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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.

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.

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.

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.

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.

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.

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.

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.

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.

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.


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

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.

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.

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.

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.

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.

SKB - Robert Bradshaw International Airport

Saint 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.

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.

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.

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.

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.

STT - Cyril King Airport


Tours & Activities
Pre & Post Cruise
  • Hotel
    Moon Palace Jamaica – All Inclusive
  • Tours & Activities
    SoCoHo Half Day Jeep Safari- Mangrove Kayak & Reef Snorkeling
  • Pre & Post Cruise
    Bridgetown, Barbados
  • Hotel
    Secrets Royal Beach Punta Cana - Adults Only
  • Tours & Activities
    Waverunner Rentals
  • Pre & Post Cruise
    Oranjestad, Aruba
  • Hotel
    Breathless Punta Cana Resort & Spa -Adult Only
  • Tours & Activities
    Speedboat to Northern Exuma (Allans Cay, Sandbar, Normans Cay)
  • Pre & Post Cruise
    Philipsburg, St. Maarten
  • Hotel
    Secrets St. James Montego Bay - Luxury
  • Tours & Activities
    Mamma Gal Native Experience
  • Pre & Post Cruise
    San Juan, Puerto Rico
  • Hotel
    Secrets Wild Orchid Montego Bay - Luxury
  • Tours & Activities
    The Original Bridgetown Walking Tour
  • Pre & Post Cruise
    St. Thomas, USVI
  • Hotel
    OneandOnly Ocean Club
  • Tours & Activities
    Horseshoe Bay Beach Nature Trail Tour
  • Pre & Post Cruise
    Fort Lauderdale, Florida
  • Hotel
    Sandals Emerald Bay - ALL INCLUSIVE Couples Only
  • Tours & Activities
    Private Snuba Experience in Virgin Gorda
  • Pre & Post Cruise
    Monte Carlo, Monaco
  • Hotel
    Barceló Aruba - All Inclusive
  • Tours & Activities
    Stingraycity Adventure
  • Pre & Post Cruise
    Nice, French Riviera