Greater Antilles Small Ship Cruises

Charlotte Amalie to San Juan

Charlotte Amalie to San Juan
7 Days from $2,999

Join this unique 7-day adventure from Charlotte Amalie to San Juan on the SeaDream II, with stops in the Virgin Islands and French Antilles. Explore undiscovered gems of the Caribbean as you sail this incredible region, enjoying adventure options and breathtaking views of the islands. Enjoy some of Saba's unspoiled beauty with a hike along the Crispeen Track

Central America & Cuba: Colon - Havana

Colon to Havana
15 Days from $9,275

Enjoy Central America and the Caribbean on this 15-day sailing adventure from Colon to Havana aboard your luxury sailing schooner the Sea Cloud II. Enjoy sandy beaches, explore marine animals and rainforest or simply be amazed at different UNESCO World Heritage Sites

Boston to Nassau
9 Days from $7,895

Zakim Bridge reflection on the Charles River in Boston

East Coast USA Adventure

Tracing more than 3,200 kilometers down the graceful eastern coast of the USA and into the shimmering Caribbean, this voyage is perfect for those who enjoy the stunning coastal scenery and alluring architecture.

Fort Lauderdale to Bridgetown

Fort Lauderdale to Bridgetown
11 Days from $4,700

Discover the Caribbean on this 11-day sailing adventure. Visit the colorful small cities and the exceptional beaches this archipelago is famous for as you sit back and relax while sailing one of the most exclusive regions in the world aboard the Silver Whisper.

During your 15-day cruise, board your luxurious ship in Miami and stop in the stunning Bahamas, then sail across the tropical Caribbean waters on your way to Saint George’s, and start your journey across the Atlantic Ocean visiting Azores and finally, the capital city of Lisbon, your port of disembarkation.

Board the Le Boreal for an amazing 15-day transatlantic voyage discovering the Bahamas, Bermuda and Azores archipelagos.

All Greater Antilles Luxury Tours

Best Luxury Small Ship Cruises of the Greater Antilles

During your 15-day cruise, board your luxurious ship in Miami and stop in the stunning Bahamas, then sail across the tropical Caribbean waters on your way to Saint George’s, and start your journey across the Atlantic Ocean visiting Azores and finally, the capital city of Lisbon, your port of disembarkation.

Fort Lauderdale to Bridgetown

Fort Lauderdale to Bridgetown
11 Days from $4,700

Discover the Caribbean on this 11-day sailing adventure. Visit the colorful small cities and the exceptional beaches this archipelago is famous for as you sit back and relax while sailing one of the most exclusive regions in the world aboard the Silver Whisper.

Board the Le Boreal for an amazing 15-day transatlantic voyage discovering the Bahamas, Bermuda and Azores archipelagos.

Greater Antilles Small Ship Cruises (7 Results)

Best Small Ship Cruises of the Greater Antilles

All Greater Antilles Small Ship Cruises

Galapagos Legend

With four decks, this cruise ship is one of the biggest boats in the Galapagos, offering plenty of amenities and features onboard, but still managing to balance that with a feeling of intimacy and proximity to the natural charms of the Islands. Guests enjoy a casual atmosphere, with only the highest standards of comfort and service.

These twin motor yachts will take you on an authentic Galapagos adventure in comfort and style. Panoramic windows, a sun deck, and a shadow deck allow you to experience the Islands in the most intimate way possible. Guests enjoy air- conditioned cabins with private bathrooms.

Corals

Named for Darwin's famous theory, the Evolution is a comfortable motor yacht ideal for families or travelers hoping to get in some diving on their Galapagos vacation. The itineraries focus on the natural experience and give you engaging ways to experience what the Islands' first explorers did centuries ago.

Evolution

Cruise the Galapagos Islands aboard the M/C Endemic, a glamorous catamaran that provides guests the style and comfort they need to have an adventure of a lifetime! The outer design is sleek, streamlined and attractive: the gentle curves of the hull and decks of the Endemic mimic the unique Galapagos ecosystem.

M/C Galapagos Endemic

Explore the Galapagos in one of the most elegant yachts in the Islands. This boat lives up to its prestigious name with both comfort and service, featuring a sun deck with a Jacuzzi, delicious meals served either inside or in the al fresco dining area, comfortable staterooms, & even a kids' area. Plus, the itineraries highlight the best of nature.

Grace

The twin sister boat of the Archipel I, this comfortable Galapagos catamaran offers 16 guests stability and comfort in its well appointed cabins and spacious social areas. A friendly crew, gourmet meals, and fun activities complement the luxurious suites, lounge, deck, and bar.

Cruise the Galapagos on the Archipell ship

Archipell II

Now known as the Journey I, this catamaran travels to the remote islands and features exciting activities. Guests will enjoy ample social areas both inside and out and well-furnished staterooms and suites. There is also a bar, lounge, and Jacuzzi for your relaxation whenever the ship is anchored.

Anahi

The beautiful EcoGalaxy is a new, eco-friendly Galapagos catamaran. Built in 2014, she provides leisurely excursions, optimal comfort, attentive guides, and upgraded, modern social areas. With capacity for just 16 passengers in 8 well-appointed cabins, this is an ideal vessel for your Galapagos cruise.

Cruise the Galapagos on the Galaxy II ship

EcoGalaxy

The Manatee Amazon Explorer is an intimate way to explore the great Amazon - it holds just 30 passengers, and is a stunning example of jungle comfort and luxury.

Manatee

The Cormorant is one of the most luxurious catamarans to sail the islands and has a well-earned reputation for top-notch service and excellent itineraries that visit the best spots in the Galapagos Islands.

Cormorant

Havana to Havana
7 Days from $3,490

Active Tours of the Greater Antilles

Cycling through the revolutionary landscape of Cuba

Cuba Multisport

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 countryside. Experience great colonial cities including Havana, Cienfuegos, Trinidad, and Sancti Spiritus. Discover Cuba's history, rich traditions, and dynamic present on this Cuba multisport trip.

Discover natural beauty and rich Cuban heritage on this 8-day People-to-People walking tour in Cuba. Visit Cienfuegos, Trinidad, Playa Larga, Vinales, Havana, and five parks & reserves. Explore by foot and encounter local experts, farmers, and artists as you gain insight into their history, traditions & vibrant culture on this highlights Cuba trip.

Cuba Walking Tour

8 Days from $3,490

Experience Cuba on a unique land and kayaking program. Discover three of Cuba’s greatest resources: its people, colorful culture, and natural wonders. In Havana, meet the artists, musicians, and historians who are preserving tradition. Explore great colonial cities and pristine marine & terrestrial habitats.

Cuba Kayaking West Tour

8 Days from $3,190

All Greater Antilles 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!

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.

Vintage car in Jose Marti Square, Cienfuegos, Cuba

Cuba FAQs