Sail Grace Bailey

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Sail Grace Bailey We offer 3 to 6 night All-Inclusive, Maine vacations aboard our charming 1882 Schooner.

Another successful season coming to a close! Thank you to everyone who sailed and to all the crew for always doing amazi...
10/20/2026

Another successful season coming to a close! Thank you to everyone who sailed and to all the crew for always doing amazing work!

📷 Lena Albert

Schooner friends are the best friends 📷 Dave Waddell
09/28/2026

Schooner friends are the best friends

📷 Dave Waddell

Happy first official day of fall! 📷 Hannah Hoggatt
09/22/2026

Happy first official day of fall!

📷 Hannah Hoggatt

Teamwork makes the dream work 📷 Lena Albert
09/14/2026

Teamwork makes the dream work

📷 Lena Albert

Fiji on her throne 📷Lena Albert
09/11/2026

Fiji on her throne

📷Lena Albert

The crew is absolutely nailing it this season! 📷 Lena Albert
08/31/2026

The crew is absolutely nailing it this season!

📷 Lena Albert

Sunshine on the bay 📷 Lena Albert
08/19/2026

Sunshine on the bay

📷 Lena Albert

If you’ve already been aboard this season you know her well! We are so excited to have Hailey this season, even if it’s ...
08/05/2026

If you’ve already been aboard this season you know her well! We are so excited to have Hailey this season, even if it’s just for a little while longer!

Hi there! While born and raised in Texas, I came to Maine for the first time this summer to get a taste of windjammer life. I am currently attending the University of Texas at Austin studying environmental engineering, but I decided to trade the textbooks for life under sail this summer to serve as Grace Bailey’s galley hand! Throughout the season, I have worked to perfect my tiramisu and charcuterie boards — which frequently include a double-decker spread and whimsical floral arrangements. When I head back south of the Mississippi, I am excited to reunite with my cat, Leo (don’t tell Fiji), and drop sailing lingo mid-conversation with my friends.

📷 Lena Albert
📷 Hailey Clingan

Address

Captain Spear Drive
Rockland, ME
04841

Telephone

+12076919521

Website

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