Every Caribbean island has its unique flavor. Some have colonial towns or other sightseeing; others are famous for coral reefs. Families love their all inclusive resorts, but be sure to get out and explore; all resorts arrange tours, and on some islands, it's practical to rent a car and explore on your own.
Families flock to the Caribbean for all inclusive resorts; your choice of Caribbean island may be determined by whether or not it offers all inclusives.
Anguilla
small island, lesser-known as a destination for families eastern Caribbean, just east of the USVI don't expect mega-resorts beautiful beaches; good snorkeling, scuba British influence (incl. left-hand drive) good rating for friendliness and safety* see Family Fun, at the Anguilla site - glassbottom boats, horseback-riding, and other outings.Antigua
small island, near Anguilla365 beaches; snorkeling; scuba day trips to undeveloped sister island BarbudaBritish influencehistoric districts. Nelson's Dockyard National Park, fully restored, is the only Georgian dockyard in the world Jolly Beach is a prominent family-friendly all inclusive resort more about Antigua and Barbuda
Photo courtesy of Aruba Tourist Authority.The "A" of the "ABC" Dutch Caribbean islands, below the hurricane zone Oranjestad town has historic sections 43 nationalities local lingo Papiamento is fun to try don't expect lush terrain name-brand resorts A+ for friendliness, safety* see Aruba for families - resorts, outings and attractions, flights and airports Bahamas
The Atlantis, Bahamas.just a hop from Florida (and technically not Caribbean islands) 700 islands! British influence; historic forts busy areas, quiet areas avoid during Spring Break many resorts, including the unique Atlantis with "waterscape" that includes a shark lagoons, large kids pool area, lazy river, and amazing waterslides Our Lucaya Resort, Grand Bahama, with Westin and Sheraton resorts, is popular with families and has a pool with slides and waterfalls See Bahamas Travel Guide for attractions, travel info, resorts, and more most eastern Caribbean Island; direct flights from the UK “the most British” of the Caribbean islands much-developed, except for the most rugged coastlines considered a safe, friendly island resorts include ritzy (and family-friendly) Sandy Lane, and two all-inclusive Almond Resorts with nurseries "A" for safety, friendly atmosphere* see Barbados for families Bermuda
known for pink sand beaches 180 small islands; seven are connected location is north, 600 miles off N. Carolina; technically not Caribbean low season is Nov.- April, unlike Caribbean Islands safe, upscale, flowery destination British influence sightseeing includes forts, caves Barrier Reef nearby, for scuba and snorkeling resorts, inns, B&B's, cottages A for safety and friendly atmosphere* see Bermuda Island Guide one of the Dutch Caribbean Islands don't expect lush terrain, or big name-brand resorts known for diving the ocean is the big attraction, and Bonaire's fringe reef is a protected national park (Bonaire Marine Park) Buddy Dive Resort welcomes families Dutch, English, Spanish, and Papiamento (creole language) are spoken; kids will enjoy learning a few words of Papiamento see Bonaire For Families - where to stay, attractions and fun outings. 
Photo courtesy of Cayman Islands Department of Tourism.
Photo of Willemstad, courtesy of Curacao Tourism.in the Dutch Caribbean, near Venezuela, and below the hurricane zone don't expect lush terrain fascinating town, Willemstad, is a World Heritage site 70 nationalities on this Caribbean Island local language Papiamento is fun to try all-inclusive Breezes Curacao has kids programs good snorkeling, diving A+ for safety, friendly atmosphere
