d be paying for so many hotel rooms, so it makes more sense to all be in one house! Plus, you can cook breakfasts and lunches at home, or even hire a private chef! Reach out to me here and I’ll help with the perfect one for your stay.
Recently Renovated Luxury Oceanfront Group House in Isle of Palms
Oceanfront Isle of Palms with Fire Pit, Amazing Views
Planning a Charleston trip? Book it through my travel portal here (password: JETSETTERS) for my Virtuoso perks: complimentary breakfast, a resort credit, room upgrades and early or late checkout when available, and VIP status on arrival. Prefer I handle the details? Fill out my trip inquiry form here.
Mayakoba, Mexico – The Quiet, Grown-Up Side of the Riviera Maya
On Mexico’s Riviera Maya, Mayakoba trades the Cancun crowds for something calmer and more grown-up, a gated enclave of world-class resorts laced with lagoons and mangroves, built for both relaxing and getting out into nature.
Why It’s Perfect:
It’s luxe but low-key with none of the wild Cabo party scene, there’s real nature for the kids like cenotes, snorkeling, and eco boat rides through the lagoons, and the resorts are genuinely built for families.
Where to Stay:
Rosewood Mayakoba is the ultimate splurge, all private plunge pools and lagoon suites.
Fairmont Mayakoba is the more affordable pick and the more family-forward of the two, with a great kids club and pools.
I get you VIP perks at either hotel (Free daily breakfast, $100 resort credits, room upgrades and more!) just reach out here to plan your trip – as a top travel advisor, I don’t charge anything to book hotels, just perks for you!!
Ready to book Mayakoba? Book it through my travel portal here (password: JETSETTERS) for my Virtuoso perks: complimentary breakfast, a resort credit, room upgrades and early or late checkout when available, and VIP status on arrival. Prefer I handle the details? Fill out my trip inquiry form here.
Harbour Island, Bahamas – Palm-Beach-meets-Nantucket Vibes in the Bahamas, Laid-Back Luxury
If you want a chic little island escape without the crowds, Harbour Island is a dream. Some of the most beautiful pink-sand beaches you’ll ever see, golf carts as the main way to get around, and a laid-back but polished Caribbean feel.
Why It’s Perfect:
It’s small, safe, and easy to get around by golf cart, the water is calm and shallow for little swimmers, and the whole island has a laid-back, no-mega-resort charm.
Where to Stay:
The Dunmore is the boutique pick, a preppy pink-and-white, cottage-style hideaway set right above Pink Sands Beach. It’s small and clubby in the best way, the kind of place the whole family settles into fast, and the food is genuinely excellent.
If you’re a bigger group, the island also has some spectacular villas to rent, several with pools and just steps from the pink sand. Reach out to me and I can help find the perfect one for you.
This Ultra-Luxury Oceanfront Villa with Pool
Photo courtesy of their VRBO page
Just steps from the Pink Sands beach, this ultra sleek and modern villa is a vacation paradise! Complete with a 55 ft. pool, a gym, a theater, spacious outdoor living areas, and a chef-ready kitchen. Includes 8 spacious rooms and a master suite perfect for large group or families. The amazing view in the garden and pool area is great for evenings when you want to dine al fresco under the stars! This is where you go for the best luxury villa on Harbour Island.
The Beacon Hill Estate
If you want your very own secluded paradise surrounded by lush palms, for that ultimate privacy, then the ultra ultra luxurious villa on Harbour Island the Beacon Hill Estate is for you. With direct beach access and a layout that encourages indoor-outdoor living, the best trip ever is guaranteed.
Photos courtesy of their VRBO page
Sunnyside Villa
Photo courtesy of their VRBO page
Dreaming of Harbour Island? Book it through my travel portal here (password: JETSETTERS) for my Virtuoso perks: complimentary breakfast, a resort credit, room upgrades and early or late checkout when available, and VIP status on arrival. Prefer I handle the details? Fill out my trip inquiry form here.
Anguilla – The Caribbean’s Best-Kept Secret
Anguilla is one of my all-time favorite Caribbean islands. The beaches are the whole point here, Shoal Bay East is the famous one, long and powder-soft, and the water stays calm and shallow far enough out that the grandparents can wade in with the little ones. Add in some of the best food in the Caribbean and a welcoming, unpretentious pace, and it’s an easy island to bring every generation to.
