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

Did You Know?

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."

 Never been to Maine? Discover why it's called "Vacationland." If you have been to Maine before - lucky you! - you're going to explore "Secret Maine" this time; experience it deeper; find hidden gems, connect with people; chase the magic. That is what our trips are all about. 

You will remember your vacation for the rest of your life. We guarantee it. 

How our trips are different

Connect with People

When a bunch of people gather to connect with nature, something magical happens; they connect with each other. 

There is no other vacation that plants the seeds of fellowship and camaraderie like ours. 

The ship allows for solitude. The experience promotes togetherness. 


You will meet interesting people. The connections will be special. 


"That's exactly what sailing is, because you cannot get around it. You have to work with it. You can work with the environment around you to achieve doing something interesting and different. And we get to do it in beautiful settings that you can't see any other way."

 - Captain Sikkema

Connect with Nature

"We provide a very accessible way of connecting to nature. You don't have to learn some special skill to be on the boat. You don't have to hike to be here. When you come aboard, you can feel how the boat works with the natural elements and connect to it."

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"These moments can come after we're done sailing for the day too. A quiet summer night, with the long sunset and the last colors in the sky. And the lanterns flickering all around, and people chatting; It feels magical."

- Captain Sikkema


Sailing provides a direct connection to nature. We have to be in tune with nature to get the ship to move. There's no way around it. 

Tons of ship, moved by wind, and easily. When the sails fill, you will feel the power of that connection. It feels like magic. 

The wind guides our trips. We do not have a set itinerary. We chase the best winds. We chase the magical feeling of that connection.

Our Trips are about Connection

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Connect with Cuisine

Local cuisine is a memorable way to connect to a place. We provision through a wide collection of local vendors to spoil you with Maine goodness. 

You'll enjoy delectable charcuterie boards, delicious family style meals and tempting desserts.

Shared meals are also a great way to connect with your fellow travelers. Food is fellowship. 


Not only is Maine beautiful, it's delicious. Every trip includes an all-you-can-eat Lobster dinner! 

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Connect with History

Few things can connect you to history like a boat that's still making history. 

Built in 1882, by shipwrights that were alive during the Civil War, GRACE BAILEY has seen a lot. The charm and historicity of such a vessel is alluring.

The coast of Maine still looks as it did a hundred years ago; granite shores and regal pines. Being immersed in that scenery, aboard one of its proud ornaments, is a special feeling, with a deep connection. 


Maritime culture is alive and well in Maine and this boat is one of its proud ambassadors. 

"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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