Good Times Ahead
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Day Sails
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Welcome aboard!
Welcome Aboard Schooner Eastwind & Schooner Applejack, in Boothbay Harbor your Maine Vacation starts here. Join the Schooner crew for a 2hr. day sail, sunset sail or private charter adventure on Boothbay Harbor’s oldest windjammers. Help hoist sails or take a turn at the wheel as we set a course out past Burnt Island Light, Squirrel Island, Ram Island Light and the outer islands of Boothbay. Keep a sharp eye out for porpoise, Osprey, Bald Eagles, and harbor seals as we slip by local boats setting their pots or hauling in the lobster catch of the day.
Why Sail With Us
Our goal is for you to experience the best two-hour classic sailing trip in the world. We have been working on this experience in Boothbay Harbor for almost 50 years, have a strong local following, and have been featured in national, best-selling publications. We have the best sailing vessel for exploring Boothbay Harbor. We use an onboard engine to get us to the sailing grounds quickly. The size of our vessel is perfect for exploring all the areas of our rocky harbor to see life along the Maine coast. There are no obstructions on our deck other than the masts, so you always have a full 360-degree view from every seating position.
Our docks are in the center of Boothbay Harbor’s historic waterfront. You are literally steps away from great inns, shops, restaurants, and other activities on the water. We work with and support our waterfront community and will be happy to advise you on all the great experiences around us. Our long history and focus of providing a great experience has made us the first page of Maine’s official guidebook and the first page of the official region guide to the Boothbay area. We have many people who return year after year from abroad to go out with us multiple times a season.
