Have questions? We're here.

Greater Antilles Small Ship Cruises

Travel made your way ™
Greater Antilles
Picturesque Cuba
Caribbean
iStock
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
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Talk with an expert
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 9 Small Ship Cruises of the Greater Antilles for 2024-2025

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.
0
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.
0
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.
0
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.
0
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!
0
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.
0
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.
0
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.
0
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.
0
All Greater Antilles Luxury Tours

Best 2 Luxury Small Ship Cruises of the Greater Antilles for 2024-2025

Trip NameSaveFromDaysNext DepartureSummary
Caribbean Yachting Hideaways$71908Dec 7, 2024Embark on an 8-day Caribbean adventure aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches, Vieques’ lovely waterfront, Cruz …
0
Caribbean Yachting Discovery$104908Dec 28, 2024Experience a luxurious 8-day Caribbean yacht cruise from St. John’s to San Juan aboard an Emerald Cruises luxury yacht. Discover stunning beaches, …
0

5 Best Small Cruise Ships of the Greater Antilles for 2024-2025

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, …
0
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 …
0
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 …
0
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 …
0
Scenic Eclipse228$23390Scenic Eclipse is the World's First Discovery Yacht and the first ocean cruise ship from the Scenic fleet. Launched in August 2019, Scenic Eclipse …
0

Top 2 Active Tours of the Greater Antilles for 2024-2025

Trip NameFromDaysNext DepartureSummary
Cuba Kayaking West Tour$28508Oct 6, 2024Experience Cuba on a unique land and kayaking program. Discover three of Cuba’s greatest resources: its people, colorful culture, and natural …
0
Dominican Republic: Culture and Cocktails$28508Sep 13, 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, …
0
All Caribbean Videos

Greater Antilles Videos

All Caribbean Articles

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!
0
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.
0
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.
0
Best Greater Antilles Small Ship Cruise Lines for 2024-2025
  • 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 4.9 | 313 reviews
    TrustScore 4.9 of 5
    total score
    Based on 313 reviews on
    review score
    22 minutes ago
    Excellent, friendly, and knowledgeable service and assistance.
    Vaughna Cochenour
    review score
    5 hours ago
    Was very easy to come up with an itinerary that included everything I wanted in a trip to Nepal with good communication, prompt service and really felt my needs were considered.
    Robert
    review score
    7 hours ago
    Jess was terrific and patiently guided us to make what we feel will be a wonderful family adventure.
    David Herr
    review score
    14 hours ago
    My family and I had been dreaming of going to Africa for two decades and our dream finally came true! I cannot begin to explain what an incredible experience we had working with Adventure Life, and specifically with Jason Maynard and his assistant Kriska Buison. From the deep knowledge of just about every activity, location and venue, to the patience and perseverance he had in working with us until we crafted the absolute perfect trip. We made a video that captures our experience, two of the most amazing weeks of our life... enjoy! To view it, you can go to YouTube and find my profile xdeanda and find my video "East Africa, summer 2024"
    Xavier
    review score
    1 day ago
    From the initial booking all the way through the trip, this was by far our favorite trip. Small boat travel is the only way to see a location. The excursions were so much more than I could explain. The locations were remote and awesome.
    Lori I

    Caribbean Travel Guide

    Favorite Caribbean All Trips

    Top Greater Antilles Travel Destinations

    Greater Antilles Trips by Departure Date

    Top Experiences in Greater Antilles

    Greater Antilles Trips by Activity

    More Reasons

    Why Travel With Adventure Life

    All News

    Recognized By

    Plan My Trip
    We love travel, talk with an expert 1.800.344.6118