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Greater Antilles Small Ship Cruises

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Greater Antilles
  • 11 Cruises + Land Tours
Picturesque Cuba
Caribbean
  • 37 Cruises + Land Tours
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Clear waters of the Caribbean sea
Antigua
  • 8 Cruises
Lush green forests and clear blue waters of the Caribbean
Barbados
  • 14 Cruises
Take a leisurely stroll through beautiful Bridgetown
Dominica
  • 9 Cruises
Encounter tropical wildlife while you sail on the Aranui
Grenada
  • 10 Cruises
Snorkel the clear, tropical waters
Lesser Antilles
  • 29 Cruises
Wander the white-sand beaches of St. Johns on your Virgin Islands cruise
Netherlands Antilles
  • 4 Cruises
Enjoy a blissful snorkeling trip.
Puerto Rico
  • 1 Cruise
Discover incredible history and culture in Puerto Rico
Lesser Antilles
  • 29 Cruises
Wander the white-sand beaches of St. Johns on your Virgin Islands cruise
St. Barth
  • 7 Cruises
Play on the famously beautiful beaches of St. Barth's
St. Kitts
  • 4 Cruises
Stroll along the beautiful beaches of the Caribbean
St. Vincent des Grenadines
  • 11 Cruises
Visit beautiful St. Vincent
British Virgin Islands
  • 6 Cruises
Relax on the beaches of the Caribbean
U.S. Virigin Islands
View gorgeous sunsets over the Virgin Islands
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Breathe in the fresh island air of the Caribbean as you explore the Greater Antilles on a luxury small ship cruise. Charming Cuba invites travelers to enjoy myriad activities, from cigar sampling tours to cycling to walking tours of historic sites around the island like Havana and Bay of Pigs. From the tropical island paradise of Puerto Rico, discover the marine wonders of the Caribbean when you snorkel and dive in the reefs and visit the small towns that give these islands their character. Along the way, each small port and the tranquil beach is a perfect mix of cultural immersion, adventure, and relaxation for your Caribbean vacation. Let us know when you're ready to start planning your trip to the Greater Antilles. 
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Top 7 Small Ship Cruises of the Greater Antilles for 2022-2023

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Relax in the sunny squares of historic Savannah
Boston, MA to Nassau, Bahamas
Boston to Nassau
16 Days from $5,599
On this 16-day journey along the United States' Atlantic Coast, board the Ocean Voyager. Sail from Boston, Massachusetts to Nassau, Bahamas. Explore historic ports such as Newport, RI; Baltimore, MD; Wilmington, NC; Charleston, SC; and Savannah, GA aboard the Ocean Voyager.
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Enjoy a ride around the islands.
Bahamas Sailing Adventure
Nassau to Nassau
7 Days from $1,499
Board the luxurious sailing schooner Liberty Clipper in Nassau for a 7-day roundtrip cruise of the Bahamas, then explore the extensive Exumas archipelago and the Out Islands, including Eleuthera. Daily shore excursions include snorkeling, kayaking, and paddle boarding in crystal turquoise waters, or optional cultural and wildlife tours.
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Relax on the sunny beaches of the Bahamas
Exploring the Bahamas’ Out Islands: Natural Wonders & Hidden History
Great Exuma, Bahamas Roundtrip
8 Days from $5,590
A unique 8-day journey into the islands' remarkable culture & wildness. The Bahamas is truly wild at heart. This archipelago of more than 700 islands—of which only about 30 are inhabited—is home to blue holes and thick mangrove forests, coral reefs, and spectacular beaches.
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Relax on the beaches of the Caribbean
Christmas and New Year in the Caribbean
Fort-de-France - Santo Domingo
14 Days from $6,180
Spend an unforgettable festive season celebrating Christmas and New Year's in the Caribbean aboard Le Dumont-d'Urville. Cruise from Fort-de-France to Santo Domingo, exploring highlights such as Martinique, Dominica, Antigua and Barbuda, St. Kitts, Saint Barthelemy, and the British Virgin Islands along the way.
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Caribbean
Philipsburg Round Trip
Philipsburg to Philipsburg
8 Days from $4,925
Join the Sea Cloud Spirit on a roundtrip Caribbean cruise to St. Maarten which includes stops in Puerto Rico, the British Virgin Islands, and France. The British and US Virgin Islands are a true dream vacation, with over 100 islands and riffs, most of which are uninhabited. This paradise attracts sailing enthusiasts from all over the world.
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Explore colorful Gustavia
Santo Domingo and Caribbean treasures
Santo Domingo - Fort-de-France
13 Days from $5,440
From Santo Domingo to Fort-de-France, succumb to the charms of the Caribbean aboard a new 13-day cruise. Swimming and spectacular discoveries await in the Antilles aboard the Le Dumont-d'Urville.
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Visit historic Baltimore
Boston, MA to Nassau, Bahamas
Boston to Nassau
16 Days from $5,599
Join the Ocean Navigator on a 16-day journey down the Atlantic Coast of the United States. Sail to Nassau, Bahamas, from Boston, Massachusetts. Visit historic ports such as Newport, RI, Baltimore, MD, Wilmington, NC, Charleston, SC, and Savannah, GA.
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6 Best Small Cruise Ships of the Greater Antilles for 2022-2023

