I've Stayed at More Than 50 Hotels in the Caribbean—These 12 Keep Me Coming Back Again and Again

Travel + Leisure

4 days ago

The Caribbean, with its oversized, over-the-top resorts set along white-sand, sugary beaches, has long been a go-to destination for winter-weary travelers looking to fly and flop. And there are literally hundreds of options that travelers could choose from.
As a full-time writer who covers culture, cuisine, and travel, I've stayed at some of the best properties in the region, from an all-inclusive private island in the Dominican Republic to a home away from home in the heart of historic Havana.
In fact, I've stayed at more than 50 hotels in the region—and in my opinion, these 12 are the best hotels in the Caribbean. Private plunge pool at Sandal's Saint Vincent and the Grenadines.
Freshly debuted last spring, Sandals St. Vincent & the Grenadines is the perfect marriage between ultra-luxury and adventure, and it's the first all-inclusive resort of its kind in the archipelago nation that should be on every traveler's radar. This luxe 301-room property has 11 food and dining venues, four pools, and a sumptuous spa. At Buccan, chefs employ traditional solid fuel-driven cooking techniques to prepare island-grown meals.
Splurge and stay in one of the property's premium Vincy Overwater Two-Story Villas. These overwater bungalows come complete with butler service, outdoor soaking tubs with rainfall showers, and rooftop lounges for an experience that will make you wonder why anyone would ever fly all the way to the Maldives. Location: St. Vincent and the Grenadines
St. Vincent and the Grenadines Nearest Airport: 15 miles to Argyle International Airport (SVD)
15 miles to Argyle International Airport (SVD) Family-friendly or Adults-only: Adults-only
Adults-only Restaurant Reservations: Reservations are required at some restaurants.
Reservations are required at some restaurants. Accessibility: Two rooms are accessible, and a beach wheelchair is available to borrow.
Two rooms are accessible, and a beach wheelchair is available to borrow. Rates: $$$ Wooden deck overlooking the ocean at Secret Bay.
I get asked for honeymoon recommendations on a shockingly frequent basis for a single person. Secret Bay is my top pick every time, an all-villa property on the untouched island of Dominica that has been named by T+L readers as the best resort in the Caribbean for three years running.
Secret Bay's collection of twenty-three villas has private plunge pools and butler service, and expansive indoor-outdoor living space with views ranging from rainforest to the Caribbean Sea. Simply waking up in paradise is its primary appeal, though you'll be tempted to emerge from your villa yoga classes in the new wellness pavilion, stand-up paddleboarding by the beach, or cooking classes and chef-driven menus at the oceanview restaurant. Location: Portsmouth, Dominica
Portsmouth, Dominica Nearest Airport: 23 miles to Douglas-Charles Airport (DOM)
23 miles to Douglas-Charles Airport (DOM) Family-friendly or Adults-only: Family-friendly
Family-friendly Restaurant Reservations: Reservations are not required.
Reservations are not required. Accessibility: Select villas are fully wheelchair accessible, as are facilities like the bar, pool area, and beach. Staff have received training on the needs of travelers with disabilities.
Select villas are fully wheelchair accessible, as are facilities like the bar, pool area, and beach. Staff have received training on the needs of travelers with disabilities. Rates: $$$ Left: Guest room; Right: Walkway at Cottage Club Hotel.
Perched on a hillside on one of the smallest islands in the Caribbean, The Cottage Club is a destination so special that I almost feel tempted to keep it to myself. With its stately Great House and a collection of just 10 private cottages built to blend into the white-wall, red-roof Saban architectural aesthetic, The Cottage Club is one of just a few hotels on an island of around no more than 2,000 people. It's hard to say whether it was the unrivaled hospitality or incredible adventurous activities, like world-class diving or summiting the island's volcanic peak, Mount Scenery, that made my visit so memorable. Regardless, untouched-by-time Saba is unexpectedly one of the coolest places to be in the Caribbean. Location: Windwardside, Saba
Windwardside, Saba Nearest Airport: 3 miles from Juancho E Yrausquin Airport (SAB)
3 miles from Juancho E Yrausquin Airport (SAB) Family-friendly or Adults-only: Family-friendly
Family-friendly Restaurant Reservations: N/A
N/A Accessibility: Rooms and facilities are not wheelchair accessible and no real accommodations for guests with mobility issues are provided.
Rooms and facilities are not wheelchair accessible and no real accommodations for guests with mobility issues are provided. Rates: $ Nova Lounge at Oil Nut Bay.
