Top 10 Lesser Antilles Caribbean Small Ship Cruises for 2022-2023

Philipsburg Roundtrip
8 Days from $4,755

Discover deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the islands' sugar cane fields and spice plantations. The scent of cloves, cinnamon, and nutmeg hang in the air wherever you go.

Grenadine Islands

Bridgetown to Bridgetown
8 Days from $2,420

On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of nature on this Caribbean adventure.

Dock going out into the crystal blue ocean

Classic Yachtsman Caribbean

Antigua to Barbados
8 Days from $2,420

Royal Clipper offers the ultimate sea-going experience as you travel to the beautiful beaches and landscapes of the Caribbean. This 8-day sailing journey is unforgettable, with destinations including Barbados, St. Lucia, Dominica, Antigua, Martinique, and more!

Sailing the Caribbean

8 Days from $10,880

Experience the Caribbean in the most authentic way under the 30 white sails of Sea Cloud on this 8-day round trip cruise of Barbados. As you delight in the comfort of this sailing schooner, there will be opportunities to snorkel the vibrant reefs of these turquoise waters, and relax on the beaches of Dominica, the Grenadines, and St. Lucia.

Stroll along the white sandy beaches of St. Barth's

Relaxed Festive Days Under Palms

Round-trip Philipsburg
17 Days from $10,185

Cruising the perfect dream of tall ships: Encounter volcanic islands, laid-back sailors' haunts, and colorful underwater worlds. Join the luxurious Sea Cloud on this fantastic 15-day small ship cruise.

Play on the famously beautiful beaches of St. Barth's

Enjoy Caribbean Rhythms at the Turn of the Year

Caribbean: Round-trip Philipsb
16 Days from $8,195

Explore the best of the Caribbean on this cruise aboard the Sea Cloud. From the Dutch Colonial port town of Philipsburg, sail to the British Virgin Islands, Grenada, and St. Vincent and the Grenadines. From there cruise to St. Lucia, Antigua, and Barbuda. Relax in Gustavia on St. Barthelemy, then stop in Anguilla before returning to Philipsburg.

Stroll along the beautiful beaches of the Caribbean

Front Row Seat at the Famous Bucket Regatta

Round-trip Philipsburg
11 Days from $7,495

Delight yourself with deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the island’s sugar cane fields and spice plantations. The scent of cloves, cinnamon, and nutmeg hang in the air wherever you go.

Windjammer Rendezvous in the Lesser Antilles

Philipsburg Roundtrip
12 Days from $6,785

On this 12-day voyage aboard Sea Cloud, windjammers can enjoy the Caribbean's lush green landscapes, stunning beaches, a relaxed sailor lifestyle, and a vibrant undersea world along the Lesser Antilles.

Panama to Antigua

15 Days from $4,300

Starting in Balboa, Panama, sail through warm Caribbean waters as you make your way to the Antigua aboard the Royal Clipper. Over the course of 15 days visit Grenada, Bonaire, Curacao, Aruba, and Colombia before arriving in Panama.

Windward Islands

Bridgetown to Bridgetown
8 Days from $2,420

Board the luxurious Royal Clipper sailing ship for this 8-day roundtrip cruise of the Caribbean, departing from Bridgetown, Barbados to St. Lucia, Dominica, Antigua, St. Kitts, Martinique, and more! Snorkel in turquoise reefs, explore tropical rainforests, relax on the sun-kissed beaches, and delight in exotic markets and charming seaside cafes.