Ship NameMax PassengersFromSummary
Le Dumont-d'Urville184$5440Discover a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with …
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Sea Cloud Spirit136$4925Sea Cloud Spirit is a modern and elegant windjammer with occupancy for 136 guests and a crew of 85. It gives you an amazing opportunity of traveling …
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Ocean Voyager202$4699Skillfully designed to foster a convivial atmosphere, the Ocean Voyager invites you to relax and unwind as you discover the world's most remarkable …
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Liberty Clipper24$1499The Liberty Clipper is a 125-foot beautifully renovated gaff-rigged schooner, a replica of the renowned Baltimore Clippers, made famous over a …
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Ocean Navigator202$5599Perfectly designed spaces for every mood and every possibility the Ocean Navigator takes you on a splendid sailing discovery of some of the most …
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National Geographic Sea Lion62$5590The Sea Lion, sister ship of the Sea Bird, can reach places inaccessible to larger ships due to its small size, yet it comfortably accommodates 62 …
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All Greater Antilles Deals

1 Greater Antilles Travel Deals for 2022-2023

Trip NameSaveFromDaysNext DepartureSummary
Boston, MA to Nassau, BahamasSavings$559916Nov 3, 2022Join the Ocean Navigator on a 16-day journey down the Atlantic Coast of the United States. Sail to Nassau, Bahamas, from Boston, Massachusetts. Visit …
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Top 10 Active Tours of the Greater Antilles for 2022-2023

Trip NameFromDaysNext DepartureSummary
Boston, MA to Nassau, Bahamas$559916Oct 27, 2022On this 16-day journey along the United States' Atlantic Coast, board the Ocean Voyager. Sail from Boston, Massachusetts to Nassau, Bahamas. Explore …
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Bahamas Sailing Adventure$14997Nov 20, 2022Board the luxurious sailing schooner Liberty Clipper in Nassau for a 7-day roundtrip cruise of the Bahamas, then explore the extensive Exumas …
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Exploring the Bahamas’ Out Islands: Natural Wonders & Hidden History$55908Dec 29, 2022A unique 8-day journey into the islands' remarkable culture & wildness. The Bahamas is truly wild at heart. This archipelago of more than 700 …
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Cuba Kayaking West Tour$31908Oct 2, 2022Experience Cuba on a unique land and kayaking program. Discover three of Cuba’s greatest resources: its people, colorful culture, and natural …
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Cuba Multisport$34907Nov 6, 2022Explore the intriguing island of Cuba on this active 7-day People-to-People multisport tour. Bike, hike, and kayak wild coastal sites and tranquil …
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Cuba Walking Tour$31908May 22, 2022Discover natural beauty and rich Cuban heritage on this 8-day People-to-People walking tour in Cuba. Visit Cienfuegos, Trinidad, Playa Larga, …
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Classic Cuba$22455May 22, 2022Rolled cigars, rum spiked with sugarcane juice, and colorful vintage cars - these are the icons of Cuba that await you on this 5-day People-to-People …
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Christmas and New Year in the Caribbean$618014Dec 23, 2022Spend an unforgettable festive season celebrating Christmas and New Year's in the Caribbean aboard Le Dumont-d'Urville. Cruise from Fort-de-France to …
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Philipsburg Round Trip$49258Nov 28, 2022Join the Sea Cloud Spirit on a roundtrip Caribbean cruise to St. Maarten which includes stops in Puerto Rico, the British Virgin Islands, and France. …
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Santo Domingo and Caribbean treasures$544013Jan 4, 2023From Santo Domingo to Fort-de-France, succumb to the charms of the Caribbean aboard a new 13-day cruise. Swimming and spectacular discoveries await …
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Greater Antilles Travel Guide

