Top 10 Small Ship Cruises of the Greater Antilles for 2021-2022

Relax in the sunny squares of historic Savannah

Board M/V Victory I 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.

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East Coast USA Adventure

Boston to Nassau
9 Days from $7,895

Tracing down the historic eastern seaboard of the USA and into the shimmering Caribbean, this 9-day voyage is perfect for those who enjoy the stunning scenery, alluring architecture, rich history, and vibrant culture of the United States' east coast.

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Havana to Cienfuegos

Havana to Cienfuegos
11 Days from $6,910

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.

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Havana to Santo Domingo

Havana to Santo Domingo
13 Days from $6,985

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.

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San Juan to San Juan

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

What better way to see the brilliant turquoise waters of the Caribbean than on this exclusive 8-day small ship cruise aboard SeaDream II. The cruise takes in 9 diverse islands of the Caribbean on a roundtrip voyage from San Juan to Punta Cana, Isla Saona, Caja de Muertos, Esperanza, and more. Reserve a yachting land adventure or take advantage of the watersports marina.

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Colorful flowers and bright blue sea in the Caribbean

San Juan Round-trip

via Spanish Town
6 Days from $2,499

Fall in love with the Caribbean on this exclusive 6-day roundtrip cruise from Puerto Rico! Discover a world of grottos amidst giant boulders on the island of Virgin Gorda, capture the French ambiance of St. Barts by day and night, or explore the unspoiled national park of St. John. Celebrate the yachting lifestyle aboard SeaDream II.

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Relax on the sunny beaches of the Bahamas

Palm Beach to Palm Beach

Palm Beach to Palm Beach
8 Days from $3,599

Fall in love with the Bahamas on this exclusive 8-day Caribbean roundtrip cruise from Palm Beach. Discover the pristine charm of Rose Island, explore the azure waters of Norman's Cay, and capture the exotic cliffs and caves of Long Island. Celebrate the yachting lifestyle aboard SeaDream II.

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Central America & Cuba: Colon - Havana

Colon to Havana
15 Days from $9,005

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

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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 M/V Victory I.

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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.

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All Greater Antilles Luxury Tours

Best Luxury Small Ship Cruises of the Greater Antilles

All Greater Antilles Luxury Tours

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.

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All Greater Antilles Small Ship Cruises

Best Small Ship Cruises of the Greater Antilles

All Greater Antilles Small Ship Cruises

Sea Cloud II

The Sea Cloud II is a legendary windjammer comparable to her sister ship, the Sea Cloud. Featuring her own unique character, the Sea Cloud II combines the high standards expected of a 5-star cruise ship with the unique atmosphere of a romantic tall ship.

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Scenic Eclipse

Scenic Eclipse is the World’s First Discovery Yacht and the first ocean cruise ship from the Scenic fleet. Launched in August 2019, Scenic Eclipse sets a new standard in luxury ocean cruising. With elegant lines, perfectly-proportioned suites, and expansive wellness zones, every element of Scenic Eclipse has been considered with your enjoyment and pleasure in mind, creating a special environment that facilitates global adventure in truly 6-star luxury.

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Le Dumont-d'Urville

Experience a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with environmentally-friendly equipment. Le Dumont-d'Urville features elegantly designed cabins, spacious suites with windows, and lounge areas opening on to the outside, offering a unique cruising experience.

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M/V Victory I

Skillfully designed to foster a convivial atmosphere, the M/V Victory I invite you to relax and unwind as you discover the world’s most remarkable coastal regions. Soak up a private ocean view in your choice of stateroom. Enjoy quiet time in a cozy corner. Stretch your legs on the promenade. Or gather with friends as you watch the world go by.

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Le Champlain

Experience a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with environmentally-friendly equipment. Le Champlain features elegantly designed cabins, spacious suites with windows, and lounge areas opening on to the outside, offering a unique cruising experience.

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Silver Whisper

Experience the Silver Whisper relaxing, sophisticated and genuinely elegant atmosphere. This multi-million dollar refit makes her one of the most technically up to the minute ships at sea. Admire the stunning beauty of Europe & the Caribbean aboard this 382 passenger ship.

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Liberty Clipper

The Liberty Clipper is a 125-foot beautifully renovated gaff-rigged schooner, a replica of the renowned Baltimore Clippers, made famous over a century ago for their speedy and safe rounding of Cape Horn on expeditions to the California Gold Rush. Her authentic design is exceeded only by a state-of-the-art galley, modern accommodations for up to 24 guests, and a beautifully adorned grand salon.

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SeaDream I

The SeaDream I is a chic and stylish yacht designed to accommodate 112 passengers in an intimate and comfortable atmosphere. Cruise along the Caribbean's warm waters or explore the culture of the Mediterranean on a unique luxury cruise.

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Active Tours of the Greater Antilles

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.

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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.

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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.

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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!

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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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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.