Top 10 Small Ship Cruises of the Greater Antilles for 2022-2023

Relax in the sunny squares of historic Savannah

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.

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.

Bahamas Sailing Adventure

Nassau to Nassau
7 Days from $1,399

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.

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.

Southern Coastal Charm

Roundtrip Amelia Island
12 Days from $4,699

Discover the charm of the Southern US coast on this 12-day cruise, round-trip from Amelia Island, Florida. Explore historic cities, beautiful sea islands, and the glittering beaches of the Bahamas on this unforgettable voyage aboard Ocean Voyager.

Philipsburg Round Trip

Philipsburg to Philipsburg
8 Days from $5,350

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.

Bridgetown to Fort Lauderdale

Bridgetown to Fort Lauderdale
9 Days from $4,140

Experience the Caribbean as never before on this 9-day cruise from Bridgetown to Fort Lauderdale aboard the luxurious Silver Wind. Visit stunning ports of Union, Grenadines, Dominica, Antigua & Barbuda, Virgin Gorda, and the Bahamas.

San Juan to Charlotte Amalie

San Juan to Charlotte Amalie
5 Days from $1,999

Board SeaDream II on this exclusive 5-day adventure sailing across the Caribbean and discover all the picture-perfect views that make this region famous.

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.

Boston, MA to Nassau, Bahamas

Boston to Nassau
16 Days from $5,599

Board Ocean Navigator on this 16-day cruise along the Atlantic Coast of the United States. Sail from Boston, Massachusetts to Nassau, Bahamas. Along the way, explore historic ports such as Newport, RI; Baltimore, MD; Wilmington, NC; Charleston, SC; and Savannah, GA.

7 Best Small Cruise Ships of the Greater Antilles for 2022-2023

Ship Name	Max Passengers	From	Summary
Le Dumont-d'Urville	184	$5440	Discover a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with … 0
Sea Cloud Spirit	136	$5350	Sea 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 … 0
Ocean Voyager	202	$4699	Skillfully designed to foster a convivial atmosphere, the Ocean Voyager invites you to relax and unwind as you discover the world's most remarkable … 0
Ocean Navigator	202	$5599	Perfectly designed spaces for every mood and every possibility the Ocean Navigator takes you on a splendid sailing discovery of some of the most … 0
National Geographic Sea Lion	62	$5590	The 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 … 0
Liberty Clipper	24	$1399	The Liberty Clipper is a 125-foot beautifully renovated gaff-rigged schooner, a replica of the renowned Baltimore Clippers, made famous over a … 0
Silver Wind	254	$4140	Discover Silver Wind's tranquility, sophistication, and genuine elegance. This multi-million dollar refit transforms her into one of the most … 0

Top 10 Active Tours of the Greater Antilles for 2022-2023

Trip Name	From	Days	Next Departure	Summary
Boston, MA to Nassau, Bahamas	$5599	16	Oct 27, 2022	On this 16-day journey along the United States' Atlantic Coast, board the Ocean Voyager. Sail from Boston, Massachusetts to Nassau, Bahamas. Explore … 0
Exploring the Bahamas’ Out Islands: Natural Wonders & Hidden History	$5590	8	Feb 20, 2022	A unique 8-day journey into the islands' remarkable culture & wildness. The Bahamas is truly wild at heart. This archipelago of more than 700 … 0
Bahamas Sailing Adventure	$1399	7	Jan 23, 2022	Board the luxurious sailing schooner Liberty Clipper in Nassau for a 7-day roundtrip cruise of the Bahamas, then explore the extensive Exumas … 0
Cuba Kayaking West Tour	$3190	8	Jan 23, 2022	Experience Cuba on a unique land and kayaking program. Discover three of Cuba’s greatest resources: its people, colorful culture, and natural … 0
Cuba Multisport	$3490	7	Jan 30, 2022	Explore the intriguing island of Cuba on this active 7-day People-to-People multisport tour. Bike, hike, and kayak wild coastal sites and tranquil … 0
Cuba Walking Tour	$3190	8	Jan 23, 2022	Discover natural beauty and rich Cuban heritage on this 8-day People-to-People walking tour in Cuba. Visit Cienfuegos, Trinidad, Playa Larga, … 0
Classic Cuba	$2245	5	Jan 20, 2022	Rolled 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 … 0
Christmas and New Year in the Caribbean	$6180	14	Dec 23, 2022	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 … 0
Southern Coastal Charm	$4699	12	Feb 10, 2022	Discover the charm of the Southern US coast on this 12-day cruise, round-trip from Amelia Island, Florida. Explore historic cities, beautiful sea … 0
Philipsburg Round Trip	$5350	8	Nov 28, 2022	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. … 0

All Caribbean Articles

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!

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.

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.

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.

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.