The North Sound of Virgin Gorda might be the most sought-after zip code in the Caribbean, and at its heart is Oil Nut Bay, which feels like a private island. Cut off from the rest of Virgin Gorda and accessible only by boat and helicopter, its supreme seclusion is a part of its unending appeal. This oversized 400-acre property stretches between both the Caribbean and Atlantic coasts of the island, home to oceanview suites and spacious villas, and estates available for rent when owners are traveling elsewhere. It's pure laidback luxury at the property's private beach club, sports courts, kids' club, and gym, with an overwater bar and restaurant welcoming visitors to spend the entire day in this corner of paradise. The property's brand new overwater spa will debut soon, a perfect excuse for a return visit, if you ask me. Location: Virgin Gorda, British Virgin Islands
Virgin Gorda, British Virgin Islands Nearest Airport: 12 miles from Virgin Gorda Airport (VIJ) or 20 miles from Terrance B. Lettsome Airport, Tortola (EIS)
12 miles from Virgin Gorda Airport (VIJ) or 20 miles from Terrance B. Lettsome Airport, Tortola (EIS) Family-friendly or Adults-only: Family-friendly
Family-friendly Restaurant Reservations: Reservations are not required.
Reservations are not required. Accessibility: A selection of single-level villas is available for guests using wheelchairs, and all of the property's restaurants are wheelchair accessible.
A selection of single-level villas is available for guests using wheelchairs, and all of the property's restaurants are wheelchair accessible. Rates: $$. Guest bedroom at Playa Grande Beach Club.
Hidden away on a still untouched stretch of coastline on the north coast of the Dominican Republic, Playa Grande Beach Club is the utter antithesis of the oversized resorts and busy beaches of Punta Cana. Eating freshly fried plantain chips and sipping coconut mojitos from your private patio or beneath a fringed umbrella on the white sand beach is the name of the game here. With just a handful of private bungalows, ranging from one to three bedrooms, you'll have this corner of the coastline almost all to yourself to enjoy. However, should the inspiration strike to get out and explore, whale-watching in the cooler months and hikes to crystal clear lakes and lagoons in the summer are themselves worth traveling for. Location: Rio San Juan, Dominican Republic
Rio San Juan, Dominican Republic Nearest Airport: 49 miles to Gregorio Luperón International Airport (POP)
49 miles to Gregorio Luperón International Airport (POP) Family-friendly or Adults-only: Family-friendly
Family-friendly Restaurant Reservations: Reservations are not required.
Reservations are not required. Accessibility: Facilities and rooms are not wheelchair accessible and require navigating steps to access.
Facilities and rooms are not wheelchair accessible and require navigating steps to access. Rates: $$$ Exterior of Half Moon at night.
Take a peek inside the stately Founder's Cove at Jamaica's Half Moon Resort and you'll see photos of superstars, past presidents, and even the Royal Family adorning the walls. What started as a small collection of cottages along a then-untouched Montego Bay beachfront has blossomed into a legacy of luxury that continues today. A championship golf course, numerous sports courts, a new fitness center, and a Salamander Spa with an impressive menu of treatments and wellness experiences keep guests coming back again and again. Locals and visitors alike come from far and wide to dine here, too; the property's historic Sugar Mill Restaurant is one of the most celebrated restaurants in the Caribbean, though the newer Delmare is arguably even better with an Italian-meets-Caribbean menu with standout dishes like Blue Mountain coffee-infused pasta that blew me away. Location: Montego Bay, Jamaica
Montego Bay, Jamaica Nearest Airport: 5.5 miles to Sangster International Airport (MBJ)
5.5 miles to Sangster International Airport (MBJ) Family-friendly or Adults-only: Family-friendly
Family-friendly Restaurant Reservations: Reservations are required at some restaurants.
Reservations are required at some restaurants. Accessibility: Seven guest rooms are fully ADA-compliant, and all resort facilities are wheelchair accessible. A beach wheelchair is available to borrow.
Seven guest rooms are fully ADA-compliant, and all resort facilities are wheelchair accessible. A beach wheelchair is available to borrow. Rates: $$ Aerial view of the pool at Alaia Belize.
