White sands and glistening seas characterize each of the idyllic islands of the Caribbean. But as frequent travelers know, the similarities between the islands essentially stop there. Every destination harbors a unique culture and appeal that you won’t find on a neighboring shore, and some waters are more suited for watersports than others.

From surfing in San Juan to deep-sea fishing in Nevis, here are our favorite destinations for chasing passions on the water. Tradewind can get you there with hubs in San Juan, Puerto Rico, Antigua, and St. Thomas.

Surfing | Puerto Rico

Photo credit:  WOW Surfing School

Photo credit: WOW Surfing School

There’s a reason Puerto Rico is so often listed as a top Caribbean surf destination, and it has everything to do with the consistent, year-round waves. Fall and winter may be the best times to visit the island for swell, but surfers will find quality waves during all seasons, even summer, with the best places to paddle out being the north and northwest coasts. If you prefer to stay close to San Juan, head to Playa Aviones—a crowded but reliable surf spot revered by locals and visitors alike. Or for a more far-flung adventure, cruise along the coast to Rincon or Aguadilla to find some of the island’s best breaks.

Our Recommendation: Rent a board at WOW Surfing School in San Juan on your way the beach, or stay for a lesson for beginner and intermediate surfers.

Sailing | Antigua

Photo credit:  Horizon Yacht Charters

Boating has always been at the heart of Antigua’s culture, from weekly races on the water to annual regattas that draw seafarers from all over the world. (Devoted sailors should plan to attend Sailing Week in the spring.) And with an estimated 365 beaches and countless places to drop anchor, it’s easy to see why. You could spend an entire year circling the little island and wake up to a different stretch of shoreline each day. Antigua is also known as one of the top sunset spots in the Caribbean, making it a beautiful place for experienced boaters and those simply wishing for an evening sail on the Caribbean.

Our Recommendation: Horizon Yacht Charters in Jolly Harbour Marina offers sailing charters and week-long classes designed to give you the skills needed to handle a 33 to 40-foot watercraft.

Kitesurfing | St. Barth


When it comes to kitesurfing in the Caribbean, you’d be hard pressed to find a more beautiful spot than the serene waters of St. Barth. Consistent winds and glassy seas have made it a preferred destination for professional kitesurfers and windsurfers alike, with Grand Cul de Sac considered to be the best location on the island. The tradewinds blowing in from the Atlantic mean the shallow bay is often experiencing 15-20 mile-per-hour conditions—perfect for kitesurfing—while a protective coral reef keeps the waters calm for beginning and experienced athletes to enjoy.

Our Recommendation: Reach new heights with a kitesurfing lesson from Saint Barth Kite. Most sessions take place in Grand Cul de Sac, but experienced kitesurfers can head into the deeper seas of Saline with a southeastern wind.

Diving | Anguilla

Photo credit:  Shoal Bay Scuba Shack

Photo credit: Shoal Bay Scuba Shack

The tranquil seas around Anguilla are a snorkeler’s paradise, teeming with vibrant schools of fish and magnificent sea turtles, but some of the most spectacular sights and experiences are found at greater depths accessible only to scuba divers. The island is home to seven marine parks filled with beautiful rock formations, shipwrecks, and an array of sea life that doesn’t venture so close to the surface. First-time divers in the area should make time for Stoney Bay Marine Park, Anguilla’s first underwater heritage sight. Here you can explore an 18th century sunken ship that still has its cannons, anchors, and other fascinating finds.

Our Recommendation: Shoal Bay Scuba Shack, located in The Valley, assists beginning divers with Open Water certification and more experienced divers with obtaining a Master certification.

Kayaking and Paddleboarding | St. Thomas

Photo credit: Jimi Smith

Photo credit: Jimi Smith

You will likely have a wonderful kayaking or paddleboarding experience anywhere in the Caribbean, but there are some places like St. Thomas that are simply unparalleled. Beginners will enjoy exploring the calm Caribbean bays, while more experienced paddlers may wish to travel to protected wildlife preserves like Bird Island and Cas Cay. In any case, you’re sure to see an abundance of vibrant marine life, especially if you opt for a clear bottom kayak. And for those looking for even more, sign up for a night paddling tour in a kayak or on a paddleboard equipped with LED lights. You’ll be able to observe sea creatures that only come out at night—an experience truly unlike any other.

Our Recommendation: Grab your rental or sign up for an island tour with the Adventure Center, located on-site at Marriott Frenchman’s Reef Resort.

Charter Fishing | Nevis


The little island of Nevis may not seem like the obvious destination for charter fishing, but it’s in these waters that visitors truly experience the abundance of the sea. Cast your line close to shore in hopes of hooking snapper and grouper among the reefs, or opt for a deep sea fishing excursion where you may come across wahoo, mahi-mahi, mackerel, tuna, and marlin. There are many sport fishing boats departing from Nevis—as well as some larger yachts departing from the nearby St. Kitts—that can accommodate you for half or full day charters. Most captains are also willing to customize trips to include snorkeling, visits to nearby islands, and watching the sunset over the Caribbean Sea.

Our Recommendation: Whether you’re an experienced angler or family with young children, Caribbean Catch in Cades Bay will tailor a cruise right for you.