With Island Windjammers small ship cruises, you’ll experience the Caribbean, Croatia, and Greece intimately, authentically, and under sail. Our fleet offers something for every kind of …

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

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.

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 …

There's no better way to experience the coast of Maine than on a windjammer. Sailing the rocky coast of Maine like generations of Mainers have done will create vacation memories you'll …

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.

Jun 30, 2025 · If you’re planning your first Windjammer cruise, this guide will help you make the most of your trip while answering all your burning questions about this unforgettable experience.

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 …

Maine Windjammer Cruises offers a glimpse into a bygone era when life and recreation were more leisurely. Our schooner sails the Maine coast as the traditional ships did over 100 years …