Top Portland Sailing

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds (NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites). Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. All ages are welcome! Whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the beauty and serenity of the rugged coastline as you gaze upon seabirds, sea houses, and islands. Guests are encouraged to help raise the sails with a deckhand and steer the ship for themselves. Your charter is your time to relax, celebrate, entertain, and sail, so you get to set the pace and atmosphere. Beer, wine, and other alcoholic beverages are permitted on board.