Schedule & Rates
Experience the Maine adventure that you’ve been searching for……
With a variety of 3 to 6-night trips, enjoy the beautiful islands, delicious food, and spectacular sailing that make a trip on a windjammer a memorable experience. No matter how long you are aboard, you will have good food, stunning scenery, memorable moments and great people.
Give us a call or send us an email to learn more about the specific availability of any of our trips to see what will work in your calendar. We look forward to hearing from you!
May-June
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Put Those Paint Brushes, We’re Going Sailing!
The first trip of the season! Come aboard and let’s get everything in full swing. Come be the first to see Penobscot Bay and the schooner welcome in the warm weather.
$998 Per Person Rate
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Enjoy the sailing weather as the change of season brings a good strong breeze. Explore quiet anchorages before the summer season in full swing.
$998 Per Person
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This trip is full.
Join us on this 5-night adventure with modern folk group Reese Fulmer and the Carriage House Band. One evening we’ll raft up with the entire windjammer fleet for an evening together. With informal music sessions throughout the trip it is the perfect addition to sailing alongside spruce-studded islands or anchoring in quiet coves.
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Enjoy the quiet anchorages and beautiful bays we call home—the perfect mix of sailing and shoreside exploring.
$1,208 Per Person
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A perfect sailing getaway over the longest days of the year--plenty of daylight to explore Penobscot Bay on an original Gloucester Fishing Schooner.
$1,208 Per Person
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The perfect oportunity to experience Coastal Maine in so little time! Two days of sailing and a quintessential lobster bake on a quiet beach; what could be better?
$1,058 Per Person
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Booked for Private Charter
Three nights of exploring Penobscot Bay before gathering with the Windjamming fleet for the largest annual gathering of traditional sailing vessels in North America. The festivities begin the evening before leading to the Great Schooner Race full of great sailing and sportsmanship.
July
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Matt and Erica of Darlin Corey join us once again adding so much to our adventures. Music and sailing go hand in hand, with infomal sets throughout the days and evenings. Join us for a truly memorable experience.
$1,396 Per Person
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The perfect trip to explore the hundreds of islands or villages our cruising grounds have to offer. Hiking is anything from an easy stroll to a bit of rock scrambling with water views around every corner! If hiking is not quite to your taste lounge on the many pocket beaches, wade in the tidepools, and take in the beautiful surroundings.
$1,396 Per Person
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A chance to go beyond our normal cruising grounds visiting anchorages a bit farther from home.
$1,546 Per Person
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The Quintessential Windjamming Experience
The perfect oportunity to experience Coastal Maine in so little time! Two days of sailing and a quintissential lobster bake on a quiet beach; what could be better?
$1,246 Per Person
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Six Nights and No Itinerary!
A classic Maine Windjamming adventure: six nights and no itinerary. Lets see what we can see and where we can go! Isle la Haut? Mt. Desert Island? Who knows?
$1,696 Per Person
August
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Explore the Islands of Penobscot Bay
The perfect trip to explore the hundreds of islands or villages our cruising grounds have to offer. Hiking is anything from an easy stroll to a bit of scrambling with views around every corner! If hiking is not quite to your taste lounge on the many pocket beaches, wade in the tidepools, and take in the beautiful surroundings.
$1,396 Per Person
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A unique retreat with guided yoga and mindfullness sessions in the morning or evenings. The perfect setting to practice your skills of balance, control, and relaxation.
$1,246 Per Person
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Booked for private charter
A simple short getaway: three days of sailing and time to explore a coastal village or deserted island, all on a beautiful Gloucester Fishing Schooner.
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The perfect trip to explore the hundreds of islands and villages our cruising grounds have to offer. Hiking is anything from an easy stroll to a bit of rock scrambling! If hiking is not quite to your taste lounge on a pocket beaches, wade in a tidepools, or take in the beautiful surroundings.
$1,396 Per Person
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From spruce covered islands to fishing villages with stunning views all around there is much to fill each moment. A fraction of the cost of chartering your own vessel!
$1,246 Per Person
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Our annual trip home for both the Eagle and Capt. King. A long haul adventure along a classic portion of the east coast. See visiting schooners and experiance over 400 years of history of America's oldest fishing port from the deck of one of its last surviving fishing schooners. All culminating in our chance to win the Esperanto Cup once again!
$2,506 Per Person
September-October
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Woodenboat Magazine is our gracious host for the final Windjammer fleet meet-up. A gathering for an evening on their stunning grounds with the anchorage full of beautiful windjammers is a fine way to send off the season in style. Local photographers Sean and Tracy Sheppard join coach you on how to capture the beauty of Maine.
$1,578 Per Person
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Booked for private charter
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Drank the Gold joins us for a misty sojourn through the isles of Penobscot Bay . Watch the fall foliage begin to change during the day and in the evening cozy up in our wood-paneled galley to a concert of Celtic melodies.
$1,128 Per Person
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Booker for private charter
Come see the foliage change from it's most striking side; the ocean! Between our galley woodstove and our main cabin stove feeding our cabin hallway radiators, there is no shortage of warmth aboard. Fall sailing in Maine is stunning.
$1,128 Per Person
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Thank you all for another phenominal season! Join us as Reese Fulmer plays our 2025 season out. Come join us for one last turn around the bay before we put the Eagle to bed for the winter. We'll dry our sails and have one more chance to visit a couple of our favorite anchorages.
$998 Per Person
Booking and Cancellation Policy
All our cabins accommodate two; Cabins A and B can be guaranteed as single occupancy for an additional $30 per night. 35% of your trip cost is due at the time of booking with the balance due 6 weeks before the trip date. A full refund, less $50 per person fee, will be provided until the balance-due date. Should you cancel with less than six weeks’ notice, your payment less the $50 fee will be refunded if a new guest books in place of your cancellation. Re-bookings are subject to a $50 per-person fee.
Payment Methods
Payments may be made by check, Visa, MasterCard, Discover, or American Express.