Sail Grace Bailey

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

Golden hour through the trees from Little Hen Island in East Penobscot Bay at the entrance of Seal Bay on the eastern sh...
04/30/2025

Golden hour through the trees from Little Hen Island in East Penobscot Bay at the entrance of Seal Bay on the eastern shore of Vinalhaven Island. At low tide, just a short walk from our dreamy lobster bake spot.

📷 Lena Albert

We have our own little library onboard. Whether you want to learn a few knots, do some water color or read about the Mai...
04/28/2025

We have our own little library onboard. Whether you want to learn a few knots, do some water color or read about the Maine coast, we have a great simple selection for you to choose from.

📷 Hannah Hoggatt

The kind of view that stays with you long after the journey ends.📷 Hannah Hoggatt
04/25/2025

The kind of view that stays with you long after the journey ends.

📷 Hannah Hoggatt

Fiji n’ friends 📷 Sean Shepard
04/22/2025

Fiji n’ friends

📷 Sean Shepard

We love this stunning shot from Dave Waddell of us at the Camden Classics Cup a couple of years back!
04/15/2025

We love this stunning shot from Dave Waddell of us at the Camden Classics Cup a couple of years back!

Spring is in the air, and fit out is in motion. 📷 Lena Albert
04/12/2025

Spring is in the air, and fit out is in motion.

📷 Lena Albert

As we sail through summer, we will attend two of Maine’s premier sailing events: Camden Classics Regatta and the Eggemog...
04/08/2025

As we sail through summer, we will attend two of Maine’s premier sailing events: Camden Classics Regatta and the Eggemoggin Reach Regatta. These races honor a rich maritime tradition, showcasing sailing skill, craftsmanship, and the enduring spirit of the sea against the stunning backdrop of Maine’s iconic waters.

📷 Lena Albert
📷 Alex Gorosh
📷 Fred Leblanc / Maine Windjammer Association

July sailing means long days, after dinner swimming, and amazing sunsets! 📷 Jenny Tobin / Maine Windjammer Association
04/04/2025

July sailing means long days, after dinner swimming, and amazing sunsets!

📷 Jenny Tobin / Maine Windjammer Association

Our galley is always busy, but sometimes we get moments like these. Peaceful, quiet, and clean. 📷 Hannah Hoggatt
03/31/2025

Our galley is always busy, but sometimes we get moments like these. Peaceful, quiet, and clean.

📷 Hannah Hoggatt

Maine boasts over 3,000 islands scattered along its rugged, winding coastline. We will set sail through the world-renown...
03/28/2025

Maine boasts over 3,000 islands scattered along its rugged, winding coastline. We will set sail through the world-renowned, sheltered waters of Penobscot Bay, where you’ll always be within sight of land, while weaving through a stunning coastal archipelago.

📷 Alex Gorosh

There’s no-one we appreciate more than our hard working crew. Our crew can definitely be a little goofy, but they know h...
03/22/2025

There’s no-one we appreciate more than our hard working crew. Our crew can definitely be a little goofy, but they know how to get the job done. You will see some of these faces this season as well as some new ones!

📷 Jenny Tobin / Maine Windjammer Association
📷 Lena Albert

The Great Schooner Race is one of our favorite times of the season. A time to get together with our peers and for some g...
03/17/2025

The Great Schooner Race is one of our favorite times of the season. A time to get together with our peers and for some good friendly competition. Get the chance to be apart of the largest annual gathering of traditional schooners in America.mThere’s no feeling like it, experience the excitement and fun of the Great Schooner Race!

📷 Jim Dugan

You never know what creatures you’ll see out on the bay! Birds, porpoise, molas oh my! 📷 Alex Gorosh 📷 Lena Albert📷 Jenn...
03/15/2025

You never know what creatures you’ll see out on the bay! Birds, porpoise, molas oh my!

📷 Alex Gorosh
📷 Lena Albert
📷 Jenny Tobin / Maine Windjammer Association

Comfy and compact! Each cabin is a beautifully designed space blending comfort and elegance all within the hull of a cla...
03/11/2025

Comfy and compact! Each cabin is a beautifully designed space blending comfort and elegance all within the hull of a classic schooner.

📷 Hannah Hoggatt

Address

Captain Spear Drive
Rockland, ME
04841

Telephone

+12076919521

Website

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