Anytime the temperature dips below freezing is a good time to daydream about the Caribbean. If you’ve been there, the cold is an excuse to replay favorite beach moments in your brain (preferably while sipping a tropical drink in your living room). Or, if you’ve never been, perhaps last week’s blizzard might have inspired you to plan a trip. If the 1960s quartet the Mamas and the Papas can start dreaming about California when “All the leaves are brown and the sky is gray,” then New Englanders have the right to dream about the Caribbean when all the leaves are gone, and the sky is a bomb cyclone.
Need some ideas? Don’t fret, I’m here to help with some of my favorites. Before I jump into a very subjective list of Caribbean islands I adore, I need to add a very important disclaimer: I haven’t been to every Caribbean island. If your favorite doesn’t show up on my list then there’s a chance I haven’t been there. There’s also a chance I’ve been and it was not my cup of Long Island Iced Tea. Before you go to any of the islands, make sure you check current COVID-19 protocols. Most islands require visitors to be vaccinated. Some require testing before arrival.
Here’s a few gems that I’ve loved.
1. ANGUILLA — Anguilla, with its beaches, beach bars, and some of the best chicken I’ve ever consumed, charmed the shorts off me. In Caribbean island hierarchy, it’s not as glitzy as nearby St. Bart’s, it’s smaller and less populated than St. Martin, and it’s much less commercial than other British outposts, such as the Cayman Islands and Turks and Caicos. There are no fast food chains on the island. Also, no high rises, no cruise ships, and no casinos. What Anguilla lacks in tourist traps it makes up for in white sand beaches (there are more than 30 of them), and hospitality.
2. PUERTO RICO — The island is the best of all worlds in the Caribbean. There are gorgeous beaches, a vibrant capital city, and a culture that combines the comforts of home (Puerto Rico is a US territory) and the balmy climes of the islands. The old city in San Juan may be as touristy as heck when the cruise ships arrive (avoid days and times when the streets are clogged with cruise passengers), but you can always escape with a trip to El Yunque, Puerto Rico’s rain forest.
3. BEQUIA — Bequia (pronounced BECK-way) is the second-largest island in the string of 32 islands that make up St. Vincent and the Grenadines. With a population just over 5,000, it’s an unpretentious place where flights can’t land at night because the tiny airport has no runway lights. There are no big-chain hotels or over-the-top resorts to be found. There isn’t even a Starbucks. There is one ATM machine on the entire island. In short, Bequia is an actual escape in an age where it feels as if there are few true escapes remaining on the planet.
4 and 5. GUADELOUPE and MARTINIQUE — Guadeloupe and Martinique are two separate islands, but I’m pairing them here because both are overseas departments of France, and both feel more rustic than some of their neighboring French islands. On the 430-square-mile island of Martinique, which is sandwiched between Dominica and St. Lucia, rum production is monitored as closely as champagne production in France. Rum tastings at distilleries are almost as impressive as the beaches. If you go to Guadeloupe, you should be in a bathing suit the majority of the time, slathered in fruit salad-scented sunscreen. You should also be stretched out on a large towel gazing at the enticing pale blue ocean. My favorite beach here was Plage du Souffleur on the island of La Désirade, a short ferry ride from Grande-Terre. I have fond memories of some of the bluest water I had ever had the pleasure of floating in. The sand was the color of Benjamin Moore’s Lancaster Whitewash paint. I marveled at how I practically had the beach to myself.
6. SOUTH CAICOS — South Caicos, which is part of the Turks and Caicos archipelago, is a sleepy island where you can escape the crowds of Providenciales, just like celebrities such as Neil Patrick Harris and Justin Bieber. It’s remote enough (an additional flight from Providenciales is necessary to get here) that it helps to thin the crowds, so you’ll often find yourself alone at beaches. That’s a plus if you’re looking to plan your first pandemic-era Caribbean trip. The 8-square-mile island not only has celebrities, it still has donkeys and horses roaming the roads, plus pristine beaches and beautiful snorkeling.
7. ST. LUCIA — The island may be known as a destination for lovebirds and honeymooners, but there’s plenty of other wildlife to be found. It is a hiker’s delight. The island is dominated by the Pitons, and after spending a day photographing them during my visit, I decided I would hike them. There are two, Gros Piton (2,530 feet) and Petit Piton (2,438 feet). There are no trail markers, so guides are necessary. It was an arduous and wet hike (it rained several times), but the view was worth the effort.
8. BARBADOS — If it’s good enough for Rihanna, it’s good enough for you. Barbados is the wealthiest and most developed country in the Eastern Caribbean. Many of the Brits and moneyed Europeans with indeterminable accents who holiday here are looking to let loose, not pinch their pounds when they drop anchor near one of the well-appointed beach clubs for an afternoon of rum cocktails. I was drawn into the beach club scene. During my visit I spent a leisurely afternoon at the Cliff Beach Club. It was all sun-kissed pink cheeks and Gucci sandals under midcentury sputnik light fixtures. From there I moved on to Mullins Beach Bar and Grill, a humbler space with a not-so-humble crowd. Bottom line: This an island best visited when you’ve just received a raise, or you have a hankering to watch cricket or polo matches with a very well-dressed crowd.
9. ST. BART’S — Like Barbados, a good time in St. Bart’s does not come cheap, but it remains a posh paradise. The island, an overseas collectivity of France with a year-round population of 10,000, is best known as an escape for bold names such as Leonardo DiCaprio, Gwen Stefani, and Beyoncé. Many other Caribbean islands depend on mass tourism from cruise ships, but St. Bart’s limits cruise ships to those with no more than 300 passengers. Here, you can shop for goods from top designers and dine in top-notch French restaurants, but you can also sample its 11 free public beaches.
10. CURACAO — The island, 40 miles off the coast of Venezuela, is part of the ABC islands with Aruba and Bonaire. Seized by the Dutch in 1634, it became a self-governing country within the Kingdom of the Netherlands in 2010. The most industrialized of the former Netherland Antilles, Curaçao does not rely on tourism as its sole industry. It is a curious place where one moment you’re soaking in gorgeous ocean views, and the next you’re smelling oil from a nearby refinery servicing the Venezuelan oil fields. Despite the draw back of smelling oil refineries, its signature iguana soup, aloe vera plantations, and ostrich farms give it a distinctly different feel from its Caribbean neighbors.