Boothbay Harbor Sailing

Boothbay Harbor Sailing Welcome Aboard Schooner Eastwind & Applejack in Boothbay Harbor your Maine Vacation starts here. Join the Schooner crew for a 2hr.

day sail or private charter adventure on Boothbay Harbor’s oldest windjammer.

Wind in the lines, another schooner on the horizon, and nothing but blue ahead. This is what a perfect day on the water ...
06/15/2026

Wind in the lines, another schooner on the horizon, and nothing but blue ahead. This is what a perfect day on the water looks like. ⛵ Come find your version of it.

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

Rocky shorelines. Lighthouse views. The kind of scenery that makes you wonder why you ever went anywhere landlocked. Hop...
06/11/2026

Rocky shorelines. Lighthouse views. The kind of scenery that makes you wonder why you ever went anywhere landlocked. Hop aboard a classic windjammer and see it the way it was meant to be seen.

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

Two-hour sails departing Boothbay Harbor, ME all summer long. Some days were made for salt air and open water. 🌊⛵Stay co...
06/09/2026

Two-hour sails departing Boothbay Harbor, ME all summer long. Some days were made for salt air and open water. 🌊⛵

Stay connected for the latest specials and events, follow us Boothbay Harbor Sailing
📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

There’s something special about seeing Boothbay Harbor from the water. 🌊⛵Good company, a sea breeze, and a captain shari...
06/05/2026

There’s something special about seeing Boothbay Harbor from the water. 🌊⛵
Good company, a sea breeze, and a captain sharing the stories that make this coastline unforgettable.

Come aboard and experience Maine the way it was meant to be seen.

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

There’s something special about summer under sail. The breeze feels a little softer, the days stretch a little longer, a...
06/03/2026

There’s something special about summer under sail. The breeze feels a little softer, the days stretch a little longer, and for a few hours, the rest of the world faded away. ⛵☀️ See you tomorrow future adventurer.

Stay connected for the latest specials and events, follow us Boothbay Harbor Sailing
📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

⭐ ⭐ ⭐ ⭐ ⭐ TripAdvisor Review: "Girls day out sailing- beautiful windy day for a sail and Captain Sarah and 1st mate Mor...
05/28/2026

⭐ ⭐ ⭐ ⭐ ⭐ TripAdvisor Review: "Girls day out sailing- beautiful windy day for a sail and Captain Sarah and 1st mate Morrison were perfect hosts on the beautiful Schooner. So much fun!!" -Beth

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

Somewhere between the rigging and the horizon, the rest of the world disappears. ⛵ This is Boothbay Harbor sailing — and...
05/27/2026

Somewhere between the rigging and the horizon, the rest of the world disappears. ⛵ This is Boothbay Harbor sailing — and there's nothing quite like it. 🌊

Stay connected for the latest specials and events, follow us Boothbay Harbor Sailing
📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

Some moments are painted by the sun. 🌅⚓ Golden hour on the water hits different when you're under sail in Boothbay Harbo...
05/19/2026

Some moments are painted by the sun. 🌅⚓ Golden hour on the water hits different when you're under sail in Boothbay Harbor. This is the kind of evening you don't forget.

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

Future captain. No notes. 🧢⛵ We open for the season May 23rd! Bring the whole crew.📸 Mgm_Patrick- thanks for this one!St...
05/13/2026

Future captain. No notes. 🧢⛵ We open for the season May 23rd! Bring the whole crew.
📸 Mgm_Patrick- thanks for this one!

Stay connected for the latest specials and events, follow us Boothbay Harbor Maine USA
📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

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