Caribbean Vacations

Throw on your sandals and enjoy the clean beaches, golf, inventive cuisine, and luxury resorts that define a Caribbean vacation. Classic Vacations can help you with your Caribbean travel plans by offering you the best Caribbean vacation packages and special offers available.

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The Islands of Caribbean

Anguilla

Stretch out on Anguilla’s beaches, soft as powder and nearly as white. You’ll find three of our exclusive Caribbean resorts here, plus cuisine to gratify gourmets. Learn More

Hotels in Anguilla
CuisinArt Golf Resort & Spa
Cap Juluca
Viceroy Anguilla

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Antigua

Warm waters and superb undersea visibility in the coral reefs make Antigua a magnet for water sports lovers who want the best Caribbean vacation experience. Learn More

Hotels in Antigua
Sandals Grande Antigua Resort & Spa
Carlisle Bay
Hermitage Bay Antigua

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Aruba

Aruba is a warm and welcoming island with shipwreck diving, snorkeling, casinos, golf, historic gold mines, and shopping as some of the highlights. Learn More

Hotels in Aruba
The Westin Resort & Casino, Aruba
Bucuti Beach Resort & Spa
Aruba Marriott Resort and Stellaris Casino

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Bahamas

From Nassau, bustling with luxury resorts, casinos and duty-free shopping to the quiet Out Islands, make the Bahamas your next Caribbean vacation destination. Learn More

Hotels in Bahamas
Sandals Royal Bahamian Spa Resort & Offshore Island
The Cove Atlantis
Sandals Emerald Bay, Great Exuma, Bahamas

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Barbados

Expect balmy weather, beautiful beaches, a wildlife preserve and botanical gardens; home to some of the best Caribbean resorts and where luxury and nature collide. Learn More

Hotels in Barbados
The Fairmont Royal Pavilion, Barbados

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Bermuda

It’s tee time on Bermuda, with more golf courses per square mile than any other country. Experience a Caribbean vacation filled with sun, swimming, and sailing. Learn More

Hotels in Bermuda
The Fairmont Hamilton Princess
The Fairmont Southampton

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British Virgin Islands

Sixty small islands surrounded by the topaz sea comprise the British Virgin Islands; for those seeking a great yachting experience on their Caribbean vacation. Learn More

Hotels in British Virgin Islands
Peter Island Resort and Spa
Bitter End Yacht Club

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Cayman Islands

Take a captivating Caribbean vacation on the Cayman Islands. The coral reefs offer some of world’s best locales for viewing underwater life and sunken ships. Learn More

Hotels in Cayman Islands
The Ritz-Carlton, Grand Cayman
Caribbean Club Cayman, Seven Mile Beach
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Grand Cayman Marriott Beach Resort

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Curacao

With dozens of white sand beaches and stunning coral reefs, Curacao is an ideal place for sun worshipers and divers to spend an unforgettable Caribbean vacation. Learn More

Hotels in Curacao
Avila Hotel Curaçao
Baoase Luxury Resort

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Dominican Republic

In the Dominican Republic, your Caribbean vacation can include golf, tennis, spas, horseback riding on the beach and even major league baseball practices. Learn More

Hotels in Dominican Republic
Paradisus Palma Real Golf & Spa Resort
Paradisus Punta Cana Resort

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Grenada

Known as the "spice" of the Caribbean, Grenada, Carriacou and Petite Martinique is an area full of lively people, sights and sounds. Learn More

Hotels in Grenada
Spice Island Beach Resort

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Jamaica

The endless array of beauty in Jamaica includes sugar-sand beaches, rivers, waterfalls, and the dense Blue Mountains that will entice the outdoor adventurer. Learn More

Hotels in Jamaica
Beaches Ocho Rios Resort & Golf Club
Beaches Negril Resort & Spa

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Martinique

Famous for its spectacular beaches, smoldering volcano and unparalleled French-Caribbean elegance, Martinique offers travelers a wide range of experiences. Learn More

Hotels in Martinique
MGallery Bakoua

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Puerto Rico

There’s no passport required for U.S. citizens to enjoy a Puerto Rico vacation filled with golf, dining, shopping, casinos and 272 miles of Caribbean coastline. Learn More

Hotels in Puerto Rico
Las Casitas Resort, The Waldorf Astoria Collection
W Retreat & Spa, Vieques Island, Puerto Rico

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St. Barthelemy

St. Barts is a favorite among celebrities and high-profile types. Experience a luxury Caribbean vacation on secluded beaches where you'll find privacy and relaxation. Learn More

Hotels in St. Barthelemy
Le Sereno
Hotel Guanahani & Spa

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St. Kitts & Nevis

Quiet and unspoiled, take a Caribbean vacation on these tiny islands where you can kick off your sandals on the beach and relax in 79 degree weather year-around. Learn More

Hotels in St. Kitts & Nevis
St. Kitts Marriott Resort & The Royal Beach Casino
Four Seasons Resort Nevis

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St. Lucia

Spend your luxury Caribbean vacation visiting the Piton Mountains in St. Lucia, a tropical rainforest with a waterfall that changes colors and a drive-in volcano. Learn More

Hotels in St. Lucia
Sandals La Toc Golf Resort & Spa in St. Lucia
Sandals Grande St. Lucian Spa & Beach Resort
Ti Kaye Village Resort & Spa

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St. Martin

Whether it’s St. Martin or St. Maarten, this island provides an unforgettable Caribbean vacation. St. Maarten is more touristy, but both boast fine beaches. Learn More

Hotels in St. Martin
La Samanna, an Orient Express Hotel
Radisson St. Martin Resort, Marina & Spa

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St. Vincent & The Grenadines

Set course for a Caribbean vacation in St. Vincent and the Grenadines. Experience coves formed by jagged coastlines and secluded beaches for ultimate privacy. Learn More

Hotels in St. Vincent & The Grenadines
Palm Island Resort
Buccament Bay

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Turks & Caicos

Turks and Caicos attracts scuba divers, snorkelers, and sports-fishing enthusiasts. The 200-mile-long coral reef – the world’s third largest—is the highlight. Learn More

Hotels in Turks & Caicos
Regent Palms Turks and Caicos
Beaches Turks & Caicos Resort Villages & Spa

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U.S. Virgin Islands

A superlative shopping district with two of the top ten beaches in the United States. Explore hidden coves and tropical forests on this Caribbean vacation. Learn More

Hotels in U.S. Virgin Islands
The Westin St. John Resort & Villas
The Ritz-Carlton, St. Thomas
Frenchman's Reef Marriott & Morning Star Beach Resort
Buccaneer Hotel & Golf Course

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