Island Windjammers
Escape. Explore. Exhale. Unique, small-ship cruising adventures throughout the Caribbean, Greece & Croatia since 2009.
Island Windjammers Instagram
Island Windjammers Instagram
Island Windjammers Facebook
Island Windjammers Facebook
Island Windjammers YouTube
Island Windjammers YouTube
SAIL DIAMANT BY DATE
SAIL DIAMANT BY DATE
SAIL DIAMANT BY DATE
Diamant offers an intimate classic Caribbean sailing experience for just ten guests, blending traditional charm with barefoot adventure. Enjoy relaxed days on sparkling waters, quiet anchorages, and warm camaraderie. With cozy cabins, personal service, and itineraries shaped by wind and whimsy, every voyage reveals authentic…
SAIL DIAMANT BY ITINERARY
SAIL DIAMANT BY ITINERARY
SAIL DIAMANT BY ITINERARY
Book directly online with live availability, whether you're at a computer or on the go.
POPULAR - LAST CABINS
KLARA: XMAS & NYE DEC 19 2026
KLARA: XMAS & NYE DEC 19 2026
KLARA: XMAS & NYE DEC 19 2026
ESCAPE: View our Fleet
ESCAPE: View our Fleet
ESCAPE: View our Fleet
Browse all of our sailing cruises in the Caribbean, Croatia, & Greece to enjoy a relaxing on-the-water experience with us at Island Windjammers! Book a cruise now!
EXPLORE: Greek Sailing Cruises
EXPLORE: Greek Sailing Cruises
EXPLORE: Greek Sailing Cruises
Lyra has been sailing the sun-drenched Greek Isles since 2023, offering effortless style, modern sophistication, and the easygoing spirit that defines every Island Windjammers adventure. Choose 6- or 10-night voyages through ancient Greece, for a sail as old as time.
EXPLORE: Caribbean Sailing Cruises
EXPLORE: Caribbean Sailing Cruises
EXPLORE: Caribbean Sailing Cruises
Experience the joy of sailboat cruises with Island Windjammers. Embrace the adventure and book your Caribbean journey today!
EXPLORE: Croatia & Montenegro Sailing Cruises
EXPLORE: Croatia & Montenegro Sailing Cruises
EXPLORE: Croatia & Montenegro Sailing Cruises
Meet Leda: a groundbreaking, zero-emissions, three-masted sailing yacht redefining small ship cruising. Launching in 2027, Leda exclusively invites you to experience premium sustainable voyages through the Adriatic. Sailing from Split and Dubrovnik to secret treasures of Croatia and Montenegro, Leda will set new standards for…
EXHALE: About IWJ
EXHALE: About IWJ
EXHALE: About IWJ
Learn more about Island Windjammers, a premier Caribbean and European cruise line offering unforgettable voyages. Discover our story now!
Virtual Sail our Website
Virtual Sail our Website
Virtual Sail our Website
At Island Windjammers, you can enjoy an unforgettable on-the-water experience with our sailing cruises in the Caribbean, Greece, & Croatia today! Book a cruise now!
Join our Mailing List
Join our Mailing List
Join our Mailing List
Small-ship sailing in the Caribbean, Croatia & Greece plus exclusive sails & best rates.
Registered Travel Agents Join Here
Registered Travel Agents Join Here
Registered Travel Agents Join Here
Shop IWJ Merch
Shop IWJ Merch
Shop IWJ Merch
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