Taylor McIntyre/Travel + Leisure
Alaia Belize draws the vacation-ready with its modern, modular design style and luxurious amenities that only add to the island's boundless appeal. Even standard rooms come with private outdoor space to enjoy tropical breezes, but suites offer terraces so spacious they could be an entire room in their own right. Accommodations aside, the resort's pièce de résistance is the adults-only rooftop swimming pool and eatery serving sushi, ceviche, and the freshest shrimp tacos I've ever had outside of Mexico. Grab one of the property's golf carts for an excursion up to the white sand Secret Beach or for a jaunt into San Pedro for some shopping or local bites at Elvi's Kitchen and drinks at the overwater restaurant Palapa. The property's dedicated dive shop makes exploring the reef even easier, offering everything from beginner-friendly PADI certifications to advanced diving classes in preparation for taking on Belize's world-famous Great Blue Hole. Location: San Pedro, Ambergris Caye, Belize
San Pedro, Ambergris Caye, Belize Nearest Airport: 1.5 miles from John Greif II Airport (SPR)
1.5 miles from John Greif II Airport (SPR) Family-friendly or Adults-only: Family-friendly
Family-friendly Restaurant Reservations: Reservations are not required.
Reservations are not required. Accessibility: Elevators and ramps make parts of the property accessible, though rooms and pool areas lack adaptations for wheelchair users.
Elevators and ramps make parts of the property accessible, though rooms and pool areas lack adaptations for wheelchair users. Rates: $$ Aerial view of the beach at Baoase Luxury Resort.
Baoase Luxury Resort is a serene and secluded property named after an oasis. It's lush and green, and set on a private white cove beach where Balinese-inspired villas and cottages pop up from the sand. This tranquil 23-key spot feels intimately designed for a romantic getaway where you'll be tempted to go no further than your own room, especially if you spring for one with a private pool. When you do, the whole of this infinitely appealing island awaits, still a mostly hidden haven with spectacular snorkeling and beaches that feel blissfully bare compared to those on neighboring islands. The restaurant here is one of the best in the Caribbean, part of a sizzling culinary scene that has contributed to the island's blossoming in a way I could have never imagined when I first visited more than 15 years ago. Location: Curaçao
Curaçao Nearest Airport: 9 miles to Hato Curaçao International Airport (CUR)
9 miles to Hato Curaçao International Airport (CUR) Family-friendly or Adults-only: Family-friendly
Family-friendly Restaurant Reservations: Reservations are required.
Reservations are required. Accessibility: This property is not wheelchair accessible and does not offer any accessibility features for guests with vision or hearing impairments.
This property is not wheelchair accessible and does not offer any accessibility features for guests with vision or hearing impairments. Rates: $$$ Guest room at Caerula Mar Club.
I had heard that Caerula Mar Club on South Andros Island in the Bahamas was the only resort of its kind on the island, but I didn't realize just how unique it was until I grabbed a paddleboard and took it in from the water. All along the island's palm-fringed coastline, there are barely any other structures in sight, other than this 2021 It List hotel.
During my stay at this 23-key boutique property, I met all sorts of guests. Some were here to fish for tarpon and bonefish, while others simply wanted to unplug and unwind for a week. All of them, however, felt lucky to have snagged one of the few precious rooms at this tropical escape. And don't be surprised if you meet a lot of Canadian guests here; Caerula Mar is much more famous than its small size might let on. It was featured in HGTV Canada's Island of Bryan , which followed owners Bryan and Sarah Baeumler throughout the years-long renovation process. Caerula Mar Club's appeal now far surpasses its 15 minutes of fame, and welcomes visitors who come back year after year.
Location: South Andros Island, Bahamas
South Andros Island, Bahamas Nearest Airport: 3 miles to South Andros-Congo Town-Queen Airport (COX)
3 miles to South Andros-Congo Town-Queen Airport (COX) Family-friendly or Adults-only: Family-friendly
Family-friendly Restaurant Reservations: Reservations are not required.
Reservations are not required. Accessibility: Some rooms and facilities are wheelchair accessible, though flight transportation to and from the island is not wheelchair friendly, making access challenging.
Some rooms and facilities are wheelchair accessible, though flight transportation to and from the island is not wheelchair friendly, making access challenging. Rates: $$ Guest room in La Reserva Vedado.
Years of traveling to visit family in Havana have taught me that the best places to stay are found outside the city's tangle of colonial-era streets and in stately, century-old mansions like La Reserva Vedado. This heritage home sits along a quiet side street shaded by banyan trees in one of Havana's poshest neighborhoods, with white columns and an ample patio with rocking chairs greeting guests. To stay here feels like coming home, each of its 11 rooms and suites are uniquely designed but have luxe details like soaring ceilings and original tile floors. The property's lush garden has an intimate cafe and restaurant with indoor-outdoor seating. Sign up for the guest-favorite mojito-making class with the bartender before heading to the nearby Malecón Sea Wall to take in the sun setting over the ocean. Location: Havana, Cuba
Havana, Cuba Nearest Airport: 12 miles from José Martí International Airport (HAV)
12 miles from José Martí International Airport (HAV) Family-friendly or Adults-only: Family-friendly
Family-friendly Restaurant Reservations: Reservations are not required.
