Have questions? We're here.

Caribbean Small Ship Cruises

Travel made your way
Grenada
Hugh Whyte
Georgian Architecture, St. George's | Grenada
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
A Caribbean cruise on a small ship or sailboat (Windjammer) is the best way to explore the turquoise waters, beaches, rich marine life and cultures of the Caribbean. The vessel you choose for your Caribbean cruise has a dramatic impact on the experience. On a small sailboat or small luxury ship with only 24-250 passengers aboard, you can access small coves, reefs and ports that are impossible on a huge cruise ship carrying hundreds or even thousands of passengers. Enjoy the serenity of sailing on a small sailboat like the Mandalay, Panorama, or the Liberty Clipper. Up the ante on a luxury small ship like the Variety Voyager, or new Le Champlain and Le Dumont-d'Urville by Ponant. Escape the average Caribbean cruise by having one of our small ship Caribbean cruise experts help design you the perfect trip.
All Caribbean Cruises

10 Best Caribbean Small Ship Cruises for 2023-2024

All Caribbean Cruises

Top 3 Luxury Caribbean Small Ship Cruises for 2023-2024

Trip NameFromDaysNext DepartureSummary
Hidden Charms of the Caribbean$45108Nov 25, 2023Embark on an 8-day Caribbean adventure, sailing from San Juan to St John's aboard the luxurious Emerald Sakara. Discover the hidden gems of the …
0
Pearls of the Caribbean$42909Nov 5, 2023Join Le Bellot on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea visiting Port …
0
Dream of A Lifetime: Transatlantic Crossing$1424518Nov 27, 2023Be a part of a unique 18-day Transatlantic sailing experience aboard the luxurious Sea Cloud. Cruise across the magnificent Atlantic Ocean on your …
0

Caribbean Cruise Destinations

8 Best Small Caribbean Cruise Ships & Sailboats for 2023-2024

Ship NameMax PassengersFromSummary
Royal Clipper227$1660The Royal Clipper is the largest full-rigged sailing ship in the world, carrying just 227 privileged guests aboard. She offers the ultimate tall ship …
0
Sea Cloud II94$4655The Sea Cloud II is a legendary windjammer comparable to her sister ship, the Sea Cloud. Featuring her own unique character, the Sea Cloud II …
0
Liberty Clipper24$1499The Liberty Clipper is a 125-foot beautifully renovated gaff-rigged schooner, a replica of the renowned Baltimore Clippers, made famous over a …
0
Le Dumont-d'Urville184$4050Discover a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with …
0
Sea Cloud64$4755With occupancy for just 64 guests, the Sea Cloud is a modern and elegant windjammer outfitted with modern amenities and uniquely decorated cabins. …
0
Sea Cloud Spirit136$4945Sea 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
Variety Voyager72$3390The sleek & modern Variety Voyager is a state of the art mega-yacht which accommodates just 72 passengers in 36 cabins. Enjoy unobstructed views of …
0
All Caribbean Videos

Caribbean Sailing Cruise Video

All Caribbean Articles

Caribbean Small Ship Cruising Guide & Travel Tips

Highlights of the Caribbean

The Lesser Antilles 
 are home to some of the most popular destinations in  the Caribbean, like the Virgin Islands, St. Lucia & St. Martin, where delightful cafes, tranquil towns, and serene beaches highlight the sea side scenery.

The Grenadines: 
Sail to Grenada, Bequia, Union Island, Mayreau, Tobago Cays, Carriacou, Sandy Island, Canouan and Happy Island; try some of the famous local Caribbean rum; relax on the beach; or participate in various land excursions.

The Bahamas: As you cruise through the Bahamas on a small sailboat, get into the groove of the laid back lifestyle of the islands, the culinary delights of the local cuisine, and perhaps even have a chance to try hoisting the sails or taking over the helm of your sailboat.

The Virgin Islands: Offer you some of the best snorkeling opportunities in the whole Caribbean, featuring crystal clear waters and diverse marine life, in addition to stops in charming port towns along the way, where you can get a taste of the local island culture.

The Panama Canal: In the far south of the Caribbean, see the breathtaking marvel that is the Panama Canal, when the greatest minds and thousands of dedicated workers labored internationally to connect the Atlantic & Pacific trade routes.
 
What to Expect on a Luxury Caribbean Cruise
When you book a luxury Caribbean cruise aboard one of our hand-selected small ships, you are signing up for an unforgettable combination of comfort and service. 

We feature only small ships, yachts, and windjammers for our luxury Caribbean cruises, because we believe that this should be an intimate experience that you share with your loved ones, and that's exactly the ambiance the small ships offer. 

While each ship has a unique design, we guarantee elegance and style, in addition to comfortable and spacious suites - often with their own private balconies - and the best onboard amenities of any small Caribbean ships.

Luxury cruises offer all kinds of included activities to fill your days, but there are also add-on packages that can bring even more adventure and exploration to your itinerary. Plus there's plenty of free time built in to these cruises at each port so that you can simply relax on the beach and meander around the small towns if you prefer.
 

Video: Sailing the Caribbean on a Small Ship Cruise

All Caribbean Travel Stories

Caribbean Adventure Cruise Stories

Top Caribbean Travel Destinations

Caribbean Trips by Departure Date

Top Experiences in Caribbean

Caribbean Trips by Duration

Caribbean Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By