Have questions? We're here.

Greater Antilles Small Ship Cruises

Travel made your way
Clear waters of the Caribbean sea
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
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
All Greater Antilles Tours

Top 10 Small Ship Cruises of the Greater Antilles for 2023-2024

All Greater Antilles Tours

8 Best Small Cruise Ships of the Greater Antilles for 2023-2024

Ship NameMax PassengersFromSummary
Sea Cloud II94$4495The Sea Cloud II is a legendary windjammer comparable to her sister ship, the Sea Cloud. Featuring her own unique character, the Sea Cloud II …
Le Dumont-d'Urville184$6080Discover a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with …
Ocean Voyager202$3759Skillfully designed to foster a convivial atmosphere, the Ocean Voyager invites you to relax and unwind as you discover the world's most remarkable …
Silver Dawn596$4900Introducing the new luxury ship from Silversea, Silver Dawn, a combination of both the classic and modern evolution of their fleet that has the best …
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 …
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 …
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 …
Seabourn Quest450$40499Seabourn Quest is the third iteration of the vessel design that has been called ?a game-changer for the luxury segment.? True to her Seabourn …

Top 10 Active Tours of the Greater Antilles for 2023-2024

Trip NameFromDaysNext DepartureSummary
Boston, MA to Nassau, Bahamas$664916Nov 2, 2023On this 16-day journey along the United States' Atlantic Coast, board the Ocean Voyager. Sail from Boston, Massachusetts to Nassau, Bahamas. Explore …
Christmas Cuban Style$1029515Dec 21, 2023Board Sea Cloud II for this 15-day cruise from Santo Domingo, Dominican Republic to Havana, Cuba. Depart Santo Domingo and cruise to Port Antonio, …
The incomparable temperament of Cuba$729513Jun 4, 2023Board the Sea Cloud II to join this 13-day cruise from Havana to Cienfuegos. Stop in Maria la Gorda, Santiago de Cuba, and Port Antonio, Jamaica to …
The Rousing Rhythms of Cuba$736511Jan 15, 2023Board Sea Cloud II for this 11-day cruise from Havana to Santo Domingo. Visit the Cuban ports of Cienfuegos, Maria La Gorda, and Santiago de Cuba, …
Bahamas Sailing Adventure$14997Dec 4, 2022Board the luxurious sailing schooner Liberty Clipper in Nassau for a 7-day roundtrip cruise of the Bahamas, then explore the extensive Exumas …
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 …
Experience Firsthand the Festive Days in Cuba$999515Dec 21, 2022Board Sea Cloud II for this 15-day cruise from Havana to Santo Domingo. Visit the Cuban ports of Cienfuegos, Maria La Gorda, and Santiago de Cuba, …
Cuba Kayaking West Tour$31908Dec 4, 2022Experience Cuba on a unique land and kayaking program. Discover three of Cuba’s greatest resources: its people, colorful culture, and natural …
Cuba Multisport$34907Dec 1, 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 …
Cuba Walking Tour$31908Dec 4, 2022Discover natural beauty and rich Cuban heritage on this 8-day People-to-People walking tour in Cuba. Visit Cienfuegos, Trinidad, Playa Larga, …
All Caribbean Videos

Greater Antilles Videos

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.
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...
  • 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
  • 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 2023-2024
  • 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.


    Caribbean Travel Guide

    Favorite Caribbean All Trips

    Top Greater Antilles Travel Destinations

    Greater Antilles Trips by Departure Date

    Top Experiences in Greater Antilles

    Greater Antilles Trips by Duration

    Greater Antilles Trips by Activity

    More Reasons

    Why Travel With Adventure Life

    All News

    Recognized By