I’m floating above a coral reef, my gaze following a school of striped sergeant major fish, when my nine-year-old grandson glides past and points to his discovery—a spiny lobster the size of a small tricycle.

“Do you think Mom would let me use my souvenir money to go snorkelling again tomorrow?” he asks as we bob to the surface. 

“I’m sure she would,” I answer, thinking of the towering stack of plastic toys in their garage. 

Research has shown that choosing experiences over material goods can make you happier, so our conversation was quite a welcome surprise. When planning our Caribbean vacation, I’d expected to spend family time splashing in swimming pools together but hadn’t imagined sharing life lessons on a coral reef.

I’m not alone in discovering the unexpected joys of multi-generational travel. An increasing number of families are seeking experiences that bring siblings, parents and grandparents closer. Following are some ideas for multi-generational trips of a lifetime.  

Ireland: For history-loving families

With its vistas of windswept cliffs, rich history and strong tradition of storytelling, Ireland offers a fascinating backdrop for a variety of family pursuits. Begin in Dublin, where children under 12 travel free on the double-decker Dublin Bus Hop-on Hop-off tour. Among the 33 stops is Dublinia, where kids can soak up Viking history while learning alphabet runes. There’s just enough gruesomeness in the medieval Black Death diorama to keep teens riveted, while preschoolers will have potty-humour fun at the Viking-age bathroom display (moss toilet paper—ew!). Continue your Nordic immersion with a visit to the Viking Triangle in Waterford, Ireland’s oldest settlement (and a prime spot for adults to invest in some crystal family heirlooms). Then a drive through emerald countryside takes you past a variety of castles and ruins and up to the Cliffs of Moher, where watching surfers ride 12-metre-high waves on the Atlantic Ocean is an exhilarating thrill.   

Where to Stay 

Splurge Castles are scattered throughout Ireland, but, for families, Ashford Castle near Galway is extra-special. Built in 1228, its moats, stone walls and turreted towers make it appear as though it’s been lifted from the movie Frozen (but, thanks to a major refurbishment, it’s minus the drafty corridors). The grounds are also home to Ireland’s first School of Falconry and, during a Hawk Walk, families can fly a Harris’s hawk, letting it swoop through the ancient forest at 60 kilometres an hour to snatch food from suitably gloved fingers. 

Save The Croke Park Hotel’s location, 10 minutes north of the Dublin city centre, makes it perfect for families who want to visit the nearby Dublin Zoo, National Botanic Gardens or Croke Park stadium, which hosts Gaelic games like hurling. Kids will love amenities geared toward them, like teddy bears and pint-sized robes and slippers.

Anguilla: For families who want to mix beach time with local culture

From music and indigenous heritage to a lively cuisine scene, Anguilla—a short ferry ride from St. Martin—offers plenty of enriching experiences. Its 33 uncrowded white-sand beaches and warm Caribbean charm are added bonuses. Begin at The Amerindian Interpretation Centre and Trail, a new historic zone featuring interpretive trails, a straw hut, a subterranean cavern and 1,600-year-old artifacts of the island’s indigenous people on display in the reception area. On another day, head to The Dune Preserve, a funky seaside shack known for its barbecue and live music. Kids will enjoy exploring the eatery’s treehouse-style, driftwood construction, while adults can get a celebrity selfie with its owner, reggae legend Bankie Banx. 

Where to Stay 

Splurge A top family stay is the Viceroy Anguilla, located near crescent-shaped Meads Bay. While some suites come equipped with family-friendly amenities such as fridges, microwaves and kitchen gear, they certainly don’t sacrifice glam in their contemporary decor. The resort’s activity menu includes a kids’ club, rock-wall climbing and, for teens, the opportunity to make jump shots on a basketball court that’s a fave of visiting NBA stars. A sparkling infinity pool with zero-entry access (no stairs) is ideal for seniors and toddlers. Dining is helmed by esteemed Miami-born executive chef Rafael Gonzalez, who creates kids’ menus so delightful, they won’t even notice it’s healthy.

Save Everyone will feel at ease at the Anacaona Boutique Hotel situated at the Meads Bay beach. Relax in the pool or in a tropical garden hammock, then try snorkelling at the beach. Dine poolside at the family-friendly Firefly Restaurant among the chatter of tropical tree frogs, or grab a pie to go at Firefly’s AXA Pizza parlour.

Palm Springs: For nature lovers

Set against a backdrop of whisky-hued desert, starry skies and violet foothills, the Greater Palm Springs area (a string of nine desert cities) goes beyond the usual family destination in terms of wow factor. No matter if your entourage includes the stroller crowd or grandma and grandpa, it offers a winning mix of luxury accommodations, nostalgic modernist history and outdoor attractions. Check out the Living Desert Zoo in Palm Desert where the  new exhibit, Guardians of the Living Desert, injects some fun into education, offering pint-sized paleontologists the opportunity to dig for dinosaur fossils and teens the chance to take a selfie with a lifelike T. Rex. On another afternoon, go horseback riding through Palm Canyon where you might hear the beep-beep of roadrunners as they scurry along the rocky gorge.  

Where to Stay 

Splurge After full days of exploring the desert, look forward to cooling off at the Spanish colonial-style Omni Rancho Las Palmas Resort & Spa, the area’s only resort with its own water park. All ages will enjoy glimpses of the desert in full bloom while swooshing down Splashtopia’s waterslides, floating in the meandering lazy river or basking in a cliffside hot tub. Opt for a poolside room, and you can watch stars rise high in the sky from your own private patio. 

Save Introduce the kids to the Westin Mission Hills Golf Resort & Spa’s Director of Fun and you might never see them again. Located in the heart of Greater Palm Springs, the resort offers non-stop thrills with an arcade, a 60-foot waterslide and a Kid’s Club offering activities like wildlife encounters with reptiles and amphibians.

Peterborough & the Kawarthas, Ontario: For adrenalin-seeking adventurers  

Does your teen think the perfect vacation means shopping malls, video games and lots of battery life on their mobile devices? Then it’s time to pack the outdoor gear and head to Peterborough & the Kawarthas, a still-under-the-radar region just 90 minutes east of Toronto. Dotted with lakes, it offers enough excitement to entice even the most city-bound family. Go kite-boarding, float along the Trent-Severn Waterway or strap on some headlamps and go spelunking underground in the seven dripping Warsaw Caves. At the Canadian Canoe Museum, older kids can test their paddling skills by attempting to match the 50 to 60 paddle strokes per minute of a real voyageur, while the younger crowd can watch artisans showing off heritage skills like canoe-making and basket weaving. Parents and grandparents will enjoy reminiscing over Pierre Trudeau’s famous buckskin jacket and birchbark canoe.     

Where to Stay 

Splurge At Elmhirst’s Resort, a collection of cottages located on 100 hectares of waterfront, the family-pleasing menu of resort activities includes horseback riding, water-skiing, swimming and a full-service spa. Take a wagon ride led by the resort’s team of Clydesdale horses and you’ll learn about sustainable eco-initiatives such as naturalizing the Rice Lake shoreline, composting and raising the herd of black Angus cattle sourced for the dining room’s farm-to-table cuisine. 

Save All of Clearview Cottage Resort’s one-, two-, three- and four-bedroom cabins come with full kitchens, screened-in porches, barbecues, picnic tables and access to Clear Lake. The resort also has activities for all ages, including bass fishing, beach volleyball, tube rides, bonfires and an inflatable water park.