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Greater Antilles Small Ship Cruises

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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
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Top 9 Small Ship Cruises of the Greater Antilles for 2025-2026

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All Greater Antilles Luxury Tours

Best 3 Luxury Small Ship Cruises of the Greater Antilles for 2025-2026

Trip NameSaveFromDaysNext DepartureSummary
Caribbean Yachting HideawaysCustom Label$71908Dec 21, 2024Embark on an 8-day Caribbean adventure aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches, Vieques’ lovely waterfront, Cruz …
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Caribbean Yachting DiscoveryCustom Label$79908Dec 28, 2024Set sail on an 8-day cruise aboard the Emerald Azzurra, uncovering pristine beaches and vibrant coral reefs while island-hopping through a tapestry …
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Caribbean Yachting Discovery with Chef Ben RobinsonCustom Label$69668Jan 25, 2025Embark on an 8-day Caribbean cruise with Chef Ben Robinson aboard the Emerald Azzurra. Enjoy a welcome reception, cooking demo, and special dinners. …
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5 Best Small Cruise Ships of the Greater Antilles for 2025-2026

Ship NameMax PassengersFromSummary
Emerald Azzurra100$6966As Emerald's first-ever ocean superyacht, the luxurious Emerald Azzurra is designed to take up to 100 passengers sailing along the Adriatic Coast, …
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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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Star Clipper170$2720Star Clipper is a 170-passenger vessel designed to provide a unique traveling experience unlike any other cruise vacation. Step aboard and discover a …
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Emerald Sakara100$7590Emerald Cruises brings our award-winning reputation and service to the world?s oceans and coastlines as we introduce Luxury yacht cruising on our …
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SH Vega152$43805-star elegant Scandi-design boutique ship offers you an intimate setting from which you will be fully immersed in all the sights and scenery of your …
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Top 5 Active Tours of the Greater Antilles for 2025-2026

Trip NameFromDaysNext DepartureSummary
Cuba Kayaking West Tour$35908Jan 1, 2025Experience 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$41908Dec 19, 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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Dominican Republic: Culture and Cocktails$31258Dec 19, 2024This 8-day journey will give you a genuine taste of the Dominican Republic. From UNESCO World Heritage Sites to street art and local delicacies, …
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Cuba Multisport$36908Dec 19, 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$35908Dec 19, 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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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...
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.
Best Greater Antilles Small Ship Cruise Lines for 2025-2026
  • 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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