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 windjammers continue to provide affordable all inclusive sailing vacations.

Our iconic windjammers offer multi-day, all-inclusive, sailing adventure cruises in one of the most acclaimed cruising grounds in the world. When you sail aboard a Maine Windjammer Association vessel, you can be sure that your hosts hold themselves to the highest standards of …

EXPLORE OUR OVERNIGHT CRUISE SCHEDULES & PLAN YOUR TRIP TODAY! The intimate 6-passenger Swift offers the joys of sailing and socializing in a smaller modern setting. Our online reservation system is ready for your reservations, but we can also take reservations by phone. We love speaking with our passengers!

Choose from one of our breathtaking cruises below! Our 3 and 4 night cruises board on Sunday and Wednesday evenings. Weekend cruises board on Friday afternoons. Charters are …

Use the “Book My Trip” box above to search for cruise dates. Windjammers begin sailing in late May and end in mid-October. You can also find each vessel’s schedule by visiting their fleet page. 217 sailing adventures found. Spring sailing! Trying to book last minute? You can find cabin availability on each vessel’s website.

Discover the magic of a windjammer cruise on Penobscot Bay. Our sailing excursions offer fresh cuisine, views of marine life, lighthouses, and more.

There’s no better way to experience Maine’s scenic coastline than a Windjammer cruise aboard the historic Schooner J. & E. Riggin. Your 3-, 4-, 5-, or 6-night sail departs from Rockland, Maine, and will take you along the bold and beautiful granite coastline, past spruce-clad islands, and through the legendary lighthouses-dotted points of ...

MAINE WINDJAMMER CRUISES ~ Maine's Original Schooner Company operating in Camden, Maine since 1936. Our luxury schooner Swift provides affordable all-inclusive sailing vacations on Penobscot Bay. Take a turn at the helm, lend the crew a hand or sit back and…

Our Windjammer cruises combine the beautiful coast of Maine with tremendous sailing aboard an historic tallship....not to mention the homemade cuisine and all-you-can-eat-lobster! From Memorial Day through mid-October, we sail from Camden Harbor along Maine’s pristine coast, sharing the Lewis R. French with only 20 guests on each trip. Spend ...

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. Whether your a solo traveler or group of friends looking for adventure and relaxation, or a couple looking for that Romantic getaway in Maine, sail aboard ...