Best Island for Teens
For teens, it's a toss up between our favorites, where teens can participate in activities with their parents and actually enjoy it! The Cayman Islands is a SCUBA diver's paradise with more than 200 dive sites for teens now old enough to SCUBA, but the British Virgin Islands is a sailor's paradise and teens can learn the ropes and hop the numerous small islands. It just boils down to what you and your teens would most like to try. Resorts on these islands know most visitors are there to get out or in the water and are less likely to cater to those requiring all-day, on-resort activities.
Recommended Resort: Bitter End Yacht Club
Best Island for Infants
Infants are typically easy to please when it comes to an island vacation: plenty of sand and water in which to play. But for mom and dad, perhaps the best place for infants is Jamaica. More specifically the Franklin D. Resort and Spa. This resort assigns every family with their own full-time nanny (included in the cost of the stay). This nanny can put baby down for a nap while mom and dad lounge by the pool, babysit while mom and dad enjoy a quiet dinner, and play with baby when mom and dad enjoy some of the island's adult amenities.
Recommended Resort: Franklin D. Resort and Spa
Best Island for Adventure
The large island of the Dominican Republic is fast becoming the "it" destination for families but has long been considered the adventure capital of the Carribean. The island's rain forests beckon to be explored by foot, zip line and canopy tours' and the long coastline is perfect for surfing, snorkeling, diving, sailing and more. The mountainous interior is also a great place for canyoning, caving and rock climbing, as well as river rafting and mountain biking.
Recommended Resort: Dreams La Romana Resort & Spa
Best Island for Mom and Dad
With more and more all-inclusive resorts offering all-day kids' supervised kids' programs, mom and dad have more time to hit the links, relax in the spa, or explore on their own. We love Aruba for moms and dads because not only is there a wide array of hotel options with programs for kids, but the capital town of Oranjestad is a fantastic shopping city with a number of restaurants, bars and casinos to enjoy. Golf on the coastal north shore provides fantastic views, and spas are aplenty.
Recommended Resort: Radisson Aruba Resort, Casino & Spa
Best Islands for the Budget
Some islands are trickier than others to get to, so even if you find a great deal on a resort, it's important to check out the airfare and connections it will take to get to your final destination. Direct flights are more common to islands like Jamaica, the Bahamas, and Puerto Rico, which is an American Airlines hub. These popular islands are also littered with all-inclusive resorts and family-friendly hotels, making them very competitive and wallet-friendly.
Recommended Resort: Comfort Suites Paradise Island
Best Island for History
All of the islands in the Caribbean are rich in history, many of them once thriving plantation and mill islands or overrun by pirates. We love Puerto Rico for its historic Old San Juan district, where a stroll through the winding streets can easily conjure up feelings of colonial life in the 1500s. Here, Castillo San Cristobal is one of the largest Spanish forts of the new world, and the Castillo San Felipe del Morro citadel provides expansive play areas and views with its dose of history. You'll also find the ancestral home of the Ponce de Leon family and his burial site, at the San Juan Cathedral, in Old San Juan.
Recommended Resort: San Juan Marriott Resort & Stallaris Casino
Best Exotic Island
St. Lucia is considered one of the most beautiful islands in the Caribbean, and with its heavily rain-forested and mountainous landscape around its Pitons and volcano, many feel this island most resembles an exotic Polynesian island. We recommend it because the resorts are spread out and nestled into the mountains and garden landscapes; this is an island that never feels overrun with tourists.
Recommended Resort: Coconut Bay Beach Resort & Spa
Want more ideas? Download our Caribbean Vacation Guide for Families, available only to those who subscribe to our weekly e-letters.
For more family vacation ideas, check out 10 Best Caribbean Family Resorts.