Take a small ship cruise to the beautiful archipelago of the Lesser Antilles that make up a volcanic island arc between the Greater Antilles and South America. Visit the islands of Grenada, the Grenadines, the Virgin Islands, St. Lucia, San Maarten, and beyond. Snorkel, swim, and sail around numerous Caribbean Islands while relaxing on pristine sunny beaches as you meet friendly locals. Consider traveling on a small ship cruise in order to be able to access smaller, beaches reefs and coves. Contact Adventure Life's Caribbean cruise experts for help designing the perfect cruise to the Lesser Antilles.

Top Lesser Antilles Caribbean Cruises for 2020

Name: Lesser Antilles Tours & Travel
Brand: Adventure Life
Rating: 4.9 (334 reviews)

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

Caribbean: Round-trip Philipsburg

Philipsburg to Philipsburg
15 Days from $9,265

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.

Beach, harbor and village of Terre-de-Haut

Caribbean: Bridgetown to Bridgetown

Bridgetown to Bridgetown
12 Days from $7,945

Join the Sea Cloud on this 12-day sailing adventure from Bridgetown, Barbados. Clear your mind in this paradisaical destination that mixes adventure and relaxation perfectly.

Bridgetown Round-trip

Bridgetown to Bridgetown
10 Days from $4,400

Discover the Caribbean on this 10-day sailing adventure. Visit the colorful small towns and exceptional beaches this archipelago is famous for as you sit back and relax aboard the Silver Whisper while sailing in one of the most exclusive regions in the world.

Leeward Islands

8 Days from $2,240

The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Nevis, Dominica, Iles des Saintes, Guadeloupe, Antigua, and St. Barts. As the wind blows your ship across turquoise waters through thousands of cays, snorkel in the clear water, relax on sunny beaches or hike to the tropical mountaintops.

British Virgin Islands + Leeward Islands

Philipsburg to Tortola
12 Days from $3,875

Set a course for the Caribbean and discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting to be conquered by adventurers like you.

Caribbean: Round-trip Bridgetown via Bequia

Bridgetown to Bridgetown
8 Days from $5,595

Discover the Caribbean on this 8-day sailing adventure. Delight yourself with the perfect Barbados weather, visit Man-o-War Bay, St. George, Chatham Bay, Port Elizabeth and more on this once-in-a-lifetime cruise aboard the Sea Cloud.

Enjoy the natural beauty of the Caribbean

Leeward Islands + British Virgin Islands

Tortola to St. Kitts
12 Days from $3,875

Set a course for the Leeward Islands and discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting to be conquered by adventurers like you.

Stroll along the beautiful beaches of the Caribbean

Caribbean: Round-trip Philipsburg

Philipsburg to Philipsburg
8 Days from $4,555

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.

A snorkeler walking along a white sandy beach.

Round-trip Charlotte Amalie via St. John

Charlotte Amalie to Charlotte Amalie
8 Days from $3,499

Starting and ending in Charlotte Amalie, St. Thomas, explore undiscovered gems of the Caribbean as you sail this incredible region. Enjoy adventure options and incredible views of the Caribbean's paradisaical islands.

Pearls of the Caribbean

Fort de France to Fort de France
8 Days from $3,420

Join the Le Champlain on its 8-day sailing expedition to explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, St. George's, Saint Lucia, Soufrière and many more! See Saint Lucia and the historic center of Bridgetown and its garrison and tour the Grenadine Islands - one of the world’s most stunning archipelagos

Top Cruise Deals to the Lesser Antilles for 2020

Trip Name	Save	From	Days	Next Departure	Summary
Grenada Round Trip	$600	$2800	14	Nov 1, 2020	On the S/V Mandalay, experience a Caribbean few others ever see. Partake in raising the sails, take a turn at the helm, or just enjoy the winds of … 0
Leeward Islands	Savings	$2240	8	Dec 12, 2020	The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Nevis, Dominica, … 0
Treasure Islands	Savings	$2240	8	Dec 5, 2020	Soak in the sun in one of the most magical destinations on the planet, the Caribbean. Don’t miss a chance to lay out on one of the beaches and feel … 0
Grenadines	Savings	$2160	8	Jan 2, 2021	Departing from Barbados on this 8-day roundtrip Caribbean cruise aboard the Royal Clipper luxury sailing ship, this relaxing trip through the … 0
Windward Islands	Savings	$2340	8	Dec 12, 2020	Board the luxurious Royal Clipper sailing ship for this 8-day roundtrip cruise of the Caribbean, departing from Bridgetown, Barbados to St. Lucia, … 0
Transatlantic: Lisbon to Barbados	Savings	$2530	17	Oct 22, 2020	Join the Royal Clipper on a fantastic adventure across the Atlantic Ocean from the capital city of Lisbon, Portugal to Barbados, a heaven on Earth. … 0