A Great Value Caribbean Escape

Go in December

Many hotels don’t lock in their high-season prices until mid- and sometimes late-December. If nosebleed prices have kept you from a place where you’ve been longing to lounge, see what the room rates are between now and Christmas. For instance, if you’ve been thinking about a long weekend at Hermitage Bay in Antigua, suites that now run between $1,020 and $1,480 a night will cost nearly an additional $500 come February. The same is true at GoldenEye in Jamaica: A Beach Hut that goes for $315 a night until mid-December will be $715 in January.

Home In on a Rental

The variety of sites on offer is tremendous on islands with nonstop flights from the U.S.: beachfront or view-rich hillside; with pool or Wi-Fi or washing machine. Fabulously expensive choices abound, of course, but so do affordable homes, even more so if you’re travelling as a family or group.

Barbados: Most people settle on the west coast, with its excellent restaurants, beautiful beaches and generally placid water. Yet if you, your partner and two kids want to surf, you might like colourful two-bedroom Turtle Cottage high on a cliff in the southeast (from about $200 a night, vrbo.com); or for an unusual stay, check out the Barn Villa on the grounds of what was originally Oughterson Plantation ($120 a night, airbnb.com) and the Cottage Villa ($85 a night, airbnb.com).

Saint Martin: Villa Au Fil de l’Eau’s four bedrooms and pool, near Cul-de-Sac Bay, would provide a chic and elegant respite for four couples vacationing together in high season for roughly $125 per night per person (airbnb.com).

Saint Lucia: Marigot Bay is halfway between Soufrière and Rodney Bay, the two happening towns on Saint Lucia. The airy, roomy Villa St. Lucia, perched above the beach, has a pool and three king bedrooms. For about $1,300 each, three friendly couples could spend a week there in late January (airbnb.com).

Think Town, Not Country

Basing yourself near a town of just the right size can make it easy to access by foot everything you want, from beach to bar to bikini shop. A couple of examples:

Grand Case, Saint Martin: Once a sleepy village along a lovely mile-long beach on the sunset side of the island, Grand Case is still easy to walk through, from one end to the other, and the beach is great for swimming. And, despite vicious slamming by Hurricane Irma in 2017, plenty of restaurants, lively beach bars and shops have reopened, as have charming hotels. Duty-free Saint-Martin is still part of France, which means the flavours of wines, cheeses and charcuterie mix with those of grilled seafood and barbecue from the lolos on the beach.

Willemstad, Curaçao: Originally settled in the 17th century, Willemstad sits on either side of an inlet crossed by a floating pontoon bridge. Candy-coloured Dutch colonial buildings enliven its historic centre, full of hotels and cafes, museums, shops and markets, even casinos, right near lovely soft-sand beaches. Accommodations include villa and apartment rentals and small inns as well as a hotel, Kura Hulanda, within a restored collection of historic buildings along cobblestone streets (from $289 a night, kurahulanda.com).

Avoid the Obvious

Perhaps your idea of a Caribbean idyll requires not only affordability but quiet and uncrowded beaches. If so, head to islands that barely register on the tourist industry’s radar. Often these will require a ferry ride or quick local plane ride after your flight out of the U.S.

Îles des Saintes: If you want all the above but would like it all the better à la française, you can’t improve on a small group of islands to the south of Guadeloupe, two of which are inhabited, Terre-de-Haut and even quieter Terre-de-Bas. Terre-de-Haut offers several small hotels, the most popular of which is the 11-room LoBleu (from $110 a night, lobleuhotel.com).

Barbuda: Though the island is still hurting from Hurricane Irma, Barbuda’s residents are back and rebuilding. At Barbuda Cottages (from $375 for a one-bedroom cottage, three-night minimum, barbudacottages.com), you will have the entire beach to yourself. Barbuda is held collectively by its people, which has kept development small-scale. Find out about the island’s history—as well as where to eat and what to do—at barbudaful.com.


Bethenny Frankelfounder and CEO of Skinny Girl: Puerto Rico’s Old San Juan has that historical international feeling that makes you want to wear bright colours, sip a rum cocktail and dance. El Batey is the most authentic down and dirty bar you can find there. This is where you order a tequila shot, NOT a rosè. The food at Marmalade, also in Old San Juan, is phenomenal. I love the grand nature of the Vanderbilt Hotel, just across town in Condado. It’s a great place for a swanky classic cocktail.

Edward StrongBroadway producer, co-founder of Dodgers Theatricals: In Barbados, my wife and I are always up for an excursion to Hunte’s Gardens in St. Joseph or a catamaran sail from Gibbes Bay up the west coast with Capt Brian Packer. An afternoon beach-bar crawl along the main street of Speightstown is great, as is a sunset Banks beer in Weston on the back porch of John Moore’s rum shop. For a bite beachside, stop at Orange Street Grocer, One Eleven East Beach Bar or Juma’s, all in Speightstown. Don’t miss lunch at the Animal Flower Cave.

Nicole Dennis-Bennauthor of the novels “Here Comes the Sun” (2016) and “Patsy” (2019): I grew up in Jamaica and love to visit family and friends in Kingston, the hub, and in Trelawny—my wife and I held our wedding at a villa we rented there, at Silver Sands, on the beach in Duncans. The villas are private, the beach is beautiful and the community is open-minded, not homophobic. It’s fun to go into Montego Bay next door to visit Pelican Grill for true Jamaican food. Another favourite spot is Floyd’s Pelican Bar, in Treasure Beach, which is built on stilts on a sand bar about a mile out from the shore.

Credit: Alison Humes for The Wall Street Journal, 12 November 2019.