Why It’s Perfect:
World-class beaches without the crowds or the pretense, a calm and safe pace that suits every age, and a food scene that punches way above the island’s size.
Where to Stay:
Malliouhana, Auberge Resorts Collection is the pick for boutique island chic.
Four Seasons Anguilla is your full-service luxury beachfront option, and it’s great with kids.
I get you VIP perks at either hotel (Free daily breakfast, $100 resort credits, room upgrades and more!) just reach out here to plan your trip – as a top travel advisor, I don’t charge anything to book hotels, just perks for you!!
Ready for Anguilla? Book it through my travel portal here (password: JETSETTERS) for my Virtuoso perks: complimentary breakfast, a resort credit, room upgrades and early or late checkout when available, and VIP status on arrival. Prefer I handle the details? Fill out my trip inquiry form here.
Jamaica – Round Hill, Where Grandkids and Grandparents Both Feel at Home
If you want one property that genuinely works for a three-generation trip, put Round Hill Hotel and Villas near the top of the list. It sits on a private peninsula just west of Montego Bay, and it’s the rare place that feels equally right for honeymooners and for a big family that booked a villa with the grandparents. It’s old-world Jamaican elegance with zero mega-resort energy.
You can stay in the Pineapple House, the hotel wing Ralph Lauren designed himself (he’s a longtime homeowner here), or take one of the 27 private villas, most with their own pool and villa staff who will cook your breakfast and help with the kids. There’s a Pineapple Kids Club for the little ones, water sports, tennis, and pickleball off the beach, and a hillside spa set in a restored great house for when the grandparents want an afternoon to themselves.
Want to book Round Hill? Book it through my travel portal here (password: JETSETTERS) for my Virtuoso perks: complimentary breakfast, a resort credit, room upgrades and early or late checkout when available, and VIP status on arrival. Prefer I handle the details? Fill out my trip inquiry form here.
Cruising – The Easiest Multi-Gen Trip You’ll Ever Plan
Cruising for a multi-generational group it’s tough to beat. You unpack once, everyone from a two-year-old to an 70-year-old has something to do, the grandparents can slip off to a quiet adults-only deck while the kids are at the club, and dinner is handled every single night. A few lines I’d look at, depending on your crew:
Explora Journeys is my pick for families who want the polish of a small luxury ship without the crowds. There’s a kids’ and teens’ club, connecting suites built for multi-gen groups, and a serene adults-only pool for the grandparents. The newest ships have the most expanded kids’ facilities, so it’s worth checking which ship your sailing uses.
Disney Cruise Line is still the gold standard when the grandkids want the full Disney magic, with smartly designed connecting staterooms, age-tiered kids’ clubs, incredible shows, and adults-only restaurants and lounges so the grown-ups get real downtime too.
Royal Caribbean is the best big-ship value when you’re trying to please toddlers, teens, and grandparents all at once. The newest ships pack in water parks, surf simulators, ziplines, ice skating, and family suites that sleep the whole group.
One heads-up: cruise-line kids’-club ages, ship deployments, and pricing change constantly, so I always confirm the exact details for your ship and sail date when we book.
Want help booking a cruise? I book cruises too, often with onboard credit and extra amenities to sweeten the sailing. Reach out through my travel portal here (password: JETSETTERS) or fill out my trip inquiry form here.
Where Will You Go Next with Your Grandkids?
A multi-generational trip is one of the best ways to slow down and actually be together, and the extra hands with the kids mean the parents get a real break too. Beach, culture, or a mix of both, every place on this list is grandkid-approved and grandparent-approved.
Ready to plan yours? As a luxury travel advisor I can secure VIP perks at most of these hotels: complimentary breakfast, 100 dollar resort credits, complimentary room upgrades when available, VIP recognition on property, and early or late checkout when available.
Fill out this inquiry form here and I’ll help you plan your trip, or you can go directly to my travel portal and see my exclusive travel advisor rates and book yourself with all of my perks included! The password is always JETSETTERS (save this page to your bookmarks for future trips!)
Have you traveled with your grandkids before? Tell me your favorite spot in the comments.
