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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 Small Ship Cruises

Top 10 Small Ship Cruises of the Greater Antilles for 2026-2027

All Greater Antilles Small Ship Cruises
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.
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Deans Blue Hole

West Caribbean Cruise

10 Days from $5,175
Embark on an 10-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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Pig Beach in Exuma, Bahamas where wild pigs swim in the clear turquoise waters

Island Odyssey: Bahamas to the Grenadine

11 Days from $19,990
Set sail on an 11-day Caribbean cruise from Nassau to Bridgetown on the Scenic Eclipse, visiting remote gems like Staniel Cay, Turks and Caicos, and St. Barts. Enjoy ultra-luxury amenities and guided excursions for a refined and relaxing experience.
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Explore beautiful Jost van Dyke

Caribbean Yachting Hideaways

8 Days from $8,390
Set sail on an 8-day cruise from San Juan to St. John aboard the Emerald Azzurra, exploring stunning beaches and vibrant island towns. Visit highlights like Culebra, Vieques, and Saint Barthelemy while enjoying premium comfort and seamless access to diverse ports.
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Relax on the sunny beaches of the Bahamas

Sounds of Discovery: New York to the Bahamas

13 Days from $24,990
Experience a 13-day cruise from New York City to Nassau aboard the Scenic Eclipse, featuring stops in Bermuda, Turks and Caicos, San Salvador, Bimini, and Miami. This journey blends culture, history, and relaxation.
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Explore the famous rock formations of the baths

Splendours of the Caribbean

7 Days from $9,190
Sail through the Caribbean on a 7-day cruise aboard Emerald Sakara, from San Juan to Saint Thomas. Visit Saint John, Nevis, Antigua, Saint Barthelemy, and Virgin Gorda. Discover colonial towns, quiet beaches, and historic sites.
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Islands of the Caribbean

Quintessential Caribbean

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 Harbor, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays.
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Caribbean landscapes and harbors

Discover the Yachting Islands of the Caribbean

15 Days from $21,980
Embark on a 15-day cruise with Emerald Azzurra, exploring the Caribbean from St. John’s, Antigua, with stops at stunning destinations like Barbuda, Guadeloupe, and the British Virgin Islands. Enjoy snorkeling in Culebra and the relaxed vibe of Esperanza on Vieques, all amidst beautiful beaches and vibrant island culture.
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Paradise Tropical Island - Bocas del Toro archipelago - Island Colon

Pristine Islands of the Bahamas & the Panama Canal

11 Days from $24,990
Join an 11-day cruise from Nassau to Panama City on the Scenic Eclipse, exploring the Bahamas' clear waters and vibrant island cultures. Experience highlights like Pig Beach and the Panama Canal, blending leisure with cultural discovery.
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St Barts harbor view

Caribbean Yachting Discovery

8 Days from $8,390
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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4 Best Small Cruise Ships of the Greater Antilles for 2026-2027

Ship Name Max Passengers From Summary
Emerald Azzurra 100 $8,390 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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Emerald Sakara 100 $7,590 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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SH Vega 152 $5,175 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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Scenic Eclipse 228 $19,990 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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Top 1 Active Tours of the Greater Antilles for 2026-2027

Trip Name From Days Summary
Dominican Republic: Culture and Cocktails $3,793 8 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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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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Best Greater Antilles Small Ship Cruise Lines for 2026-2027

  • Emerald Cruises - founded in 2013, offers award-winning river and yacht cruises with all-inclusive dining, handpicked excursions, and seamless transfers for a worry-free journey. Emerald Sakara cruises the Greater Antilles' gorgeous white-sand beaches and crystalline waters fringed by palm trees.
  • Star Clippers Americas - inspired by the romance of 19th-century sailing ships, offers tall ship voyages that blend nautical heritage with modern comfort. The Star Clipper, carrying 170 guests across 85 cabins, features expansive teak decks, two swimming pools, elegant dining, and classic nautical décor, creating a private-yacht-style cruise filled with adventure and timeless charm.
  • Scenic Cruises - redefines luxury travel with all-inclusive river cruises, ultra-luxury yacht voyages, and award-winning service designed for total comfort and cultural immersion. Scenic Eclipse, the world’s first Discovery Yacht, carries up to 228 guests (200 in polar regions) and combines 6-star luxury with cutting-edge technology, offering unforgettable journeys across the world’s most inspiring destinations.



 

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