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Windjamming is Maine's Best Kept Secret
for almost 90 Years

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Did You Know?

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Try a Different Vacation

Grace Bailey

An Experience Not to be Missed

"The boat was immaculate, the food was incredible, and the crew were great. We've sailed around Maine before, but this experience was the best ever."

GRACE BAILEY is THE way to Experience Maine 

How our trips are different

You get to explore the coast of maine under sail!  Picture yourself aboard a large, traditional schooner, gliding among the protected waters of nearly 700 islands.  

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Maine sailing is for everyone! Even if you have never sailed before.


Do you want to relax and read a book in the sun? While away your time between freshly made meals and dessert? There is no better setting than our historic schooner and the coast of Maine. 

Do you want to get the most out of your Maine vacation?

Spend your nights aboard in calm, serene 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. 

Our trips offer options to fit everyone's taste, while always being unique and enchanting!

Do you want to help hoist the sails and learn all about traditional sailing? Have at it. Do you want to just sit back and watch it all happen? No problem. There's lots of space and the view is always changing. Any questions?

We even have small boats we can take you out in once we anchor, or you take one out on your own! Our trips are a unique and authentic Maine experience to get the most out of your vacation. 

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by George Borne

Enjoyable & Easy

"We provide a very accessible way of experiencing Maine. You don't have to learn some special skill to sail with us. You don't have to hike to be here. You don't have to drive from place to place to see the sights. 

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From great meals, to going ashore, to small boat sails, we handle it all."


- Captain Sam Sikkema

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.

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 the Operations Manager and co-owner of Grace Bailey. In addition to her enthusiasm for the Maine Coast and sailing, Suzannah enjoys winters of skiing and ice skating nearby her home in Thomaston.

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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.

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. 


Not only is Maine beautiful, it's delicious. Local cuisine is a wonderful way to add to your authentic Maine experience. 

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


Of course, every Grace Bailey sail also includes a traditional New England all-you-can-eat Lobster dinner.

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Learn the History

Grace Bailey is a sailboat with a very special heritage.  Constructed at Patchogue, Long Island in 1882, she is an authentic American lumber-carrier, directly from the age of sail. 


After decades of efficiently transporting yellow pine along the Eastern Seaboard, Grace Bailey then also proved fast enough to carry perishable foods and fruits to and from the Caribbean.

During the World War II era, Grace Bailey honored our nation as the primary sail-training vessel of Maine Maritime Academy, famously located in Castine, still among our cruising grounds.


And today, Grace Bailey’s 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!

"One of the reasons why I like the historic vessels is that historic connection; trying to imagine achieving something with this vessel that's not just sailing.

The sailing was the means to an end. These boats hauled cargo to build this country. That end, those buildings, are something you can connect with.  You've likely stood on the granite steps to some courthouse somewhere that these boats hauled.

That connection is unique to historic vessels like GRACE BAILEY." 

- Captain Sikkema

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GRACE BAILEY has the space to relax and the size to offer smooth sailing. This makes her a fun and comfortable sailboat for couples, families, and charter groups.  

Aboard our schooner is THE way to explore the best of Maine's rugged beauty. This bold, new perspective makes our trips different. These trips stand out. You will remember them for the rest of your life. We guarantee it. 

Do you want the best
of Maine?

Your days will be filled with sights you cannot see any other way. We call this Secret Maine. 


Many guests return to see different parts of “Secret Maine” each year!  You will feel the same way. 

There are 700 stunning islands in our cruising grounds. They provide serene natural shelters for our nightly anchorages. 

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

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