Sail Grace Bailey

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

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

Peaceful moments in the galley 📷 Lena Albert
07/26/2026

Peaceful moments in the galley

📷 Lena Albert

If you’d believe it, yesterday was our 50th lobster bake without going to the same beach twice. That’s almost three seas...
07/10/2026

If you’d believe it, yesterday was our 50th lobster bake without going to the same beach twice. That’s almost three seasons without repeating the same bake spot! Maine has so many amazing unique spots to explore along the coast. Thanks to the Maine Island Trail Association and the Maine Coast Heritage Trust, their knowledge helps us find out where we can drop our anchor and eat some lobster! Here are a few shots from some of the places we’ve been able to explore!

📷 Lena Albert

Cheers to a fun Race Day and a Happy Fourth of July!! 📷 Lena Albert
07/04/2026

Cheers to a fun Race Day and a Happy Fourth of July!!

📷 Lena Albert

Come explore the schooner Grace Bailey and get a ship tour- Thursday and Friday June 25th and 26th between 10 am - 2 pm ...
06/25/2026

Come explore the schooner Grace Bailey and get a ship tour- Thursday and Friday June 25th and 26th between 10 am - 2 pm or just come by! We’ll be dockside at Boothbay Harbor Shipyard (Sample’s) for Boothbay Harbor Windjammer Days! Come say hi!!

📷 Hannah Hoggatt

Address

Captain Spear Drive
Rockland, ME
04841

Telephone

+12076919521

Website

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