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footage by Jeremy T. Grant

by George Borne

All - Inclusive, unique, enchanting

3 - 6 night Maine Vacations

Spend your nights aboard in calm, beautiful coves. Relax in front of a sunset, or under brightening starlight with a glass of wine. You will appreciate the difference of our trips - from any other vacation. 

THE way to experience Maine. 

Picture yourself aboard  our charming and sizable, traditional schooner, gliding among the sheltered waters of nearly 700 scenic islands.  

Captain Sam Sikkema

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Having sailed the world on all manner of vessels, his favorite sailing grounds are the waters of Penobscot Bay, here in Maine. Sam has a trove of knowledge about the traditional side of sailing.  He is also a maritime history buff. He has had a passion for sailing since childhood. Sam has not only circled the world’s oceans as an intrepid blue-water navigator, but he is a sailmaker of authentic canvas sails and rigging for all types of historic vessels.  During your trip, Sam will introduce you to the craft and tradition of sailing.

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Marc Evan Jackson

Marc Evan Jackson is an actor known for his roles on Brooklyn Nine-Nine, The Good Place, Parks & Recreation, The Baby-Sitters Club, and many more. Thirty years ago, long before he was in Hollywood, Marc was the first mate of the GRACE BAILEY's former sister ship, the schooner MERCANTILE. Marc is thrilled to be keeping the tradition alive, and can't wait to share the magic of schooners, windjamming, and Maine with old salts and newcomers alike.

Meet Your Hosts

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Suzannah Smith

A Mainer born and raised, Suzannah grew up in the coastal town of Brunswick. Some of her fondest memories as a youngster were weeklong family sailing trips downeast around Penobscot Bay. Suzannah graduated from Bates College in Lewiston, Maine with a passion for environmental studies and sustainable food systems. After a few years of engaging work in farms and restaurants across Maine and New Orleans, she found herself back in Penobscot Bay as galley hand on a Windjammer and fell in love with the maritime industry. With some valuable crewing time under her belt, she moved to a permanent shoreside position with the historic Windjammer, Victory Chimes and quickly gained responsibility. Today, she is thrilled to be a co-owner and manager of the Grace Bailey.

Gray & La





Meet Our Guests

Watch fun videos of our guests talking about their trips. More here

Amazing Vacation on the Water

""I'’ve never been on a ship before, so I wasn’t sure what to expect, but this trip was magical!


Waking up to amazing vistas every morning, enjoying coffee and a pastry on the deck, feeling the ship under sail and getting to help raise them, all incredible.


Honestly, the only downside is that the food was so good I ended up gaining 5 lbs. Exceeded expectations, would go again. And again. And again."

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Sail the world-renowned sheltered waters of Maine's Penobscot Bay.


Always in sight of land, weaving through the coastal archipelago

Savor the Cuisine

Homemade meals are a big part of our Windjammer experience.  Our all-inclusive trips provision our menu through a small collection of local Maine vendors for an authentic, Maine experience. 

Serene coves, delicious wines, dazzling sunsets. This is the way to experience the best of Maine. 

You’ll enjoy daily, delectable charcuterie boards, scrumptious apps, family-style meals, and tempting desserts.


Every trip also includes a traditional New England all-you-can-eat Lobster bake on a beach!

Learn the History

GRACE BAILEY is an authentic American lumber-carrier, directly from the age of sail. She was built in Patchogue, Long Island in 1882.

Today, her rugged design translates directly into broad and uncrowded decks.  With an incredible 24’ beam (width), you’ll find the comfort and space to sunbathe or just take in island views!

Have Maine All to Yourself.
Book a Private Charter.

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