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

All Greater Antilles Tours
Nassau Lighthouse

Caribbean Escapade

San Juan to Miami
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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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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The crystal blue water of Jost van Dyke

Jamaica to Antigua

Port Antonio to St. John's
12 Days from $2,720
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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Deans Blue Hole

West Caribbean Cruise

Belize - Fort Lauderdale
11 Days from $3,580
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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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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Explore the famous rock formations of the baths

Quintessential Caribbean

San Juan to St. Thomas
8 Days from $7,990
Embark on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore the vibrant culture of San Juan, the charm of Saint John, the tranquil beaches of Nevis, the picturesque village of Deshaies, the historic allure of Falmouth Harbour, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays. Enjoy unique experiences and stunning landscapes throughout your cruise.
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Explore beautiful Jost van Dyke

Caribbean Yachting Hideaways

St Thomas - St John's
8 Days from $7,190
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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St Barts harbor view

Caribbean Yachting Discovery

St. John's to San Juan
8 Days from $10,490
Experience a luxurious 8-day Caribbean yacht cruise from St. John’s to San Juan aboard an Emerald Cruises luxury yacht. Discover stunning beaches, vibrant towns, and rich history in Barbuda, Iles des Saintes, Deshaies, Gustavia, Jost Van Dyke, and Norman Island.
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A dish created by Chef Ben Robinson

Caribbean Yachting Discovery with Chef Ben Robinson

St. John's to San Juan
8 Days from $6,966
Embark on an 8-day Caribbean cruise with Chef Ben Robinson aboard the Emerald Azzurra. Enjoy a welcome reception, cooking demo, and special dinners. Explore Barbuda’s pink-sand beaches, Iles des Saintes, Deshaies, Gustavia, and Norman Island.
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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$35805-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$41908Nov 24, 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$31258Nov 24, 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$36908Nov 24, 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$35908Nov 24, 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.
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.


 
    TrustScore 4.8 | 383 reviews
    TrustScore 4.8 of 5
    total score
    Based on 383 reviews on
    review score
    6 hours ago
    Kassandra is knowledgeable, efficient and very pleasant to work with.
    Fred Weeman
    review score
    2 days ago
    The booking was processed efficiently and quickly. We got what we wanted.
    Doug Laporte
    review score
    2 days ago
    Great company. Good communications. Great accommodations, excursions, transport. Guide Elvira was spectacular along with transport, driver, Cesar and activities
    Kathy S
    review score
    3 days ago
    Very responsive to questions. Helpful with all arrangements
    Roz
    review score
    4 days ago
    The ship company they sent us on was perfect in every detail
    lisa wegener

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