Hidden among the Caribbean’s many mega-resorts are some of the most unique, intimate boutiques travelers can imagine. With laid-back, eco-friendly attitudes, these petite hotels are some of the best in the region, offering personalized service and truly relaxing atmospheres. So consider passing on that 500-room all-inclusive and indulge in some intimacy at these wonderful boutiques.
The gorgeous Fowl Cay Resort feels more like a private home than a hotel.
Crowded beaches are unheard of on this private island resort where a maximum of 28 guests at a time have free range of 50 acres and three beaches. Personal boats for daily excursions, on-call service, spacious villas with fully stocked kitchens and wet bars, and a host of all-inclusive activities make Fowl Cay a standout gem in the Exumas. Read More »
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Bahamas,
Barbados,
Beach Hotels,
Boutique Hotels,
British Virgin Islands,
Caribbean,
Dominican Republic,
Federation of St. Kitts and Nevis,
Jamaica,
St. Barts,
St. Lucia,
Turks and Caicos
Rockhouse Hotel
There’s nothing quite like the sense of discovery one feels when arriving at a hidden gem hotel — a truly special spot that is intimate, remote, underrated, or all of the above. Some people like to brag to their friends about their insider find; others prefer to keep it all to themselves. Of course, we at Oyster have never been good at keeping secrets.

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Aruba,
Barbados,
Boutique Hotels,
British Virgin Islands,
Caribbean,
Dominican Republic,
Jamaica,
Puerto Rico,
St. Lucia
by Jane on February 20, 2013
It’s time to get your spring break plans in order, and if you’re looking for some fun in the sun, the Caribbean is a prime destination. But with thousands of islands (although only a few dozen are inhabited) to choose from, that doesn’t narrow things down much. That’s why we at Oyster have created an A to Z (well, actually, an A to V) guide to the Caribbean, so choosing your island and resort will be a piece of cake. First stop: Anguilla.
The boutique Anacaona has two pools.
Anguilla is a tiny British territory that covers fewer than 40 square miles and is a popular spot for couples and celebs (Sofia Vergara went on a girls’ trip to the island) due to its small size and upscale vibe. Visitors must either fly to St. Martin and take a short ferry to the island, or fly in directly (by way of a small seaplane) from San Juan, Puerto Rico. Thus, getting to the island can be pricey. So once you’re there, we’d recommend staying at the boutique Anacaona in the island’s West End. Though its not quite as luxe as the CuisinArt or Viceroy, it offers access to the same gorgeous white-sand beach as the neighboring Viceroy – through an off-property path — as well as to the nearby Greg Norman’s golf course and a few restaurants, and its prices are considerably lower. With two small pools, a great restaurant serving Caribbean fare with a twist, and a massage hut on the beach, the hotel is a good pick for value.
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Anguilla,
Aruba,
Bahamas,
Barbados,
Boutique Hotels,
British Virgin Islands,
Caribbean,
Dominican Republic,
Jamaica,
Kid-Friendly Hotels,
Luxury Hotels,
Puerto Rico,
Punta Cana,
Romantic Hotels,
spring break,
St. Lucia,
Turks and Caicos,
Value Hotels,
Virgin Gorda

