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Greater Antilles Small Ship Cruises

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Greater Antilles
Picturesque Cuba
Caribbean
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Clear waters of the Caribbean sea
Antigua
Lush green forests and clear blue waters of the Caribbean
Barbados
Take a leisurely stroll through beautiful Bridgetown
Dominica
Encounter tropical wildlife while you sail on the Aranui
Grenada
Snorkel the clear, tropical waters
Lesser Antilles
Wander the white-sand beaches of St. Johns on your Virgin Islands cruise
Netherlands Antilles
Enjoy a blissful snorkeling trip.
Puerto Rico
Discover incredible history and culture in Puerto Rico
Lesser Antilles
Wander the white-sand beaches of St. Johns on your Virgin Islands cruise
St. Barth
Play on the famously beautiful beaches of St. Barth's
St. Kitts
Stroll along the beautiful beaches of the Caribbean
St. Vincent des Grenadines
Visit beautiful St. Vincent
British Virgin Islands
Relax on the beaches of the Caribbean
U.S. Virigin Islands
View gorgeous sunsets over the Virgin Islands
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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 3 Small Ship Cruises of the Greater Antilles for 2024-2025

All Greater Antilles Tours
Big brown pelicans at the Florida Keys

Insider Tip for Sailing Enthusiast

Miami to Miami
10 Days from $9,635
Experience a 10-day luxury cruise exploring Eleuthera, Exumas, and Key West. Dive into vibrant cultures and stunning landscapes aboard Sea Cloud Spirit, offering unparalleled comfort and service.
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Explore the famous rock formations of the baths

A Colorful Caribbean Time-Out

San Juan Roundtrip
8 Days from $7,500
Embark on an 8-day cruise aboard Sea Cloud Spirit sailing to explore Old San Juan's historic charm. Wander streets lined with colorful facades and salsa-filled cafes. Discover UNESCO-listed sites like La Fortaleza and Fort San Felipe del Morro, resonating with centuries of history and cultural vibrancy.
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Nassau Lighthouse

Island Odyssey: Bahamas to the Grenadines

Nassau - Bridgetown
13 Days from $23,390
Sail on this 13-day Island Odyssey: Bahamas to the Grenadines cruise from Nassau to Bridgetown aboard Scenic Eclipse. Begin the trip in Nassau then sail to Compass Cay and explore its pristine beaches, snorkel in crystal-clear waters, or spot marine life from the marina. Explore Long Island on foot or by bike and more!
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2 Best Small Cruise Ships of the Greater Antilles for 2024-2025

Ship NameMax PassengersFromSummary
Sea Cloud Spirit136$7500Sea 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 …
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Scenic Eclipse228$23390Scenic Eclipse is the World's First Discovery Yacht and the first ocean cruise ship from the Scenic fleet. Launched in August 2019, Scenic Eclipse …
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All Greater Antilles Deals

2 Greater Antilles Travel Deals for 2024-2025

Trip NameSaveFromDaysNext DepartureSummary
Island Odyssey: Bahamas to the GrenadinesCustom Label$2339013Oct 24, 2024Sail on this 13-day Island Odyssey: Bahamas to the Grenadines cruise from Nassau to Bridgetown aboard Scenic Eclipse. Begin the trip in Nassau then …
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A Colorful Caribbean Time-OutCustom Label$75008Jan 10, 2025Embark on an 8-day cruise aboard Sea Cloud Spirit sailing to explore Old San Juan's historic charm. Wander streets lined with colorful facades and …
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Top 8 Active Tours of the Greater Antilles for 2024-2025

Trip NameFromDaysNext DepartureSummary
Cuba Kayaking West Tour$33908Jun 16, 2024Experience Cuba on a unique land and kayaking program. Discover three of Cuba’s greatest resources: its people, colorful culture, and natural …
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Cuba Cycling Tour$41908Jun 10, 2024A cycling tour through western Cuba takes you off the well-traveled tourist track and onto roads where Cuba’s history may not have been made, but …
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Insider Tip for Sailing Enthusiast$963510Mar 26, 2025Experience a 10-day luxury cruise exploring Eleuthera, Exumas, and Key West. Dive into vibrant cultures and stunning landscapes aboard Sea Cloud …
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Cuba Multisport$36908Jun 10, 2024Explore the intriguing island of Cuba on this active 8-day People-to-People multisport tour. Bike, hike, and kayak wild coastal sites and tranquil …
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Cuba Walking Tour$33908Jun 10, 2024Discover natural beauty and rich Cuban heritage on this 8-day People-to-People walking tour in Cuba. Visit Cienfuegos, Trinidad, Playa Larga, …
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Classic Cuba$22455Jun 10, 2024Rolled 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 …
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A Colorful Caribbean Time-Out$75008Jan 10, 2025Embark on an 8-day cruise aboard Sea Cloud Spirit sailing to explore Old San Juan's historic charm. Wander streets lined with colorful facades and …
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Island Odyssey: Bahamas to the Grenadines$2339013Oct 24, 2024Sail on this 13-day Island Odyssey: Bahamas to the Grenadines cruise from Nassau to Bridgetown aboard Scenic Eclipse. Begin the trip in Nassau then …
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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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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.
Enjoy the beautiful blue Caribbean

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.
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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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Best Greater Antilles Small Ship Cruise Lines for 2024-2025
  • 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.


 
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    TrustScore 4.9 of 5
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    Based on 209 reviews on
    review score
    7 hours ago
    I have travelled with Adventure Life previously and certainly eager to do it again. Kassandra made excellent and honest suggestions while taking the time to understand what was important to us.
    Susan
    review score
    1 day ago
    They answered every question and concern that I had and put me at ease. Very excited for this once in a life-time trip.
    Customer Tim
    review score
    2 days ago
    I am a returning client to Adventure Life and am very pleased with their commitment to put together a great trip. Clara replied and clarified to any and all questions we had.
    Claire Palmer
    review score
    4 days ago
    Jessica was very responsive to my questions and never balked when I asked her to go back and find more options. She really worked hard to find the right cruise for us.
    Amy Siegel
    review score
    4 days ago
    Friendly, accommodating, knowledgeable, timely. They have made us feel very comfortable for our trip!
    Gregg Chamberlain

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