Anguilla

For those seeking a truly decadent escape, the Caribbean is certainly not short on options. The islands boast everything from intimate boutiques in hidden, tranquil locales to expansive resorts that wow not only in breadth, but style. These super-luxe properties cater to celebrities and socialites — and you can enjoy them too (for a price, of course — or at least just in pictures). Spoil yourself with these 13 uber-fancy spots!

1. Hotel Le Toiny, St. Barts 

toiny

One of the most prestigious hotels in St. Barts, this exclusive 15-villa resort sits amid 28 lush acres of natural hills and beachfront. The private villas are spacious and airy, and each boasts its own infinity-edge pool. Plus, the views here are jaw-dropping. The French restaurant is one of the island’s most renowned, and you can often spot a celebrity dining during high season. Rates are nothing to sneeze at, but you’ll definitely receive all-star treatment. Read More »

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The perks of the megaresort experience are obvious: free-flowing drinks, lots of chances to socialize with your fellow guests, and a sweeping breadth of amenities. But with these advantages comes an obvious lack of peace and quiet. When all you want to do is escape the crowds, the best bet is to seek out the small, hidden properties dotting the Caribbean shores. From eco-centric boutiques to romantic enclaves, these laid-back properties promise the glorious sound of silence. So sit back, relax, and enjoy these crowdless Caribbean locales.

Anacaona Boutique Hotel, Anguilla 

anguilla

Anguilla, a small British territory in the Caribbean, spans fewer than 40 square miles. Less built up than other isles, it manages to exude both an upscale and happy-go-lucky vibe with its gorgeous white-sand beaches and turquoise waters. There are few attractions, so days will mostly be spent sipping on drinks beach-side and dining at one the island’s exclusive hotels. The 27-room Anacaona, for example, offers access to a stunning stretch of sand, rounds of golf at the nearby Greg Norman-designed course, dinner at a great restaurant serving Caribbean fare with a twist, and a massage hut on the beach. The hotel is a great choice for rest and relaxation–and it’s an excellent value to boot. Read More »

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For true foodies, a vacation that doesn’t involve mouth-watering cuisine is hardly worthy of the title. In fact, food can often be a major focus of a trip; it’s hardly uncommon for the taste connoisseurs among us to plan a foodcation. And in our opinion, it should all start with your hotel. If you stay somewhere with a truly phenomenal restaurant right on the premises, your foodcation will be off to a wonderful start. Whether you’re heading to New York City for its famous fine dining, California wine country for its earthy farm-to-table fare, or Mexico for an elaborate upscale meal on the beach, we’ve got a first-rate foodie hotel for you. Take a look at the top hotel restaurants we’d travel for in the U.S., Mexico, and Caribbean.

Dry Creek Kitchen at the Hotel Healdsburg, California

Dry Creek Kitchen at the Hotel HealdsburgCharlie Palmer’s Dry Creek Kitchen is one of the best – and best-known – restaurants in the Sonoma area, and for good reason. The farm-to-table, seasonal menu features items such as California Sea Bass with sweet corn fondue and Sonoma County Liberty Duck with crispy sunchokes. The restaurant’s outdoor terrace is situated under a shady arbor. Read More »

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Who doesn’t love a beach vacation? The sun, the sand, and the ocean all come together to make for a relaxing getaway that, when complete, will send you home rested and relaxed – and hopefully with a tan! Where you stay, however, can make a big difference on just how fabulous your beach trip is. That’s why we’ve found the 15 most decadent hotels on the sand to ensure that you enjoy the ultimate beachfront luxury.

Eden Roc at Cap Cana, Dominican Republic

Eden Roc at Cap Cana

The Eden Roc, opened in 2012, is one of the most high-tech properties in the Dominican Republic, and is located in the gated Cap Cana community — which has a Jack Nicklaus-designed golf course, marina, and beach club. The 34 colorful suites are clustered around a small, man-made lagoon and feature elegant decor (picture four-poster beds, intricate floor tiling, and spacious bathrooms). Up-to-date amenities include iPad-controlled lights, sound systems, and TVs with numerous channels in Spanish and English. Suites also come with small pools and golf carts for getting around the property.
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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.

Anacaona Boutique Hotel, 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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While there are many great budget-friendly hotels in the Caribbean, the islands are also known for their luxury properties, where guests are treated to day trips aboard yachts, couples are offered massages in sumptuous spas, and rooms are twice the size of a New York apartment (although, we guess it’s not too hard to be). We’ve compiled a list of our favorite luxury hotels in the Caribbean so you can start planning what to do after your new year’s resolution of winning the lottery (that’s not a new year’s resolution, but, really, who hasn’t had that on the list for at least a decade?) comes true.

One&Only Ocean Club – Bahamas

All guests have a butler on call 24/7 assigned to their room upon arrival.

All guests have a butler on call 24/7 assigned to their room.

Bringing tranquility to otherwise-crowded Paradise Island, the 105-room Ocean Club’s personal butlers, beautiful pools (one for adults, one for families), restaurant from Jean-Georges, and access to Atlantis’s water park, casino, and other attractions make it one of the Caribbean’s best resorts.

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Water doesn't get much prettier than that!

The 27-room Anacaona is a solid mid-range option in Anguilla’s West End — and for a beach like that, we’d stay just about anywhere! 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-designed golf course and a few restaurants. Rooms are large and airy, and have great amenities, including large flat-screen TVs with dozens of channels, iPod docks, free Wi-Fi, and Frette linens. With two small pools, free snorkeling equipment, a great restaurant serving Caribbean fare with a twist, and a massage hut on the beach, the hotel is a good pick for value. So as we say every week: sit back, relax, and soak up the goodness that is the Anacaona Boutique Hotel.

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