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Your Maine sailing vacation starts here!

Photo: Fred LeBlanc

Sail aboard the newest and largest vessel in the fleet!

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Enjoyed the trip of a lifetime with my daughter (age 29)! The Captains and crew were kind and engaging and the food was incredible! The main coast is full of beautiful little islands and sailing felt like such an adventure!
The captains entertained us one evening and surprised us with their notable talents!

Jennifer B

Welcome Aboard!

We hope you'll join us aboard the Heritage this season for an unforgettable Maine windjammer cruise. Every trip is special. Capts. Sean and Ben are your hosts aboard every trip. In addition to sailing the vessel, they enjoy entertaining their guests by playing live music in the evenings. The food is delicious with restaurant quality dishes made with fresh local ingredients. Daily breads, cookies, and desserts are all freshly baked aboard.


Each trip we enjoy an all-you-can-eat lobster cookout on a pristine island beach. Hear about the islands, vessels and people of Mid-Coast Maine as well as the many lighthouses we see. Wildlife abounds with birds both ashore and at sea as well as marine mammals. Best of all you can enjoy sailing aboard a schooner built with your comfort in mind.

Heritage Sailing
Romantic getaway schooner Heritage
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Learning to Sail

We have a trip for everyone aboard the Schooner Heritage. Whether you want to sail with the fleet, explore in search of lighthouses, tour Acadia, bond with family, gaze at shooting stars, or just relax and sail the Maine coast with no itinerary. We can always promise stunning views, delicious food, and an unforgettable experience. Summers in Maine are a time for growth and rejuvenation. The season is short so as Mainers we celebrate and make the most of it. Join us in this celebration as we explore hidden places not accessible to most and with 3,478 miles of tidal coastline, see Maine the way it was meant to be seen.


Coasting schooners, like the Heritage, were designed for accessing shallow passages and ports allowing us to travel to more secluded places where comparable sized vessels can’t access. This makes Heritage the perfect choice when choosing a windjammer to sail on.

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Enjoy an evening beverage and sing along with Captains Sean and Ben during lively music nights. Whether up on deck, or down in the galley, music nights aboard the Schooner Heritage are the best on the bay! 


Performing different genres of music, and the songs you know and love, as well as songs you may have never heard before that will surely be added to your playlist after you get home. 

We look forward to you joining us!

Photo: Nick Parson

Relax  & Unwind

You'll feel like you've stepped into another time and place aboard Heritage. Each day is filled with a little adventure and plenty of relaxation. We leave Rockland headed for parts unknown; wherever the wind, weather, and tides take us. The coast of Maine is spotted with over 3,000 islands topped with lush evergreen forests and lined with rugged granite shores. Row ashore and stretch your legs in local fishing villages and towns rich with art and culture. In the evenings we will anchor in hidden coves where you’ll enjoy coastal wildlife, spectacular sunsets, and endless stars.

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