Reservations are not required. Accessibility: Certain rooms are wheelchair accessible and showers have grab bars, though restaurant and garden spaces would be more challenging to navigate.
Certain rooms are wheelchair accessible and showers have grab bars, though restaurant and garden spaces would be more challenging to navigate. Rates: $ Bedroom in Sara's Cabin at Finca Victoria.
It's nearly impossible to pull me away from the culture and cuisine of sizzling San Juan, Puerto Rico, but if there's one place that can do it, it's Finca Victoria in nearby Vieques. A T+L It List property, Finca Victoria feels like any other place in the Caribbean. The property's commitment to wellness goes far beyond the basics: it's the only Ayurvedic hotel in the Caribbean and a popular Panchakarma retreat center complete with complimentary daily yoga classes and a spa menu with everything from traditional massages to Chinese medicine-inspired treatments. Wellness retreat or not, I will never get over the treehouse suites here, which are stunningly beautiful. Larger estate-style rooms and a brand-new Airstream will have you booking your return visit before your first stay comes to an end. Location: Vieques
Vieques Nearest Airport: 2 miles to Antonio Rivera Rodríguez Airport (VQS)
2 miles to Antonio Rivera Rodríguez Airport (VQS) Family-friendly or Adults-only: Adults-only
Adults-only Restaurant Reservations: Reservations are not required.
Reservations are not required. Accessibility: The property offers one wheelchair-accessible room, plus a removable ramp that can be added to access many facilities, though paths and unpaved areas may be challenging to navigate.
The property offers one wheelchair-accessible room, plus a removable ramp that can be added to access many facilities, though paths and unpaved areas may be challenging to navigate. Rates: $$ A bedroom in a Cayo Levantado Resort villa.
Set on the white sands of a palm-fringed private island in the Dominican Republic, Cayo Levantado Resort is tailor-made for beachside indulgence. This It List hotel has pools scattered across the property as well as oceanfront bars and eateries, making it as easy to spend an entire stay just steps from the water. But the real standout amenity of Cayo Levantado Resort is its wellness program, considered among the very best in the Caribbean. I'll be the first to admit that I arrived a total skeptic, but by the end of a breathwork and sound healing session, I was having an out-of-body experience (seriously). Serenity seekers could easily spend days on end at the Yubarta wellness center in the verdant heart of this tropical island, learning aerial yoga, getting energy healings, and sitting in on dream analysis from trained practitioners. Location: Samaná, Dominican Republic
Samaná, Dominican Republic Nearest Airport: 35 miles to Samaná El Catey International Airport (AZS)
35 miles to Samaná El Catey International Airport (AZS) Family-friendly or Adults-only: Family-friendly
Family-friendly Restaurant Reservations: Reservations are required at some restaurants.
Reservations are required at some restaurants. Accessibility: The property is accessible only by boat, a challenge for visitors with mobility concerns, though facilities and rooms offer accessibility measures to make navigating the island easier.
The property is accessible only by boat, a challenge for visitors with mobility concerns, though facilities and rooms offer accessibility measures to make navigating the island easier. Rates: $$
Summertime travel has never been hotter in the Caribbean, with many vacationers only now realizing that this warm-weather escape is pretty dreamy year-round. Once the throngs of travelers return home in mid-April, resorts slash rates and bare beaches abound. Many locals insist the islands are at their best in the rainier months of the summertime with all their green tropical lushness, and for travelers who don't mind a passing afternoon shower, I tend to agree!
Off-season travel certainly comes with its perks, but it also coincides with Atlantic hurricane season, which stretches from June to November. Visitors should purchase travel insurance and check with their hotel or resort about weather-related cancellation policies prior to departure. Islands outside the hurricane belt, such as Aruba, Bonaire, and Curaçao, or Caribbean-facing coastal spots in the Americas like Cartagena, Colombia, or Bocas del Toro, Panama, can also make convenient alternative destinations during the summertime.
Planning a Caribbean vacation spanning multiple islands can be more complex and costly than many travelers realize. While certain islands are well connected by ferries or water taxis, like the British Virgin Islands, in many areas, ferries are infrequent, costly, or non-existent. Even flights between islands are less frequent and more expensive than most travelers realize, often requiring passengers to transit through hubs like San Juan, Miami, or Fort Lauderdale. Can't shake the desire to cross multiple islands off your bucket list in one trip? The ferry system connecting St. Lucia, Dominica, Guadeloupe, and Martinique is one of the region's best.