https://www.facebook.com/106838449047214/

Boothbay Harbor Sailing

Home
United States
Boothbay Harbor, ME
Boothbay Harbor Sailing

Directions

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.

10/27/2026

Straight from 2010, looking like a postcard you’d keep forever. ⛵💙

Full sails, a lighthouse, and those blues. This little gem from the archives has us remembering days on the water and everyone who shared them with us.

Did you sail with us back then? We’d love to hear your memories. 👇

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

10/20/2026

⭐ ⭐ ⭐ ⭐ ⭐ TripAdvisor Review: "Fun sailing trip with Captain Luke!"
"Our party of 6 adults had a great time sailing with Captain Luke in late September. We appreciated getting out on Boothbay Harbor and the peaceful quiet of sailing on the Eastwind. Captain Luke was engaging, funny and safe and also an informative tour guide. The best way to see Maine is from the water and sailing on the Eastwind Schooner was a blast." -LMV

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

10/15/2026

The sails are coming down, but the memories are staying with us. ⛵💙

Thank you to everyone who joined us on the water this season—from familiar faces to first-time sailors. You brought the laughter, the stories, and the company that made every trip through special.

And to our crew: thank you for making everyone feel welcome aboard.

We’ll set sail again in May 2027. Until then, keep a little salt air in your daydreams.

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

10/08/2026

Now that’s our kind of blue-sky day. 💙⛵

Meet . With sails up and views all around, she makes a pretty good case for spending time on the water.

Come see the with us. Explore sailing experiences at boothbaysailing.com.

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

10/06/2026

A little sunshine. A little sea breeze. A whole lot to love. ☀️⛵

Meet , pictured soaking up the sunshine in . Maine looks pretty good from here, doesn’t it?

Explore sailing experiences at boothbaysailing.com.

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

10/04/2026

Sunday called. It said to bring your favorite people and a warm layer. ⛵🍂
Fresh salt air, harbor views, and good company. We could get used to this kind of Sunday.

Who’s coming aboard with you?

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

09/29/2026

Take the helm. ⛵️

There’s nothing quite like the creak of the deck, the pull of the wind, and open water ahead. A little history, a lot of Maine, and one pretty great way to spend a day in Boothbay Harbor. 🌊

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

09/24/2026

The little details of a evening in . ⛵️🌅

Golden light on the lines, salt air off the water, and Boothbay Harbor drifting by.

No rush. No agenda. Just a really good reason to stay out until sunset. 💙

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

09/22/2026

Some sunset sails become part of your story forever. 💍⛵️

What started as an evening aboard Eastwind turned into a proposal—with Captain Matt, First Mate Brian, and 28 fellow passengers there to celebrate right along with Paul and Marla. 🥹

One passenger even captured the moment on video, and their love story went racking up 30,000+ views on !

From strangers to one very enthusiastic proposal crew. 😂❤️ Congratulations, Paul & Marla! We’re so happy got to be part of your story.

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

09/17/2026

POV: Your plans for the day look like this. ⛵️🌊

Salt air, blue skies, and Boothbay Harbor stretching out in front of you. Sometimes the best way to experience Maine is to leave the shore behind.

Come aboard, settle in, and let the wind take it from here. 💙

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

Address

Boothbay Harbor, ME

Website

facebook.com

Alerts

Be the first to know and let us send you an email when Boothbay Harbor Sailing posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Show All