Snowbird Getaway: 5 Fabulous Multi-Gen Destinations in the Caribbean

Snowbird Getaways

Atlantis in Nassau, The Bahamas, is a tropical playground with something for every age group. Photo: The Atlantis Hotel/Jim Byers

The Caribbean has hundreds of great resorts. Here are some of my fave spots for families, plus a floating option.


A Floating Hotel

Photo: Courtesy of Oceana Cruise Lines

Caribbean cruises are an outstanding way to enjoy a multigenerational family holiday. My first cruise of any kind was in 2004, roughly five months after my mother suddenly passed away. She’d always talked about a family cruise, so my dad said, “Let’s do it.” Dad was in his early 70s, my wife and I and my sister were in our late 40s, with my niece in her mid-20’s and three teenagers. The kids slept in and ordered room service at no extra charge, and we met every day for swims or activities. Our teens hung out together and made regular treks to the Johnny Rocket’s burger place. Every night we met and exchanged notes about what we did during the day, and then planned the next one. We knew the kids were safe, and they could do what they wanted, while still spending time with their parents and grandfather. It was a trip we’ll never forget.


The Crane, Barbados

The Crane Resort, Barbados. Photo: Jim Byers


This is one of my favourite resorts in the Caribbean. It’s a beautiful property draped on top of a cliff on the southeast shore of the island, far from the major resorts but close enough to get what you need. There are large, spacious units for families (up to three bedrooms, many with private plunge pools), and plenty of open space on the grounds for kids to play. There’s a small village with a store selling the basics, as well as an ice cream shop. The beach, reached by an elevator or a set of stairs, is one of the finest in the Caribbean, with gleaming white sand and a rugged cliff. The on-site restaurants are outstanding, and the swimming pools go on forever. You’ll also find some historic buildings, as this is said to be the oldest resort on the island. Just a short walk away is Cutters restaurant, a casual place with terrific flying fish sandwiches, a rum punch that’s won a ton of awards and a friendly staff. Mick Jagger has been known to come in for a bite.

Half Moon Resort, Jamaica

Half Moon Resort, Jamaica. Photo: Jim Byers



An outstanding spot for the whole clan, with large villas and hotel rooms that give everyone space to spread out. Rose Hall Villas offers five-, six- and seven-bedroom accommodations, and are perfect for families, groups and golfers. Each villa features a living and dining room, outdoor living space and private pool, not to mention a butler, housekeeper, and a cook. The beach is terrific, and they offer everything from tennis to horseback rides in the surf (the horses love cooling off in the ocean). Look for fun pools for the kids and grandkids, and excellent food for the adults, including the fine Sugar Mill Restaurant. The Half Moon shopping village is right next door, and there’s also a golf course. Bonus: you’re only a short drive from the airport in Montego Bay.

Options in Anguilla

Aurora Resort, Anguilla. Photo: Jim Byers


On a budget? Shoal Bay Villas features casual studio and one- or two-bedroom apartments. Each is equipped with a full kitchen, air conditioning and a balcony or porch. There’s also a small pool, and you’re smack dab in the middle of Shoal Bay East, one of the top stretches of sand on an island that’s known for remarkable beaches. There’s a casual restaurant/bar called Elodia’s a few meters down the beach, which is ideal for families with little ones. Other resorts include the beautiful Aurora Anguilla Resort & Golf Club, formerly the CuisinArt, which has spacious junior suites available. There are plenty of villas to be had, as well. Anguilla is just a short boat ride from St. Maarten.

Atlantis, The Bahamas

Atlantis Hotel, Nassau. Photo: Jim Byers


If your family is bored here, you’ve got problems. Look for dolphin shows, endless pools, waterslides and more. Aquaventure at Atlantis is a 141-acre playground with something for every age group. There’s a lazy river but also a wild, rushing attraction called The Current, which whisks tube riders on powerful waves. The Leap of Faith slide features a sharp, 18-meter drop from a pseudo-Mayan temple into a clear, acrylic tunnel submerged in a shark-filled lagoon. The next-door Marina Village offers fun shops and casual dining places overlooking glittering yachts. Also great fun is a trip to the Blue Lagoon, less than a half-hour away by boat. You’ll pass homes that are said to be owned by the likes of Oprah Winfrey and Tiger Woods before being deposited on a beautiful island with beaches, a quiet lagoon for boating or swimming and a nice outdoor restaurant.

Editor’s Note: This story is meant to be inspiration for your travel planning — for whenever you’re comfortable cruising or travelling abroad. Keep an eye on Canada’s Travel Advisories for the latest pandemic guidelines. Currently, the Canadian government is advising to avoid all travel on cruise ships outside Canada due to COVID-19.