Escape the cold this winter with these Caribbean island getaways

  • 4 min to read
Escape the cold this winter with these Caribbean island getaways

Like it or not, winter is coming. For chilly New Englanders, few things beat a body- and soul-warming trip to the Caribbean. But choosing the perfect island destination can send shivers down anyone’s spine. Whenever I search for a rejuvenating island getaway, a set of travel-tested criteria guides my decision. I want a place with unspoiled beaches, some semblance of a local culture, profound beauty, and plenty of options for swimming, snorkeling and sailing. Perhaps most importantly, the island should still be under the radar enough so it’s not overrun with tourists, or at least part of the island remains off the beaten path. Here are four locales that fit the bill and will chase away those cold-weather blues.


Admiralty Bay off Port Elizabeth on the southwest end of Bequia sits in the shadow of 760-foot-high Mount Pleasant and is a popular destination for the yachting set. In Port Elizabeth, dive shops, canvas repair facilities, the Bequia Marina, a large ferry terminal and restaurants cater to both visitors and residents.


St. Vincent and the Grenadines

Pronounced bekway, this 7-square-mile island in the southeastern Caribbean is home to about 6,000 people who remain true to their maritime roots as sailors, fishermen and boat builders. One of 32 islands making up the former British colonies of St. Vincent and the Grenadines, it’s accessible via a small plane from Barbados — before the airport was built in 1992 it was only reachable by boat — and has been saved from overdevelopment. One of the quieter corners of the Caribbean, Bequia has no imposing resorts obstructing the view. Instead, there are simple guesthouses, villas and hotels that blend in with the environment. Port Elizabeth is the only town, with colorful, ramshackle buildings amid palm trees. Transportation on the island is by land or water taxi, car rental or inexpensive Dollar Van, the island’s answer to public buses and a great way to sample the local culture. Also get some local flavor by attending a music festival or boat regatta.

Bequia is well suited for fishing, snorkeling, relaxing and swimming. Most tourists head to Princess Margaret Beach, while locals go to the next-door Lower Bay, home to the open-air restaurant and bar De Reef, right on the beach. They serve fresh seafood, piña coladas and fried chicken while local musicians play. There may be an opportunity to get into a game of Mexican dice, and if you don’t know how to play, someone will teach you. Friendship Bay is on the windward side, and while it is sheltered, it’s slightly more built up. Industry Bay has remains of a sugar plantation, with a more rugged coastline similar to its neighboring Spring Bay; while these two bays offer no services, they make up for it in privacy.


Culebra’s Flamenco Beach is unspoiled aside from the rusted tanks left behind by the U.S. military, which used the tropical location as a testing ground for its equipment before entering World War II.


Island off Puerto Rico

A nonstop flight to San Juan, and then a puddle jumper or a 45-minute ferry ride from Fajardo, will get you to the Puerto Rican paradise of Culebra. Once there, bicycle, scooter, jeep or the público is the mode of transport.

Sitting off Puerto Rico’s east coast and with only a couple thousand residents in its 11 square miles, Culebra is for nature lovers. There are no oversize resorts or hotel chains — only comfortable inns, guesthouses and vacation rentals. Here you can swim among sea turtles and rays at Tamarindo Beach, catch waves at Zoni Beach or snorkel the unspoiled coral reefs at the beach of Carlos Rosario, a 25-minute walk down a dirt path from Flamenco Beach.

Hailed by the Discovery Channel as the second-most beautiful beach in the world, Flamenco will not disappoint. It’s surrounded by lush vegetation and rolling hills that frame the gorgeous turquoise water. It’s color like you’ve never seen. Be sure to have lunch at one of the food trucks permanently parked there, which serve empanadillas (turnovers stuffed with seafood or meat), sorrullos (“Puerto Rican fries” with corn flour and cheese), pinchos (pork, chicken or fish skewers) and fried plantains.

St. Martin_Grand Case 2.jpg

Grand Case Beach just might be the best of the dozens of beaches on St. Martin.

St. Martin

French West Indies

While St. Maarten and St. Martin share an island in the Lesser Antilles along the eastern edge of the Caribbean Sea, they are completely different. Occupying the southern part of the island, St. Maarten belongs to the Dutch. It’s extremely built up with high-rise, beachfront condominiums and jam-packed with stores, nightclubs and casinos. Except for the beaches, you’d hardly know you were in the Caribbean. By contrast, the northern St. Martin, owned by France and part of the French West Indies, still retains some of its original charm. The capital village of Marigot has gingerbread houses, sidewalk cafes and a vibrant craft and produce market on Wednesdays and Saturdays.

Category 5 Hurricane Irma did a number on St. Martin two years ago. While there is still work to be done to repair the damage, plenty of progress has been made and the island is welcoming visitors once again.

St. Martin has 37 beaches in total. (Most are clothing optional or at least topless.) Every beach I’ve visited (Friar’s Bay, Cupecoy, Mullet Bay, Happy Bay, Long Bay and Petites Cayes) has been equally beautiful, but Grand Case Beach is, by far, my favorite. The mile-long curl of white sand and calm waters is a great place for swimming and snorkeling. And it’s here you find the real St. Martin. It’s a small fishing village with traditional architecture; gourmet restaurants; seaside bars with sand service, sand floors and live music; and lolos, open-air barbecue stands serving huge portions of Caribbean cuisine such as ribs, lobster, chicken, fish, goat stew, rice and peas, cod fritters and johnnycakes. It’s a real slice of life.

St. John_Lameshur Bay.jpg

Lameshur Bay is on St. John’s rugged south shore and is just remote enough to scare away the crowds.

St. John

U.S. Virgin Islands

It’s not easy to get to St. John, the smallest of the three U.S. Virgin Islands and due east of Puerto Rico and Culebra, but it’s worth it. You have to fly into neighboring St. Thomas, grab a cab and drive 45 minutes through crowded streets before being deposited at the ferry dock in Red Hook for a 20-minute crossing. But as soon as you exit the boat in Cruz Bay, all of life’s tensions magically drift away. Two-thirds of St. John is part of the Virgin Islands National Park. The beaches are pristine, public and plentiful, and with over 40 percent of the park underwater, there’s great snorkeling as well.

Cruz Bay is the main town with the most amenities and the most tourists. A more secluded spot is Coral Bay on the opposite end of the island. You can get there by car rental, bus or taxi. It’s petite with a few bars, restaurants and two grocery stores, but it’s more authentic with its community of salty liveaboard sailors, artists, musicians and professional drinkers. Since most tourists don’t venture this far, the bays and beaches are less populated, if at all. A great way to explore is by charter boat. I spent many happy days onboard the Poet’s Lounge, sailing from one swimming and snorkeling spot to another.

This article appeared in the November 2019 issue of Connecticut Magazine. You can subscribe here, or find the current issue on sale hereSign up for our newsletter to get the latest and greatest content from Connecticut Magazine delivered right to your inbox. Got a question or comment? Email, or contact us on Facebook @connecticutmagazine or Twitter @connecticutmag.