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
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
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
Caribbean Yachting Discovery$104908Dec 28, 2024Experience a luxurious 8-day Caribbean yacht cruise from St. John’s to San Juan aboard an Emerald Cruises luxury yacht. Discover stunning beaches, …
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
Vibes of the Virgin Islands$75908Dec 13, 2026Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning …
0
Cruising the Leeward Islands$75908Dec 13, 2026Set 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 …
0
Caribbean Yachting Hideaways$71908Dec 7, 2024Embark on an 8-day Caribbean adventure aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches, Vieques’ lovely waterfront, Cruz …
0
Caribbean Yachting Discovery with Chef Ben Robinson$69668Jan 25, 2025Embark on an 8-day Caribbean cruise with Chef Ben Robinson aboard the Emerald Azzurra. Enjoy a welcome reception, cooking demo, and special dinners. …
0
Caribbean Enchantment$63407Feb 22, 2025Embark on a 7-day Caribbean cruise aboard Emerald Azzurra. Start in Antigua and sail to Les Saintes, Deshaies, Virgin Gorda, and Norman Island. …
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
All Leeward Islands Articles

Leeward Islands Travel Guide

Caribbean Travel Guide

Favorite Caribbean Caribbean All Trips

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