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


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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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 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
Occidental Grand Aruba
Bucuti & Tara Beach Resort

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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
The Cove Atlantis
The Reef Atlantis
Atlantis Beach Tower, Paradise Island
Atlantis Coral Towers, Paradise Island
Atlantis Royal Towers, Paradise Island

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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
The Crane Residential Resort
Cobblers Cove

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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
Hamilton Princess & Beach Club, A Fairmont Managed Hotel
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 & Spa
Bitter End Yacht Club
Scrub Island Resort, Spa & Marina, Autograph Collection

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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
Caribbean Club Cayman, Seven Mile Beach

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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
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
Dreams Punta Cana Resort & Spa
Dreams La Romana Resort & Spa
Dreams Palm Beach Punta Cana
NOW Larimar Punta Cana
Hard Rock Hotel and Casino, Punta Cana
Nickelodeon Hotel, Punta Cana by Karisma

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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
Sandals LaSource Grenada Resort and Spa

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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 – A Spa, Golf & Waterpark Resort
Beaches Negril Resort & Spa
Hyatt Ziva Rose Hall
Hyatt Zilara Rose Hall

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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 Martinique
Le Cap Est Lagoon Resort & Spa

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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 Village, A Waldorf Astoria Resort
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
Eden Rock - St Barths
Le Guanahani

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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 Regency La Toc Golf Resort & Spa
Sandals Grande St. Lucian Spa & Beach Resort
Ti Kaye 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
Belmond La Samanna
Belmond La Samanna Villas

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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

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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
The 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
Frenchman's Reef Marriott & Morning Star Beach Resort
Buccaneer Hotel & Golf Course

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