Have questions? We're here.
Relax on the beaches of the Caribbean

Leeward Islands Small Ship Cruises

Travel made your way ™
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Talk with an expert
Experience all the Caribbean has to offer as you enjoy a relaxing small ship cruise of the Leeward Islands. Each stop promises an exciting exploration of these sun-drenched islands, with activities like snorkeling in vibrant coral reefs, learning to sail by the power of the wind, getting to know local cultures and their ways of life, diving among tropical fish and even dolphins, or simply relaxing on the golden beaches. Each day brings a host of new activities as you enjoy the tranquil days in the Antilles, in ports on St. Maarten, Nevis, Antigua, Guadeloupe, St. Barth, Anguilla, St. Thomas, St. Kitts, and many others. Contact our Caribbean travel experts to start planning your cruise of the Leeward Islands.
All Leeward Islands Small Ship Cruises

Top 10 Leeward Islands Small Ship Cruises for 2024-2025

All Leeward Islands Small Ship Cruises
Tropical waterfall and turquoise pool in lush forest

Treasure Islands

Philipsburg to Philipsburg
8 Days from $1,640
Don't miss the opportunity to relax on one of the beaches and enjoy the tropical sun's warmth. Soak up the sun in one of the world's most gorgeous locations, the Caribbean. Visit St. Maarten, Anguilla, Jost Van Dyke, St. Kitts, and St. Barts on this 8-day small ship trip!
0
Soak in the sun in colorful Marigot

Cruising the Leeward Islands

Marigot Roundtrip
8 Days from $10,270
Embark on an 8-day Cruising the Leeward Islands aboard Emerald Sakara from Marigot roundtrip. Explore Anguilla, Virgin Gorda, and other stunning destinations, immersing yourself in picturesque landscapes, vibrant cities, and unique natural wonders.
0
Relax on the beaches of St. Maarten

Leeward Islands

Philipsburg to Philipsburg
8 Days from $1,640
The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing 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.
0
Dock going out into the crystal blue ocean

Classic Yachtsman Caribbean

Antigua to Barbados
8 Days from $1,700
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!
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
Stroll along the beautiful beaches of the Caribbean

The Essential of the Caribbean

Fort-de-France Roundtrip
13 Days from $8,150
Sail the lovely seas of the Caribbean roundtrip from Fort-de-France to discover the stunning islands of Antigua, Jost van Dyke, Gustavia, and Portsmouth. Join this 13-day cruise onboard Le Champlain to the heart of the West Indies.
0
Pink beach huts in the Caribbean

Windward Islands

Bridgetown to Bridgetown
8 Days from $1,700
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.
0
White Sand Beach in Barbados

Grenadine Islands

Bridgetown to Bridgetown
8 Days from $1,700
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.
0
Play on the famously beautiful beaches of St. Barth's

Enjoy Caribbean Rhythms at the Turn of the Year

Caribbean: Round-trip Philipsb
15 Days from $11,595
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.
0
St George's Harbor - Grenada

Pearls of the Caribbean

Fort de France to Fort de France
9 Days from $5,430
Join the Le Champlain on its 9-day sailing expedition to explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, Bequia Island and tour the Grenadine Islands - one of the world’s most stunning archipelagos
0
All Leeward Islands Luxury Small Ship Cruises

10 Best Leeward Islands Luxury Small Ship Cruises

Trip NameFromDaysNext DepartureSummary
Treasure Islands$16408Dec 7, 2024Don't miss the opportunity to relax on one of the beaches and enjoy the tropical sun's warmth. Soak up the sun in one of the world's most gorgeous …
0
Cruising the Leeward Islands$102708Nov 30, 2024Embark on an 8-day Cruising the Leeward Islands aboard Emerald Sakara from Marigot roundtrip. Explore Anguilla, Virgin Gorda, and other stunning …
0
Leeward Islands$16408Nov 30, 2024The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Dominica, Iles des …
0
Classic Yachtsman Caribbean$17008Nov 30, 2024Royal Clipper offers the ultimate sea-going experience as you travel to the beautiful beaches and landscapes of the Caribbean. This 8-day sailing …
0
A Colorful Caribbean Time-Out$75008Jan 10, 2025Embark 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 …
0
The Essential of the Caribbean$815013Dec 17, 2024Sail the lovely seas of the Caribbean roundtrip from Fort-de-France to discover the stunning islands of Antigua, Jost van Dyke, Gustavia, and …
0
Windward Islands$17008Dec 14, 2024Board the luxurious Royal Clipper sailing ship for this 8-day roundtrip cruise of the Caribbean, departing from Bridgetown, Barbados to St. Lucia, …
0
Grenadine Islands$17008Dec 7, 2024On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of …
0
Enjoy Caribbean Rhythms at the Turn of the Year$1159515Dec 20, 2024Explore 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 …
0
Pearls of the Caribbean$54309Nov 4, 2024Join the Le Champlain on its 9-day sailing expedition to explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, Bequia Island …
0
All Leeward Islands Articles

Leeward Islands Travel Guide

Fresh produce at a market

Leeward Islands Cuisine

The varied cuisines that travelers enjoy while cruising the Leeward Islands reflect the diverse cultures from which they come, featuring a broad palate of seafood dishes drawing from local Caribbean and African, French, Dutch, British and Asian influences.
0
Explore charming Charlotte Amalie

Leeward Islands Politics

The Leeward Islands, a geographical grouping with an essentially shared history, have developed over time into six separate nations. They have a common interest in tourism, and in economic and cultural advancement for their ethnically diverse but essentially harmonious populations.
0
Stroll along the white sandy beaches of St. Barth's

Leeward Islands Weather

As long as you avoid the hurricane season during the latter half of the year, you'll enjoy pleasant tropical temperatures between 81°F and 95°F (27°C and 35°C) and bright sunny days that never seem to end.
0
Enjoy the natural beauty of the Caribbean

Leeward Islands Geography

Along with the Windward Islands, the small Leeward Islands form the Lesser Antilles on the eastern border of the Caribbean Sea. The geography of the Leeward Islands is comprised primarily by coral and volcanic islands. The soil on the coral islands is not well suited to agriculture, making these countries' primary economic engine tourism.
0
Watch the seas and skies around St. Thomas

Leeward Islands Culture

The cultures of the Leeward Islands are as diverse as the people that inhabit them, coming from many countries in western Europe (like France, the Netherlands, Great Britain, and others) and Africa. Much of the culture ties back into the region's colonial European roots, but there is also a notable presence of unique local Caribbean traditions.
0
TrustScore 4.9 | 209 reviews
TrustScore 4.9 of 5
total score
Based on 209 reviews on
review score
7 hours ago
I have travelled with Adventure Life previously and certainly eager to do it again. Kassandra made excellent and honest suggestions while taking the time to understand what was important to us.
Susan
review score
1 day ago
They answered every question and concern that I had and put me at ease. Very excited for this once in a life-time trip.
Customer Tim
review score
2 days ago
I am a returning client to Adventure Life and am very pleased with their commitment to put together a great trip. Clara replied and clarified to any and all questions we had.
Claire Palmer
review score
4 days ago
Jessica was very responsive to my questions and never balked when I asked her to go back and find more options. She really worked hard to find the right cruise for us.
Amy Siegel
review score
4 days ago
Friendly, accommodating, knowledgeable, timely. They have made us feel very comfortable for our trip!
Gregg Chamberlain

Caribbean Travel Guide

Favorite Caribbean All Trips

Top Leeward Islands Travel Destinations

Leeward Islands Trips by Departure Date

Leeward Islands 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