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!

Maine Windjammer Cruises is the original Windjammer Fleet established in 1936. First to offer the opportunity to sail Maine coast waters aboard former cargo schooners, our National Landmark …

Sep 25, 2025 · What exactly is a "windjammer" cruise? We break down the definition of these tall ship sailings and what you need to know before you book.

Set sail on a Windjammer cruise in the Caribbean, where you’ll enjoy traditional sailing, stunning vistas, and an unforgettable journey.

Windjammers begin sailing in late May and end in mid-October. You can also find each vessel’s schedule by visiting their fleet page. We found 218 sailing adventures. Lighthouses! Trying to book …

Embark aboard Schooner Heritage on an all-inclusive Maine Windjammer sailing vacation. Sail across the glistening waters of Mid-Coast Maine for pure bliss and enchanting coastal discovery.

Experience the grandeur of tall ship cruises with Island Windjammers. Unleash your inner explorer and book your sailing adventure today!

Welcome to the Maine Windjammer Association – the largest fleet of traditional tall ships in the Americas. Our iconic windjammers offer multi-day, all-inclusive, sailing adventure cruises in one of …

Please select a month on the calendar and click on your desired boarding date (Sunday, Wednesday or Friday) to see available cruises. You can also use the drop-down menu to select a specific length of …

Sail aboard the Sea Cloud, one of the finest windjammer sailing vessels operating today. Enjoy luxurious sailing cruises with 64 passengers & a crew of 60.