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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.


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 the Anguilla

AXA - Clayton J. Lloyd International Airport


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 the Antigua

ANU - VC Bird International Airport
Featured Port City
Aruba’s brightly colored capital is filled with modern shops, upscale restaurants and colonial-era buildings.

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Bucuti Beach Resort and Tara Suites Gallery - Caribbean: Aruba - BBA


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 the Aruba

AUA - Queen Beatrix International Airport


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 the Bahamas

NAS - Nassau International Airport


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 the Barbados

BGI - Grantley Adams International Airport


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 the Bermuda

Exterior Destinations - Caribbean: Bermuda                - Exterior

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 the British Virgin Islands

EIS - Terrance Lettsome International Airport

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 the Cayman Islands

Exterior Destinations - Caribbean: Cayman Islands - Exterior


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 the Curacao

CUR - Hato International Airport

Dominican Republic

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

Hotels in the 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 the Grenada

GND - Grenada Airport


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 the Jamaica

MBJ - Sangster International Aiport


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 the Martinique

FDF - Lamentin International Airport

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 the Puerto Rico

SJU - Luis Munoz Marin International Airport

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 the St. Barthelemy

SBH - St Barthelemy Airport

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 the St. Kitts & Nevis

SKB - Robert Bradshaw International Airport

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 the St. Lucia

UVF - Hewanorra International Airport

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 the St. Martin

SXM - Princess Juliana International Airport

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 the St. Vincent & The Grenadines

CIW - Canouan Island Airport

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 the Turks & Caicos

PLS - Providenciales International Airport

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 the U.S. Virgin Islands

STT - Cyril King Airport


Tours & Activities
Pre & Post Cruise
  • Hotel
    Moon Palace Jamaica All Inclusive
  • Tours & Activities
    Walking Tour of Bridgetown Barbados
  • Pre & Post Cruise
    Bridgetown, Barbados
  • Hotel
    Secrets Royal Beach Punta Cana Adults Only All Inclusive
  • Tours & Activities
    Horseback Riding Adventure in Punta Cana
  • Pre & Post Cruise
    Oranjestad, Aruba
  • Hotel
    Breathless Punta Cana Resort & Spa
  • Tours & Activities
    Las Terrenas Scuba Diving Discovery Course
  • Pre & Post Cruise
    Philipsburg, St. Maarten
  • Hotel
    Secrets St. James Montego Bay Luxury All Inclusive
  • Tours & Activities
    Jamaica Dunn's River Falls Snorkel Cruise
  • Pre & Post Cruise
    San Juan, Puerto Rico
  • Hotel
    Secrets Wild Orchid Montego Bay
  • Tours & Activities
    Reggae Catamaran Negril Jamaica Sail N Snorkel
  • Pre & Post Cruise
    St. Thomas, USVI
  • Hotel
    The Ocean Club A Four Seasons Resort Bahamas
  • Tours & Activities
    Pelican Arts and Crafts Tour
  • Pre & Post Cruise
    Fort Lauderdale, Florida
  • Hotel
    Sandals Emerald Bay Great Exuma All Inclusive
  • Tours & Activities
    2-Hour Horseback Riding Adventure from Punta Cana
  • Pre & Post Cruise
    Monte Carlo, Monaco
  • Hotel
    Barceló Aruba
  • Tours & Activities
    2-Tank Dive Trip in Las Terrenas for Certified Divers
  • Pre & Post Cruise
    French Riviera, France