Here’s the second installment of the winter getaways I’m dreaming about. If you missed last week’s on Mexico, you can find it here, and I’m working on more, so stay tuned. I’ve made a big push to find more affordable options (obviously a challenge in the Caribbean!), with a few at the end that are on the splurgy side—which means that I have pushed my friends to give me their closely guarded secrets.
Natura Cabana, Dominican Republic. I came here after a friend who could easily afford the Aman said this place was her favorite for all of its soulfulness. Cabanas are scattered throughout the lush tropical property that is on the beach near Cabarete—the decor is on the hippie side, an organic garden supplies their restaurant, and there’s a fantastic rope swing that everyone loves.
Playa Grande Beach Club, Dominican Republic. Celerie Kemble built a cluster of tasteful, pastel-y bungalows in the local vernacular on a fantastic beach.
Auberge de la Petite Anse, St Barths. It’s hard to find approachable options on St Barths, but these colorful bungalows with kitchenettes just off of Flamands Beach, literally right over the water, are so good I am nervous to share. We stayed here on our honeymoon, cooked a lot of our own meals, and even brought our own sheets (Matt has an issue with 50/50 sheets!).
Firefly Estate, Bequia. People who know this tiny, super low-key Grenadine island love it, and many go back every year.
Bequia Beach Hotel, Bequia
Fond Doux, St Lucia. The island is known for its rainforest, and these cottages are surrounded by it.
Ti Kaye, St Lucia. Adults-only resort of little cottages on one of the island’s best snorkeling bays
Montpelier Plantation & Beach, Nevis. Colorful and breezy rooms and villas set on a historical sugar plantation
Jamaica Inn, Jamaica. A small hotel and cottages on Ocho Rios with a somewhat glamorous history (Marilyn Monroe and Arthur Miller supposedly honeymooned here)
Round Hill, Jamaica. So many people I know love Round Hill for its amazing service and history (the hotel opened on a former pineapple plantation in the 1950s with Noel Coward and Babe Paley as part-owners). I was surprised to see that an entry level here in January is $600, though of course some rooms go for much more.
Rock House, Jamaica. Everyone talks about the incredibly fun bar at this Negril hotel, and cliff-jumping into the water.
Kanopi House, Jamaica. An eco-resort of rainforest treehouses overlooking the Blue Lagoon near Port Antonio
Hotel Mockingbird Hill, Jamaica. Simple but comfortable rooms on a mountaintop hotel near coffee country and Port Antonio.
Delphi, Abaco, Bahamas. This fly-fishing lodge has access to nearby bonefishing flats—but there’s plenty for non-fishers to do, too.
Small Hope Bay Lodge, Andros, Bahamas. Relaxed beachfront pine and coral cabins on an island known for diving. Matt has stayed here several times because it’s a great basecamp for bonefishing. It has an old-school family vibe, great staff, few frills, and a great happy hour with homemade conch fritters.
The Other Side, Eleuthera, Bahamas. Not a fan of the word “glamping,” I prefer “safari tent,” which is what they have on this solar-powered property just a 7-minute boat ride from Harbour Island. The owners are incredibly sweet, with excellent taste.
The Ocean View Club, Harbour Island, Bahamas. The same owners as The Other Side. I hear it’s like staying at a friend’s house—it has personality, feels lived in, and no space is off limits—anyone can use the kitchen or make a cocktail.
The Landing, Harbour Island, Bahamas. A historic house on the port side of the island, designed to feel like a Bahamian home. It’s just a short walk to the island’s famous pink-sand beach.
Bahama House, Harbour Island. No, you’re not right on the famous Pink Sands beach, but you’re just minutes away on foot or golf cart. Run by Eleven Eleven, known for their adventure programming, this is a great for those who get antsy sitting on a chaise. Lots of vintage shell-encrusted decor.
Sailrock, South Caicos. White-sand beaches and great snorkeling on the isolated end of Turks & Caicos.
Oasis Grace Bay, Providenciales. Just a two minute walk from Grace Bay Beach.
Dragon Cay Resort, Middle Caicos. The only resort on this part of Turks & Caicos, with big and airy family-friendly villas.
THE STRETCH/HONEYMOON PRICE
Cobbler’s Cove, Barbados. I stayed at this family-owned iconic property a couple of years ago and am crazy about it—the old-school vibe, the decor (Soane rattan—my favorite!), the food (a vigilant approach to sourcing everything locally), the beautiful calm sea in front, and the pink-striped umbrellas and towels. It’s very expensive but I think it’s very special.
Kamalame Cay, Andros, Bahamas. The owners of this remote and incredibly chic property, David and Michael, have made the most special place. Try to book over a weekend when they are having one of their epic all-day luncheons.
Hermitage Bay, Antigua. Their wooden cabins—some of them with pools—set in the hills over a turquoise bay look amazing.
Inn at English Harbor, Antigua. A classic Caribbean-vibed resort on a private beach, with white wooden buildings in a garden setting.
GoldenEye, Jamaica. So many friends have stayed here and loved it, it’s something of a bucket list place for me. James Bond author Ian Fleming’s former estate in Orcabessa Bay was bought and expanded by Island Records founder Chris Blackwell, who supplies all the produce for his hotels (he also owns Strawberry Hill and The Caves) from his organic farm.
Cap Juluca, Anguilla. This icon of the jet-set era with its domed white villas was thoughtfully renovated a couple of years ago by Belmond, ousting the Arabian Nights-style decor in favor of a soft and natural palette. With excellent service and its own Cipriani restaurant.
Rosewood Little Dix Bay, Virgin Gorda, BVI. Alex spent her honeymoon here, and from what we hear, the best aspects of the former Rockefeller resort and its stone-walled beach-front villas have been preserved in the recent major refurbishment (required after it was flattened by Hurricane Irma).
Como Parrot Cay, Turks & Caicos. A friend goes every year for their yoga and Pilates, incredible spa and “the most beautiful beach in the Caribbean.”
Petit Saint Vincent, Grenadines. It’s a private island, so it doesn’t get more secluded than this. Isolated little stone bungalows with sea views, and a big emphasis on locally sourced food.