Top 10 Small Ship Cruises of the Greater Antilles for 2020-2021

Cienfuegos to Santo Domingo
10 Days from $8,935

Board Sea Cloud II for this 10-day Caribbean cruise from Cienfuegos, Cuba to Santo Domingo, Dominican Republic. Enjoy the rich musical culture of Santiago de Cuba, visit sugar and banana plantations around Port Antonio, Jamaica, and marvel at preserved Taino art in La Romana, Dominican Republic.

Havana to Cienfuegos

Havana to Cienfuegos
11 Days from $7,365

Board the Sea Cloud II to join this 11-day cruise from Havana to Cienfuegos. Stop in Maria la Gorda, Santiago de Cuba, and Port Antonio, Jamaica to explore some of the highlights of this region, interspersed with relaxing days at sea. Get a glimpse of the local history, culture, and lifestyle of Cuba.

Havana to Santo Domingo

Havana to Santo Domingo
13 Days from $7,975

Board Sea Cloud II for this 13-day cruise from Havana to Santo Domingo. Visit the Cuban ports of Cienfuegos, Maria La Gorda, and Santiago de Cuba, and the Jamaican city of Port Antonio, on your way to the Dominican Republic.

Santo Domingo to Havana

Santo Domingo to Havana
11 Days from $7,365

Board Sea Cloud II for this 11-day cruise from Santo Domingo, Dominican Republic to Havana, Cuba. Depart Santo Domingo and cruise to Port Antonio, Jamaica as well as several ports in Cuba, including Cienfuegos, Maria La Gorda, and Santiago de Cuba. End your journey in the vibrant Cuban capital, Havana.

Caribbean: Philipsburg to Havana

Philipsburg to Havana
15 Days from $9,265

Board the Sea Cloud II for this 15-day Caribbean cruise. Depart Philipsburg, St. Maarten to visit sparkling St. Barths; Santo Domingo, the oldest city in the New World; and sugar and banana plantations near Port Antonio, Jamaica. Cruise to Cuba to visit ports such as Cienfuegos and Maria la Gorda before departing from Havana.

San Juan to San Juan

San Juan to San Juan
8 Days from $4,899

Be a part of this magical 8-day adventure aboard the SeaDream ll. Starting and ending in San Juan, Puerto Rico, this cruise visits the most popular spots of the region. Sail through the Caribbean and discover the enchanting and exclusive islands of this perfect archipelago.

Philipsburg Round Trip

Philipsburg to Philipsburg
8 Days from $4,545

Join the Sea Cloud Spirit on its 8-day Caribbean cruise to St. Maarten, Puerto Rico, Virgin Islands, and France

The Southeast Peninsula of Saint Kitts with Nevis in the Background

San Juan to Charlotte Amalie via Antilles

San Juan to Charlotte Amalie
8 Days from $3,299

Journey across the Virgin Islands from San Juan to Charlotte Amalie on this incredible 8-day cruise aboard the SeaDream I. Stroll on white-sand beaches and lose yourself watching an unforgettable blue sky as you travel.

Unspoiled beaches and pristine coves in the Caribbean

Round-trip San Juan

San Juan to San Juan
8 Days from $2,999

Board the SeaDream II and begin your unforgettable 8-day round-trip journey from San Juan through the islands of the Caribbean. Explore St. John, Jost van Dyke and others, snorkeling and biking along the way, or just relax and soak up the sun. Explore the island of Tortola on a land rover safari and master the zip line at South Friar's Bay on tour unforgettable tour.

Explore the small island of Virgin Gorda as you sail the Caribbean

Philipsburg Round Trip

Philipsburg to Philipsburg
10 Days from $7,515

Join the Sea Cloud Spirit on a spectacular 10-day round trip cruise and enjoy the opportunity to appreciate the richness of Puerto Rico and the Virgin Islands. Explore amazing places and take in the best views of during this Caribbean voyage.

Greater Antilles Travel Deals

Transatlantic Voyage from Miami to Lisbon

Miami to Lisbon
15 Days from $4,880

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 $3,230

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.

Fort Lauderdale, Florida to Bridgetown

Fort Lauderdale to Bridgetown
10 Days from $3,510

Discover the Caribbean on this 10-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.

Transatlantic Voyage from Miami to Lisbon

Miami to Lisbon
15 Days from $4,880

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

Active Tours of the Greater Antilles

Cycling through the revolutionary landscape of Cuba

Cuba Multisport

Havana to Havana
7 Days from $3,490

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.

Cuba Walking Tour

8 Days from $3,490

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 Kayaking West Tour

8 Days from $3,190

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.

Greater Antilles Travel Guide

All Greater Antilles Articles

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!

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.