What to Know About the Greater Antilles
The Greater Antilles are the largest of the Caribbean Islands, including:
  • Cuba
  • Hispaniola (home to Haiti & the Dominican Republic)
  • Puerto Rico
  • Jamaica
  • Cayman Islands
A number of languages are spoken throughout the Greater Antilles, most with roots in the region's colonial history, including English, Spanish, French, and variations of Creole.

Although it is one geographic region, the cultures of the Greater Antilles are extremely diverse, with different native dishes, religious beliefs, customs, and traditions. Each island is home to its own distinct culture that you will get to know on our tours. 

Are the Greater Antilles part of the West Indies?
The Greater Antilles are part of three major archipelagos that comprise the West Indies, along with the Lesser Antilles and the Lucayan Archipelago.
Snorkel and dive in the clear waters of the Caribbean
Caribbean Island Guide
The Caribbean is so much more than sun, sand & surf. Various islands allow travelers to sample regional flavor & local adventures. The close proximity to the U.S. makes the Caribbean a perfect destination for a getaway. Get acquainted with some highlights of specific islands to plan a trip that is perfectly suited for you!
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Highlights of the Greater Antilles
Snorkeling in crystal clear waters, exploring colonial cities, and witnessing diverse wildlife are key parts of every tour. Additionally, some highlights of each island are...
Cuba
  • Stroll the famed Malecon promenade in historic old Havana
  • Snorkel and swim the clear waters of Maria la Gorda
  • Explore the beautiful old town of Cienfuegos
Jamaica
  • Visit banana and sugar plantations near Port Antonio, Jamaica
Dominican Republic
  • Marvel at historic Santo Domingo, the oldest city in the New World
Puerto Rico - Although Puerto Rico is technically a U.S. island territory and not part of the Greater Antilles, many cruises visit popular sites here like San Juan & Culebrita Island.
Enjoy the beautiful blue Caribbean
The Best Time to Visit the Greater Antilles
The Greater Antilles are a group of islands in the Caribbean, most prominently consisting of Cuba, Puerto Rico, Hispaniola, and Jamaica. The Greater Antilles are warm year-round and always welcoming to tourists- except for June through September as this is the hurricane season when, generally, these islands should be avoided.
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Vintage car in Jose Marti Square, Cienfuegos, Cuba
Cuba FAQs
Planning a trip to Cuba? Now what? From the best time to visit to entry requirements, this FAQ gives travelers more of an idea of what to expect on a trip to Cuba. We have answered some of the most common traveler questions in hopes of helping you feel better prepared for the adventure.
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Best Greater Antilles Small Ship Cruise Lines for 2022-2023
  • Ponant - strives to provide a personalized cruise experience, working diligently to provide you with first-class, intuitive service. Le Dumont-d'Urville cruises the Greater Antilles' gorgeous white-sand beaches and crystalline waters fringed by palm trees.
  • Silversea Cruises - has a fleet of small ships that can access ports where larger vessels cannot. This means its diversified, hand-picked itineraries have the perfect balance of iconic destinations and hidden gems. Silver Wind not only takes you to the best islands in the Greater Antilles, but with a staff-to-guest ratio of almost 1:1, it takes you there in style.
  • American Queen Voyages - ventures off the beaten road to uncover North America's unscripted adventures, sailing through the state of Florida, the closest point on the U. S. mainland to the Greater Antilles. Ocean Voyager and Ocean Navigator offer small-ship cruising with immersive shore excursions and onboard programs aboard similar 202-passenger ships.


 

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