Maine Windjammer Boat Tours and Cruises

True seafarers say the best way to see Maine is from the sea. We agree. Once you have watched a golden Maine sunrise from the deck of a windjammer, surrounded by the blue Atlantic waters, you will never forget that magical moment. For those looking to safely dock their windjammer, you can find many transient marinas in Maine.

Maine windjammer tours and boat cruises allow you to explore the coast from the best vantage, by boat. Maine’s jutting coastline is over 3,500 miles long with dramatic rocky peninsulas and hidden coves and inlets. There are numerous Maine sailing charter companies, you can choose from. See below for windjammer cruises.

Maine Windjammer Parade

Most Windjammer companies are very accommodating and can take you to nearby islands or just a cruise to nowhere so you and your yachting guests can enjoy the scenery and the Maine wildlife.

Windjammers charter 2, 3, 5 and 7 day Maine Coast cruises. Imagine a week long sailing vacation on an historic tall ship, sleeping to the calming sound of the waves and the mast swaying, and waking to sunrise over the Atlantic and fresh breakfast prepared by your yacht’s crew.

Sailing in Casco Bay, or a charter in Penobscot Bay from Camden or Rockport, are great places to start your Maine windjammer sailing adventure. Your captain might drop the hook, and anchor off the shores of Vinalhaven, home to lobster fisherman and fishing author Linda Greenlaw who wrote about the Perfect Storm in her book “The Hungry Ocean”.

Boothbay Harbor is another sailors’ gem with beautiful coves and islands, and many charters leaving the piers on Boothbay’s waterfront


Bar Harbor, and nearby Southwest Harbor on Mount Desert Island, are boatbuilding and sailing capitals of Maine. You can take a sailboat tour out of Bar Harbor, or a wooden schooner charter from Southwest Harbor near Acadia National Park.

Maine Windjammer sailing vacations are generally all-inclusive packages – your yacht lodging, three homemade meals a day, and sailing instructions are all part of your sailing charter package. Of course, the spectacular Maine scenery is always included in your schooner charter.

Maine Windjammers Boat Tours and Cruises

Schooner American Eagle | Captain Tyler King | Rockland, ME

Windjammer Angelique | Captain Dennis Gallant & Candace Kuchinski | Camden ME

Schooner Grace Bailey | Captain Sam Sikkema | Rockland, ME

Schooner Heritage | Captains Sean Grims & Ben Welzenbach | Rockland, ME

Schooner Ladona | Captain J.R. Braugh  | Rockland, ME

Schooner Lewis R. French | Captain Becky Wright and Nathan Sigouin | Camden, ME

Schooner Mary Day | Captain Barry King and Jen Martin | Camden, ME

Schooner Stephen Taber | Captain  Noah & Jane Barnes | Rockland, ME

All of the above windjammers are part of the Maine Windjammer Association.

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