Caribbean - Vacation Getaways

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.

The Regions 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.

Hotels in Anguilla

Cap Juluca - JUL

CuisinArt Golf Resort & Spa - CSN

Four Seasons Resort Anguilla and Residences - VCE

> View All Hotels in Anguilla


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.

Hotels in Antigua

Carlisle Bay - CBA

Hermitage Bay Antigua - HEB

Sandals Grande Antigua Resort & Spa - SAR

> View All Hotels in Antigua


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

Hotels in Aruba

Aruba Marriott Resort and Stellaris Casino - MRC

Bucuti & Tara Beach Resorts - BBA

The Westin Resort & Casino, Aruba - WAB

> View All Hotels in Aruba


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

Hotels in Bahamas

The Cove Atlantis - APC

The Reef Atlantis - RFA

Sandals Emerald Bay Golf, Tennis and Spa Resort - SEB

One&Only Ocean Club - TOC

> View All Hotels in Bahamas


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.

Hotels in Barbados

The Fairmont Royal Pavilion, Barbados - ROY

Cobblers Cove - COB

The Crane Residential Resort - CRN

> View All Hotels in Barbados


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.

Hotels in Bermuda

Hamilton Princess & Beach Club, Bermuda - PRH

Fairmont Southampton - SPR

> View All Hotels in Bermuda

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.

Hotels in British Virgin Islands

Scrub Island Resort, Spa & Marina, Autograph Collection - SCB

Peter Island Resort & Spa - PRY

Bitter End Yacht Club - BIT

> View All Hotels in British Virgin Islands

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.

Hotels in Cayman Islands

The Ritz-Carlton, Grand Cayman - RGC

Caribbean Club Cayman, Seven Mile Beach - CCL

> View All Hotels in Cayman Islands


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.

Hotels in Curacao

Baoase Luxury Resort - BAO

Avila Hotel Curaçao - AVH

> View All Hotels in Curacao

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.

Hotels in Dominican Republic

Zoëtry Paraiso de la Bonita Riviera Maya - PDB

Breathless Punta Cana Resort & Spa - BPS

> View All Hotels in Dominican Republic


Known as the "spice" of the Caribbean, Grenada, Carriacou and Petite Martinique is a place full of lively people, sights and sounds.

Hotels in Grenada

Spice Island Beach Resort - SIB

Sandals LaSource Grenada Resort and Spa - SLG

> View All Hotels in Grenada


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

Hotels in Jamaica

Moon Palace Jamaica Grande - MPJ

Secrets Wild Orchid Montego Bay - WLD

> View All Hotels in Jamaica


Famous for its spectacular beaches, smoldering volcano and unparalleled French-Caribbean elegance, Martinique offers the luxury traveler a wide range of unforgettable experiences.

Hotels in Martinique

Le Cap Est Lagoon Resort & Spa - LEC

MGallery Bakoua Martinique - BAK

> View All Hotels in Martinique

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.

Hotels in Puerto Rico

Las Casitas Village, A Waldorf Astoria Resort - LCV

W Retreat & Spa, Vieques Island, Puerto Rico - WQS

Dorado Beach, a Ritz-Carlton Reserve - RRP

> View All Hotels in Puerto Rico

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.

Hotels in St. Barthelemy

Eden Rock - St Barths - EDR

Le Guanahani - GUA

> View All Hotels in St. Barthelemy

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.

Hotels in St. Kitts & Nevis

St. Kitts Marriott Resort & The Royal Beach Casino - MSK

Four Seasons Resort Nevis - FRN

> View All Hotels in St. Kitts & Nevis

St. Lucia

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

Hotels in St. Lucia

Sandals Regency La Toc Golf Resort & Spa - SLR

Sandals Grande St. Lucian Spa & Beach Resort - SGS

Ti Kaye Resort & Spa - TKI

> View All Hotels in St. Lucia

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.

Hotels in St. Martin

Belmond La Samanna Villas - VSL

Radisson Blu Resort, Marina & Spa St. Martin - RAD

> View All Hotels in St. Martin

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.

Hotels in St. Vincent & The Grenadines

Palm Island Resort - PIR

> View All Hotels in St. Vincent & The Grenadines

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.

Hotels in Turks & Caicos

Beaches Turks & Caicos Resort Villages & Spa - BTC

The Palms Turks and Caicos - PMS

> View All Hotels in Turks & Caicos

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.

Hotels in U.S. Virgin Islands

The Ritz-Carlton, St. Thomas - RCS

The Westin St. John Resort & Villas - WSJ

Buccaneer Hotel & Golf Course - BUC

Frenchman's Reef & Morning Star, Marriott Beach Resort - MFR

> View All Hotels in U.S. Virgin Islands

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