Multigenerational vacations are becoming increasingly popular with families, and the Caribbean islands are some of the best destinations for a getaway of this type. Planning a trip that appeals to everyone from a preschooler to a teenager to a grandparent can be challenging, but the quality time and bonding that happens on a multigenerational vacation makes it all worth it. The following destinations have activities and amenities that appeal to travelers of all ages!
Best Multigenerational Vacation Spots in the Caribbean
1. Puerto Rico
Puerto Rico truly has something for everyone—adult culture and history buffs love exploring Old San Juan and the Castillo San Felipe del Morro (from the 1500s!), while kids are enthralled by the island’s natural phenomena, including several bioluminescent bays. Puerto Rico also complies with the American Disability Act—helping to ensure that mobility-impaired visitors feel comfortable getting around.
Best time to visit: Try visiting in late spring to escape wintertime crowds. Find a rental in Puerto Rico!
Aruba’s year-round beautiful weather combined with its miles and miles of postcard-perfect white sand beaches make it an ideal vacation destination for beach-lovers of any age. Teens love the many adventure activities available, including diving, horseback riding, and wind sports like parasailing. Older guests enjoy boating and relaxing on the beach with a drink in hand.
Best time to visit: Any time! Find a rental in Aruba!
The island of Barbados offers multigenerational groups the perfect combination of beaches and opportunities for inland exploration (visit the Barbados Wildlife Reserve for a chance to see green monkeys and Cuban rock iguanas!). Viewed as one of the most accessible islands in the Caribbean due to campaigns like “Fully Accessible Barbados,” the family-friendly country ensures that all visitors feel safe and ready to relax.
Best time to visit: Visit from January to June to avoid the rainy season. Find a rental in Barbados!
4. St. Lucia
St. Lucia is a nature-loving family’s paradise—hiking opportunities at the Pitons (mountainous volcanic plugs) and the botanic gardens offer the whole group a chance to reconnect with the outdoors. Don’t miss Sulphur Springs—the drive-in volcano and mud baths are must-do activities for the whole family.
Best time to visit: Book a late spring vacation for off-season deals. Find a rental in St. Lucia!
As one of the safest and most family-friendly destinations in the Caribbean, Turks and Caicos is well-regarded by travelers of all ages. Kids will want to check out Provo Ponies for horseback riding on the beach (and in the water!) along with Little Water Cay to get up close and personal with iguanas. Several golf courses and plentiful spas offer adults a chance for some fun of their own.
Best time to visit: Visit in winter for the ultimate cold-weather escape. Find a rental in Turks and Caicos!
6. Castaway Cay
Castaway Cay is Disney’s private island in the Bahamas that is accessible solely by cruise. If your family enjoys going to the Disney parks, Castaway Cay is right up your alley. Port excursions to themed play areas and sea creature encounters appeal to little ones, while parents and grandparents appreciate watching the kids enjoy the magic and taking time to relax on the adults-only beach.
Best time to visit: The island is only accessible on a Disney cruise. Find a rental in Castaway Cay!
Unique opportunities for fun (like deep-sea fishing!) combined with history and natural beauty are what keep drawing visitors back to St. Kitts. The island’s Georgian architecture provides a beautiful backdrop to the island’s natural history, which the whole family can see on the St. Kitts Scenic Railway.
Best time to visit: Visit in summer, when room availability is high and prices are low. Find a rental in St. Kitts!
Jamaica is one of the best places to go for multigenerational groups with kids to expose them to a different (and extremely family-friendly) culture for a relatively affordable price. Whether your group consists of adventurers (try hiking the Blue Mountains or going white water river rafting) or a more relaxed crowd (try one of the meditation centers or many hotel spas), Jamaica is sure to have something to please every one of your fellow travelers.
Best time to visit: Book a trip for late fall for great deals on accommodation. Find a rental in Jamaica!
This article was written by Kaitlyn Lannan