3 Tips for Planning the Best Family Vacation in the Caribbean

Family vacations require a lot of planning. Picking an appropriate destination is crucial, since these gatherings may be more successful — and fun — when they take place in a desirable, easy-to-reach place that multiple family members can enjoy. The Caribbean, with its scenic islands and short travel times from the North American continent, stands out for this very reason. 

But what’s the best way to plan a family reunion in this picturesque part of the world? 

Here, we break down some of the most important factors to consider and provide examples of noteworthy ways to craft a memorable family trip or reunion in the Caribbean. 

Book Hotels That Make It Easy 

Several hotels around the Caribbean offer packages and/or on-site assistance to make it easier to plan a family reunion. 

At Puerto Rico’s The St. Regis Bahia Beach Resort, for example, two staff members handle the planning details for reunions. 

In the Dominican Republic, the Exclusive Collection manager at Club Med Miches Playa Esmeralda can help arrange unique experiences such as private beachfront family dinners and private dinners in the La Perla suite or La Cava wine cellar. The property also offers eco-friendly family activities, including learning how to plant and compost ingredients in the hotel’s community garden. 

Among the hotel companies offering special perks for family reunions is Beaches Resorts, which includes a free group photo session for families who book five or more rooms, and a free group picnic, group dining and other activities for bookings of 10 or more rooms. 

Also piling on the perks is Coconut Bay Beach Resort & Spa in St. Lucia; for bookings of 10 or more rooms, benefits include private airport transfers and check-in for family members arriving on the same flight. 

Meanwhile, Bequia Beach Hotel, located in St. Vincent and the Grenadines, offers a Family Reunion Package that includes VIP transfers from the Bequia airport or ferry port, welcome drinks and canapes on arrival, daily breakfast served at the villa, a three-hour island tour, a day trip to Mustique island with a beachside barbecue and free access to facilities at the nearby Grenadine Hills property. (Note: Bequia Beach will be closed June 5 through Oct. 13, 2023). 

Provide Lots of Space 

The more family members who plan to attend a reunion, the more space they’ll need to spread out, relax and have fun. Numerous hotels in the Caribbean are well-designed for multigenerational groups on vacation together. 

At Half Moon in Montego Bay, Jamaica, the Rose Hall Villas have between five and seven bedrooms, as well as private pools and living and dining rooms. The accommodations include the services of a butler, housekeeper and chef. Ocean Club Resorts, which includes two resorts on Providenciales in Turks & Caicos, has accommodations that range from studios to three-bedroom suites. And Frangipani Beach Resort in Anguilla has a four-bedroom villa — and guests can buy out the entire 23-room property for weeklong stays. 

Speaking of buyouts, several other properties offer the option to take over an entire hotel for a truly personalized and private reunion experience. The 14-suite Ani, located near Puerto Plata in the Dominican Republic, offers buyouts for up to 28 guests, while Lovango Resort & Beach Club in St. John, U.S. Virgin Islands, offers buyouts for parties of up to 35 people, for minimum three-night stays, with accommodation options that include new glamping tents, luxury treehouses and a three-bedroom villa. 

Find Activities for All

Family reunions, by nature, involve multiple age groups and interests, so the host hotel must satisfy often-divergent interests. An ideal venue provides diverse activities — as well as plenty that families can enjoy together, regardless of age. 

Bahia Principe Fantasia Punta Cana, for example, has a waterpark, a kids’ club, and lots of live entertainment designed to please multiple ages. 

Rosewood Baha Mar in the Bahamas is home to a Rosewood Explorers Club that can help keep children ages four to 12 busy, while entire families can join volunteer activities at the on-site wildlife sanctuary, pitching in on beach cleanups and other anti-pollution efforts that help protect the local ecosystem.  

In St. Lucia, Windjammer Landing Villa Beach Resort also offers interesting diversions for the entire family, including kayak races, private in-villa cooking classes, private boat tours and horseback riding on the beach. In addition, the property recently debuted the new VIP Kids Program, which offers experiences such as a bonfire story hour and movie nights on the beach. 

Among the newest activity options for Caribbean-bound families is the Private Beach Party Under the Stars program at Sonesta Maho Beach Resort, Casino & Spa in St. Maarten. The offering is available for a minimum of 20 people and includes two hours of bar service and a live DJ.