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 2026-2027

All Leeward Islands Small Ship Cruises
Visit beautiful Norman Island

Vibes of the Virgin Islands

8 Days from $9,990
Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning beaches of Virgin Gorda, snorkel in Norman Island’s clear waters, and experience Anguilla’s vibrant beauty.
0
Relax on the beaches of St. Maarten

Cruising the Leeward Islands

8 Days from $6,395
Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara, starting in Philipsburg, Sint Maarten. Visit Anguilla's coral reefs, explore Virgin Gorda's grottos, and enjoy local cuisine while discovering unique island architecture.
0
Relax on the beaches of St. Maarten

Leeward Islands

8 Days from $2,010
Join an 8-day roundtrip Caribbean cruise from Philipsburg, St. Maarten, on the Star Flyer, visiting historic Nevis, scenic Dominica, and the vibrant yachting hub of Antigua. Enjoy snorkeling in Terre-de-Haut and explore Basseterre and South Friars Bay in St. Kitts before returning to St. Maarten.
0
Tropical waterfall and turquoise pool in lush forest of Dominica

Treasure Islands

8 Days from $2,010
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
Boats Moored to the Quay at Bridgetown Harbour

Discover the Pearls of the Caribbean

15 Days from $15,980
Embark on a 15-day Caribbean cruise aboard Emerald Azzurra, exploring stunning coral reefs, granite pools, and picturesque landscapes across destinations like Anguilla and Virgin Gorda. Enjoy snorkeling, hiking, and vibrant local culture while visiting Saint Barthelemy and the British Virgin Islands.
0
Gustavia Harbor in St. Barths

Cruising the Leeward Islands

8 Days from $9,990
Set sail on an 8-day Caribbean cruise with Emerald Azzurra. Start in Marigot, then visit Anguilla’s coral beaches, Virgin Gorda’s Baths, Jost Van Dyke’s Bubbly Pool, and Anegada’s sandy shores. Explore Saba’s trails and Bonaire’s marine life before ending in Gustavia. Enjoy a luxury cruise with varied landscapes and activities.
0
The Southeast Peninsula of Saint Kitts with Nevis in the Background

Quintessential Caribbean

8 Days from $9,990
Explore the Caribbean on an 8-day cruise from Saint Thomas to San Juan aboard Emerald Sakara. Visit Saint John, Nevis, Guadeloupe, Antigua, Saint Barthélemy, and the British Virgin Islands. Discover UNESCO-listed landmarks, swim in clear waters, and experience regional architecture, food, and history throughout the journey.
0
Relax on the pristine beaches of the Virgin Islands

Tropical Charms of the Caribbean

10 Days from $8,095
Experience a 10-day cruise from Philipsburg, Sint Maarten, aboard the Emerald Sakara, visiting stunning beaches and local markets in Guadeloupe and exploring the British Virgin Islands. Enjoy unique landscapes in Montserrat and relax on Virgin Gorda's beautiful shores before returning to Philipsburg.
0
Learn about Spanish colonial history in Old San Juan

Caribbean Yachting Discovery

8 Days from $6,745
Set sail on an 8-day Caribbean cruise aboard the Emerald Kaia from Antigua, visiting St. Kitts, Guadeloupe, and Saint-Barthelemy, before exploring the British Virgin Islands' iconic sites. End your journey in San Juan, Puerto Rico, the oldest European settlement in the Americas.
0
Learn about the history of the Caribbean

Across A Sea Of Idyllic Islands

8 Days from $6,995
Sail 8 days aboard Sea Cloud Spirit through the Caribbean’s Lesser Antilles & Grenadines. Discover St. Maarten, Virgin Gorda, Jost van Dyke, Norman Island, St John’s, and St. Barths while enjoying authentic tall-ship sailing and idyllic island scenery.
0
All Leeward Islands Luxury Small Ship Cruises

2 Best Leeward Islands Luxury Small Ship Cruises

Trip Name From Days Summary
Island Odyssey: Bahamas to the Grenadine $19,990 11 Set sail on an 11-day Caribbean cruise from Nassau to Bridgetown on the Scenic Eclipse, visiting remote gems like Staniel Cay, Turks and Caicos, and St. Barts. Enjoy ultra-luxury amenities and guided excursions for a refined and relaxing experience.
0
Cruising the Caribbean's Windward Islands – with Smithsonian Journeys $5,590 8 Embark on an 8-day cruise aboard Le Champlain and explore Saint Lucia, Dominica, Les Saintes, Bequia, Mayreau Island, Tobago Cays, and Barbados. Snorkel coral reefs, swim in turquoise lagoons, discover historic towns, visit beaches, and encounter marine life across the Caribbean.
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

The Leeward Islands in the northeastern Caribbean are a year-round destination. December to April offers sunny weather and festivals, while May to November brings fewer tourists and lower costs. Explore these islands on small cruise ships Caribbean journeys for the best mix of culture, beaches, and local charm.
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

Relax. We've got this.

Talk with an expert trip planner 1.800.344.6118

Plan My Trip
Kevin Moore employee headshot
Kevin M.
Stroll along the beautiful beaches of the Caribbean
Caribbean

Chat Leeward Islands with a specialist

Our team is waiting and ready to talk with you about your next adventure. So go ahead and book an appointment with one of our specialized trip planners.

Let's Chat
1.800.344.6118

Where is your next adventure?

Contact Chat Call

Why Travel With Us?

Advocacy That Matters

You're backed by a team that knows the industry and has strong relationships—helping ensure you're prioritized and well taken care of every step of the way.

Seamless Trip Planning

We guide you through every detail beyond the cruise—from flights to pre- and post-trip stays—so your journey feels effortless.

Unbiased Cruise Expertise

We're not tied to any one cruise line, so you receive honest guidance on the best ship and itinerary for you—not a sales pitch.

As Featured In

USA Today
Los Angeles Times
Travel Weekly
Outside
National Geographic Traveler
The New York Times
Travel + Leisure
Condé Nast Traveler
National Geographic

How it Works

Connect

No cost, no commitment. Talk with our experts about your dream trip.

Plan

Share your travel style—we match you with the right itinerary or create one just for you.

Book

Lock in knowing every detail is handled and you’re fully supported.

Travel

Enjoy a seamless journey—and unlock 5% off your next adventure.

Kevin Moore employee headshot
Kevin M
Plan My Trip
We love travel, talk with an expert 1.800.344.6118