‘Tis the season for annual awards lists, but if you think you know what’s coming, guess again. Oyster’s awards aren’t like the other guys’ — we’re not like the other guys, so why should our awards be? You can find lists of the world’s best luxury hotels in a dozen other places, but only Oyster digs deep to learn every hotel’s secret quirks. Our hotel investigators trot the globe and visit every hotel in person so we can bring you the unvarnished truth, and this year, for the first-ever annual Oyster Hotel Awards, we’d like to show you the wackiest, coolest, weirdest, and most interesting things they came across in their travels. We are thrilled to present the 2012 selection of Oyster’s Most Interesting Hotels in the World. Are you ready for this?
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Boston,
Botswana,
British Virgin Islands,
Chicago,
Costa Rica,
Dominican Republic,
Finger Lakes,
Hong Kong,
Ireland,
Jamaica,
Las Vegas,
Lisbon,
Miami,
New York City,
Paris,
Rio de Janeiro,
Riviera Maya,
Rome,
San Diego,
San Francisco,
Sao Paulo,
Virgin Gorda
by Jane on November 29, 2012
Ahhhh. Numerous cottages have hammocks for lounging.
The Bitter End Yacht Club, snuggled into a steep hill on the scenic North Sound, is a relaxed, family-friendly resort. The tech-free rooms (no TVs or Wi-Fi here) feature stunning views from the balconies, and the sliding doors allows breezes to sweep through; some rooms do not have air-conditioning but most guests find they don’t miss it. Rooms are simple but feel up-to-date with bright comforters, sleek bathrooms, and comfy lounge chairs. The white-sand beaches at the hotel may be narrow, but they are still the highlight here, offering plenty of water sports. Families will likely enjoy the calm waters, the small kids’ club, and the outdoor movie theater, while couples can enjoy the gorgeous views and the solid restaurant options. Those looking for a more luxurious stay may want to consider the Biras Creek Resort, but the Bitter End is a great choice for those looking for a more laid-back option with an authentic island vibe. See more incredible photos after the jump or read our full review now»
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British Virgin Islands,
In the Spotlight
by Jane on October 1, 2012
Beach at Rosewood Little Dix Bay
The Rosewood Little Dix Bay is a luxury property with an absolutely gorgeous, jungle-meets-ocean setting on Virgin Gorda. It’s one of the most romantic spots on this sparsely populated island and it’s easy to see why. After all, if this shot of the sandy beach and turquoise waters doesn’t have you thinking loving thoughts, we’re not sure what will. To add to the romantic vibe, rooms have island-inspired decor with elegant wood furnishings, exposed stone walls, and wooden beams, and the acclaimed spa features beautiful views. But we’d be content just lying under the palm trees or a thatched umbrella on the sand. So as we say every week, sit back, relax, and soak in the goodness that is the Rosewood Little Dix Bay.
Tagged as:
Beach Hotels,
British Virgin Islands,
Luxury Hotels,
Monday Morning Ahhhh,
Virgin Gorda
by Jane on August 9, 2012
Pool at the Biras Creek Resort
The Biras Creek Resort is a rustic-luxe retreat with just 31 suites. It features two beaches — one calm, looking out to the North Sound, and the other slightly rocky (but just as gorgeous). Most suites do not have TVs, but guests get access to free Wi-Fi and bicycles, as well as a long list of on-site amenities: tons of water sports, tennis courts, an attractive pool, a game room, an on-site restaurant, and a small fitness center. Even when occupancy is at its height, the 140-acre resort feels quiet, giving it a tranquil, secluded vibe which is just why visitors come. See more incredible photos after the jump or read our full review now»
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Boutique Hotels,
British Virgin Islands,
In the Spotlight,
Luxury Hotels,
Virgin Gorda
Marina at the Bitter End Yacht Club
Some people plan summer road trips. For others, a summer adventure involves sailing or yachting on the high seas. But long boating trips are no fun without stopping to see the sights on land and stretching out your sea legs.
Luckily, these nine hotels, in beautiful locales ranging from the Caribbean to the Northeastern U.S., are situated right on marinas — so yachties can park and fuel up both their bodies and their boats. Some resorts, such as Hawks Cay Resort in the Florida Keys, let boaters sleep on board and still access all of the pools, restaurants, and activities on-site — all for no more than the docking fee.

Tagged as:
Bahamas,
British Virgin Islands,
Cabo San Lucas,
Florida Keys,
Luxury Hotels,
Miami,
The Hamptons
The Villa Montana Beach Resort; Aguadilla, Puerto Rico
What’s more relaxing than hearing the sound of the waves gently lapping against the fine golden sand while you snooze under a palapa? (Answer: Nothing. Duh.) Whether planning a family trip, a romantic tryst, or a long weekend away with friends, choosing the best beach is probably as important — or more — as booking the right hotel for your vacation. But nobody said it was easy to decide, with the many gorgeous options we’ve curated just for your (rainy day) viewing pleasure.

Tagged as:
Bahamas,
Barbados,
British Virgin Islands,
Cancun,
Costa Rica,
Dominican Republic,
Jamaica,
Miami,
Puerto Rico,
Turks and Caicos
Rosewood Little Dix Bay is a posh, romantic beach resort where lush greens are as abundant as is the white sand, thanks to the island’s jungle-to-beach terrain. And while most rooms virtually spill out onto the sand, some also come with dreamy extras like private pools, Wii game consoles and full kitchens. With the weather as gray and gloomy as it is today in New York City (we just saw lighting from our tenth floor HQ), we wanted to share a bit of the British Virgin Islands‘ sunny skies for your Monday a.m. goodness. So as we say every week, sit back, relax, and soak in the goodness that is the Rosewood Little Dix Bay.
Beach at Rosewood Little Dix Bay
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Tagged as:
British Virgin Islands,
Luxury Hotels,
Monday Morning Ahhhh,
Romantic Hotels,
Virgin Gorda