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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

All Greater Antilles Small Ship Cruises
All Greater Antilles Luxury Tours

Best 5 Luxury Small Ship Cruises of the Greater Antilles for 2025-2026

Trip Name From Days Summary
Caribbean Yachting Hideaways $8,390 8 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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Caribbean Yachting Discovery $7,990 8 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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Pristine Islands of the Bahamas & the Panama Canal $24,990 11 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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Sounds of Discovery: New York to the Bahamas $24,990 13 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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Island Odyssey: Bahamas to the Grenadine $19,990 11 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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6 Best Small Cruise Ships of the Greater Antilles for 2025-2026

Ship Name Max Passengers From Summary
Star Clipper 170 $1,740 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 100 $7,990 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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Silver Spirit 608 $4,800 Silver Spirit is a luxury cruise ship in the Silversea Classic fleet, offering an intimate, all-suite experience with exceptional dining and personalized service. It sails to Northern Europe & the British Isles, the Mediterranean, Transoceanic routes, and the Caribbean & Central America.
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Top 1 Active Tours of the Greater Antilles for 2025-2026

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.
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

  • 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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