7 Best Caribbean Vacations: Top Destination Spots And How To Get There

Experience Vibrant Culture And Cuisine On A Puerto Rico Vacation

You’ll never call the Caribbean boring after a vacation to Puerto Rico. Across the island and particularly in the capital city of San Juan, you’ll marvel at the colorful public art, Spanish colonial ruins and mouthwatering street food. You may even come home with some salsa dancing skills.

In free-spirited Santurce, a San Juan neighborhood many regard as the best Caribbean vacation spot for art, visit its many galleries and museums or simply walk around and admire the graffiti art, mosaics and murals that grace the sides of buildings. Spot larger-than-life bronze sculptures or wander into an open-air festival for an immersion into Puerto Rico’s creative energy. In the southern city of Ponce, The Museo de Arte de Ponce houses more than 4,500 pieces of art, making it the largest art museum in the Caribbean. 

Explore centuries-old forts like El Morro and Castillo San Cristóbal in Old San Juan, a historic district within the city, and snap photos of its candy-colored buildings. Take a break to sample Puerto Rican specialties like mofongo, lechón asado, or pasteles from a food truck or beachside restaurant.  

Swim With Turtles And Stingrays On The Beach In Family-friendly Grand Cayman

For a family vacation that’s not overwhelming, Grand Cayman has all the thrills of a theme park without the chaos. You’ll find calm, shallow waters; guided animal encounters; and family-friendly restaurants across this Caribbean vacation destination.  

At Stingray City, there’s no minimum age to interact with the friendly cartilaginous fish. Kids can wade in the shallow waters of the sandbar, feed the gentle animals and even go snorkeling in the crystal-clear waters. Combine it with a visit to Starfish Point to further your marine life exploration. Learn about sea turtle conservation at Cayman Turtle Centre and swim alongside them at the Turtle Lagoon.

The best waters for kids can be found at Seven Mile Beach, which also offers shipwreck sites to explore. When it’s time to eat, it won’t be hard to find chicken fingers and fries — menus across the island skew family-friendly.

Indulge In Colonial History And Comfort Food On A Dominican Republic Vacation

The best Caribbean vacation for history buffs might be Dominican Republic, an island that dates back to the 15th century when Columbus landed there in 1492. The capital city, Santo Domingo, is the oldest continuously inhabited European settlement in the Americas, and the city’s Colonial Zone is a UNESCO World Heritage Site. Near Taino Bay in Puerto Plata, learn how the island defended itself from pirates at Fortaleza San Felipe, a 16th-century fortress. Gaze on prehistoric gems at the Amber Museum, where amber specimens date back 25-40 million years. 

After exploring, indulge in Dominican comfort food like sancocho (a hearty meat and vegetable stew) or pescado con coco (fish cooked in coconut milk). Dominican cuisine is a flavorful melding of influences including Taino, Spanish and African. 

What To Consider When Booking A Caribbean Vacation

How do you choose the best Caribbean vacation for you? Whenever I take a cruise, I find myself relaxing into the experience; it’s freeing not to have to worry about logistics like checking into hotels, navigating airports or planning meals. I trust that the shore excursions offered by reputable cruise lines like Royal Caribbean have been vetted by experts and will be a value-add to my trip. Plus, if you’re worried about missing one destination for another, a cruise is often a budget-friendly way to make the most of limited vacation days and experience multiple destinations in one vacation, all without repacking your bags.