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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 10 Small Ship Cruises of the Greater Antilles for 2025-2026

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Nassau Lighthouse

Caribbean Escapade

8 Days from $7,590
Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore Grand Turk's pristine beaches and historic landmarks, discover Long Island's tranquil Gordon's Beach, and dive into San Salvador's vibrant coral reefs and historic sites. Enjoy the white sands of Emerald Bay in The Bahamas and visit Nassau's vibrant cityscape and historic sites.
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Kayaking in Cuba

Cuba Kayaking West Tour

8 Days from $3,390
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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Bicycle on Cuban street

Cuba Cycling Tour

8 Days from $4,390
A 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 where it was lived every day. It reveals to you to Cuba’s true resource, its true legend: its people.
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The crystal blue water of Jost van Dyke

Jamaica to Antigua

12 Days from $3,090
Explore a paradise of vibrant coral reefs, powder-soft sand, and warm island hospitality on this 12-day cruise from Jamaica to Antigua aboard Star Clipper. Experience crystal-clear water, bright skies, and gentle breezes. Relish in the beauty of untouched beaches and become enchanted by seductive scents and rhythms.
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Cayo Arena Island

Dominican Republic: Culture and Cocktails

8 Days from $3,125
This 8-day journey will give you a genuine taste of the Dominican Republic. From UNESCO World Heritage Sites to street art and local delicacies, immerse yourself in the diverse landscapes and cultures of this Caribbean gem. With optional beach extensions, savor every moment of your unforgettable journey.
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Explore the famous rock formations of the baths

A Colorful Caribbean Time-Out

8 Days from $5,245
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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Cycling through the revolutionary landscape of Cuba

Cuba Multisport

8 Days from $3,890
Explore the intriguing island of Cuba on this active 8-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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Deans Blue Hole

West Caribbean Cruise

11 Days from $4,380
Embark on an 11-day SH Vega cruise through the Western Caribbean. Explore Mayan ruins in Belize, relax on Grand Cayman's beaches, snorkel Montego Bay’s reefs, and visit Jamaica’s mountains. Enjoy birdwatching at Great Inagua, swim with sharks in the Exumas, and marvel at Nassau’s beauty.
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Havana Musicians

Classic Cuba

5 Days from $2,245
Rolled 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 classic Cuba tour. Find yourself immersed in legendary Cuban culture as you explore legendary Havana, the tobacco mecca Vuelta Abajo, and breathtaking Valle de Viñales.
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Explore beautiful Jost van Dyke

Caribbean Yachting Hideaways

8 Days from $7,740
Embark on an 8-day Caribbean adventure aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches, Vieques’ lovely waterfront, Cruz Bay’s scenic hikes, and Virgin Gorda’s famous Baths. Discover Philipsburg’s vibrant culture, Gustavia’s idyllic beaches, and Montserrat’s volcanic history.
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All Greater Antilles Luxury Tours

Best 1 Luxury Small Ship Cruises of the Greater Antilles for 2025-2026

Trip Name From Days Next Departure Summary
Caribbean Yachting Discovery $7,990 8 Dec 13, 2025 Set sail on an 8-day cruise aboard the Emerald Azzurra, uncovering pristine beaches and vibrant coral reefs while island-hopping through a tapestry of diverse cultures. Let the genuine warmth of the locals add a personal touch to your luxurious yacht adventure.
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5 Best Small Cruise Ships of the Greater Antilles for 2025-2026

Trip Name From Days Next Departure Summary
Star Clipper $1,930 May 10, 2025 Star Clipper is a 170-passenger vessel designed to provide a unique traveling experience unlike any other cruise vacation. Step aboard and discover a new age of sailing, where the traditions of the past are happily married to the comforts and amenities of the present day.
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Emerald Azzurra $7,190 Apr 26, 2025 As Emerald's first-ever ocean superyacht, the luxurious Emerald Azzurra is designed to take up to 100 passengers sailing along the Adriatic Coast, Red Sea, and the Eastern and Western Mediterranean.
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SH Vega $4,380 May 21, 2025 5-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 voyage.
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Emerald Sakara $7,590 Jun 07, 2025 Emerald Cruises brings our award-winning reputation and service to the world?s oceans and coastlines as we introduce Luxury yacht cruising on our brand new, innovative superyachts, custom-designed to allow unique access to the fascinating ports and harbors only small yachts can reach.
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Sea Cloud Spirit $4,850 Jul 24, 2025 Sea 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 with a high comfort level and enjoying the best panorama views.
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All Greater Antilles Deals

1 Greater Antilles Travel Deals for 2025-2026

Trip Name From Days Next Departure Summary
Cuba Walking Tour $3,590 8 Apr 21, 2025 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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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 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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