All Lesser Antilles Luxury Small Ship Cruises

9 Best Lesser Antilles Luxury Caribbean Small Ship Cruises for 2022-2023

Trip Name	From	Days	Next Departure	Summary
Relaxed Festive Days Under Palms	$10185	17	Dec 20, 2022	Cruising the perfect dream of tall ships: Encounter volcanic islands, laid-back sailors' haunts, and colorful underwater worlds. Join the luxurious … 0
Christmas and New Year in the Caribbean	$6180	13	Dec 23, 2022	Spend an unforgettable festive season celebrating Christmas and New Year's in the Caribbean aboard Le Dumont-d'Urville. Cruise from Fort-de-France to … 0
Pearls of the Caribbean	$3840	9	Nov 25, 2022	Join Le Dumont-d'Urville on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea … 0
Pure Sailing- Crossing the Atlantic	$14430	18	Nov 25, 2022	Sail across the Atlantic Ocean on this exclusive 18-day, once-in-a-lifetime offshore adventure on the Sea Cloud schooner. Enjoy an authentic sailing … 0
Dream of A Lifetime: Transatlantic Crossing	$14245	18	Nov 27, 2023	Be a part of a unique 18-day Transatlantic sailing experience aboard the luxurious Sea Cloud. Cruise across the magnificent Atlantic Ocean on your … 0
In the heart of the West Indies : Bridgetown - Vieux Fort	$3840	9	Mar 5, 2023	The Dumont-d'Urville offers a 9-day Caribbean trip that takes you to the most beautiful islands in the region. Begin your journey from Bridgetown to … 0
Transatlantic:Malaga to St.Maarten	$3940	25	Nov 2, 2022	This once-in-a-lifetime sailing expedition starts at the tropical paradise island of St. Maarten and voyages across the Atlantic Ocean all the way to … 0
Santo Domingo and Caribbean treasures	$5760	13	Jan 4, 2023	From Santo Domingo to Fort-de-France, succumb to the charms of the Caribbean aboard a new 13-day cruise. Swimming and spectacular discoveries await … 0
Pure Sailing- Crossing the Atlantic	$12540	17	Nov 29, 2022	Sail around the Atlantic ocean as Sea Cloud II sail from the island on the Southwest coast of Praia to Gustavia enjoying the beautiful beaches and … 0

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Lesser Antilles Travel Guide

Best Time to Visit the Lesser Antilles?

Get information about the dry versus wet season weather averages in Trinidad, Tobago, and Barbados.

Caribbean Cruise: When to Go?

Discover the best time of year to sail the Caribbean on a small ship or sailboat. Find the best month for your Caribbean cruise, whether you want an active vacation spent kayaking, snorkeling and fishing, or a restful time just lounging by the clear turquoise water.

Blowing where the wind takes us on the Liberty Clipper

Caribbean Cruises

Small ships provide a fun and unique way to explore the islands of the Caribbean. Water activities can be conveniently planned from the vessel, and time spent on board always provides beautiful scenery as well as good company.

Best Lesser Antilles Small Ship Cruise Lines for 2022-2023

Ponant - serves as a global ambassador for the "French Touch." It makes every effort to keep its particular cruising philosophy, with a French crew, discreet service, sophisticated cuisine, and established partners. Your dream of the Lesser Antilles, Caribbean cruise onboard the cozily intimate ship Le Champlain is thus made possible through the combination of an authentically genuine voyage experience together with discreet luxury.
Silversea Cruises - Known for their exquisite onboard service and innovative, enticing itineraries, Silversea cruises let you discover some of the world's most captivating destinations. A Caribbean island cruise transports you to mild breezes and swaying palm trees. Silver Wind enables you to escape to the yachting havens of the Lesser Antilles, which are inaccessible to big ships.
Lindblad Expeditions - return to the romantic era of tall ships on a voyage among the idyllic islands of the Caribbean—a place perfectly suited to the aesthetic beauty of sailing aboard an authentic square-rigger. The iconic ship Sea Cloud serves as a home base for exploring the Caribbean's hidden gems and the Lesser Antilles.
Star Clippers Americas - a modern cruise line that re-creates the famous clippers that sailed the oceans in the 19th century and offers a chance to cruise onboard the Tall Ship Royal Clipper in the Lesser Antilles in the Caribbean Sea.