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.

Sails up. Phones down. Coastline ahead.Stay connected for the latest specials and events, follow us Boothbay Harbor Sail...
09/02/2026

Sails up. Phones down. Coastline ahead.

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

The sails come down, the sky turns that color, and suddenly nobody is checking the time.Our sunset sails give you two ho...
09/01/2026

The sails come down, the sky turns that color, and suddenly nobody is checking the time.

Our sunset sails give you two hours on the water to take in the Maine coast, lighthouses, islands and whatever Mother Nature decides to add to the show.

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

Blue skies, sparkling water, and nothing but the Maine coast ahead. ⛵️Sometimes the best part of sailing is simply slowi...
08/26/2026

Blue skies, sparkling water, and nothing but the Maine coast ahead. ⛵️

Sometimes the best part of sailing is simply slowing down and taking in the view. From the deck, Boothbay Harbor hits a little differently.

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

Date night idea: trade dinner reservations for ocean views. ⛵️💙Grab your favorite person and spend a few hours sailing t...
08/25/2026

Date night idea: trade dinner reservations for ocean views. ⛵️💙

Grab your favorite person and spend a few hours sailing the Maine coast together. Fresh air, beautiful views, nowhere you need to rush off to… Sounds like a pretty good date to us.

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📍 Harbor Maine
🗺️ maine

Throwback Thursday to one of those photos that never gets old. ⛵️Full sails, golden light, and the Maine coast in the ba...
08/20/2026

Throwback Thursday to one of those photos that never gets old. ⛵️

Full sails, golden light, and the Maine coast in the background. There’s something timeless about seeing a schooner out on the water and this shot captures it perfectly.

Some views are worth revisiting. 💙

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📍 Harbor Maine
🗺️ Maine

There’s just something about a day on the water. ⛵️🌊Good company, salty air, big smiles, and the beauty of Boothbay Harb...
08/18/2026

There’s just something about a day on the water. ⛵️🌊

Good company, salty air, big smiles, and the beauty of Boothbay Harbor all around you. These are the kind of Maine memories we love being part of.

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

⭐ ⭐ ⭐ ⭐ ⭐ TripAdvisor Review: "Entirely delightful & calmed all nerves!We had the best time with captain Josh! Our mom ...
08/13/2026

⭐ ⭐ ⭐ ⭐ ⭐ TripAdvisor Review: "Entirely delightful & calmed all nerves!
We had the best time with captain Josh! Our mom was sooo nervous before going on and Josh made everything so comfortable and easy. He was informative and entertaining as well to hear more about sailing, the area and all the amazing things at boothbay harbor!" -Sarah

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

There’s just something about seeing these beauties out on the water. ⛵️Full sails, open water, and a Boothbay Harbor sum...
08/11/2026

There’s just something about seeing these beauties out on the water. ⛵️

Full sails, open water, and a Boothbay Harbor summer doing what it does best. Who’s ready to sail with us?

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

Happy Friday! ⛵✨Leave the week behind and let the wind carry you into the weekend. There's no better place to recharge t...
08/07/2026

Happy Friday! ⛵✨

Leave the week behind and let the wind carry you into the weekend. There's no better place to recharge than out on the water with the sun on your face and the sails overhead.

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

Every sail offers a different view... and every view tells a story. ⛵💙Out on the water, nature has a way of reminding us...
08/05/2026

Every sail offers a different view... and every view tells a story. ⛵💙

Out on the water, nature has a way of reminding us to slow down, look up, and soak it all in. Every sail offers a front-row seat to moments like these—and no two are ever the same.

⛵ Come see what awaits beyond the harbor.

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

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