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Do Windjammers still exist? Ayuh, you bet they do!

Since the 1930s when Windjammer cruises first started here in Maine, they’ve been growing in popularity. However, since one Caribbean company, Barefoot Windjammers, went out of business, there’s been confusion about which Windjammer companies are still operating. Well, in Maine alone there are 12 Windjammers operating out of Camden and Rockland.  And, there are Windjammer cruises offered in other areas of the country as well. You can take a Windjammer cruise in Maine or the Caribbean or even in Michigan on the Great Lakes. Here’s a list of Windjammer cruise opportunities in the United States and the Caribbean.

Photo by Fred LeBlanc Windjammers sailing along the Maine coast.

Windjammer Cruises in Maine

The Maine Windjammer Association is the largest fleet of tall ships in the Americas. These Windjammers offer multi-day, all-inclusive, sailing adventure cruises on the protected coastal waters of Maine. Cruises are based out of Camden and Rockland, Maine, and sail among the myriad islands off the Maine coast.

Another Maine Windjammer company is Maine Windjammer Cruises. This company sails out of Camden, Maine, and owns three vessels of varying sizes that offer overnight cruises similar to those of the Maine Windjammer Association.

The newest Windjammer business is Canvas and Pine Sailing which operates the Pilot cutter Hesper. The Hesper is a traditional sailboat that can take up to six guests on overnight cruises out of Camden, Maine.

If you’re in Maine but  just can’t get away for a multi-day sailing adventure, you can still sail away for a few hours on a daysailing schooner.  All along the coast of Maine there are traditional sailboats offering two-hour cruises. In Bar Harbor you’ll find Downeast Windjammer Cruise Lines which offers daysails on the schooner Margaret Todd. Towns such as Portland, Camden, Rockport, Rockland, Belfast, and Boothbay also have lots of short sailing options.

Windjammer cruises in other parts of New England

Unfortunately there currently aren’t other Windjamming options in New England. Until 2022 there were Windjammer cruises offered out of Connecticut aboard the Mystic Whaler.  Captain John and Pat Eginton, the boat’s former owners, ran trips for 38 years and in late 2021, after a rich 38 year career, the couple retired. The boat was sold to the Santa Barbara Maritime Museum where it will be used for education programs.

Windjammer cruises on the Great Lakes

The Traverse Tallship Company offers overnight Windjammer cruises on the Lake Michigan. It operates the Schooner Manitou, which is a 114 ft replica of an 1800’s “coasting” cargo schooner. Most of the summer the Manitou offers day sails but in September it offers three to five-night Windjammer cruises.  The schooner sails out of Traverse City, MI. 

Windjammer cruises in the Caribbean

As you probably already know there are tons of sailing options around the Caribbean from chartering small private sailboats to two-hour daysails but in you’re looking to sail away on a Windjammer there are a few choices.

The Liberty Fleet offers daysails in Boston Harbor during the summer and offers overnight Windjammer cruises in the Bahamas in the winter. Their flagship is the Liberty Clipper, which is a 125 ft schooner that carries 24 guests. Their windjammer cruises start and end in Nassau and sail among the outer Bahamas islands such as Eleuthera and the Exumas.

Island Windjammers offers overnight Windjammer cruises from a variety of Caribbean islands. They run two sailing vessels – the smaller Diamant which takes 10 guests and the larger Vela that accommodates 26. Depending on when you sail, the cruise could leave from St. Lucia, St. Kitts, St. Maarten, Grenada, the British Virgin Islands or Turks and Caicos. 

Another company that may turn up when you start looking around for Windjammer cruises is Windstar Cruises. They have a fleet of small cruise ships and large sailing yachts. Their cruises specialize in the luxury experience and even have computer operated sails to do the heavy lifting. These trips aren’t really Windjammer cruises, but if you’re wanting a luxury boating experience in the Caribbean, the Mediterranean, parts of Europe or even Oceania, check them out. 

Now, if you’re still wondering what a windjammer even is, check out our blog: “What is a Windjammer, anyway?”


Categories: Fleet, Maine Windjammers

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