2026 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 company.
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!
Download our 2026 schedule here.
May-June
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Put Those Paint Brushes Down, 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 the bay and help us welcome the schooner into summer.
$1,048 Per Person Rate
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The best music festival you've never heard of!
Join us on this 5- night adventure with the Modern Folk group, Reese Fulmer and the Carriage House Band. The first of our annual Association fleet events, one evening we'll raft up with the entire Windjammer fleet for an evening together. With informal performances throughout the trip, it is the perfect addition to gliding alongside spruce-studded islands or anchoring in quiet coves.
$1,514 Per Person
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From spruce-covered islands to quite fishing villages, a taste of the best of Maine.
Come enjoy the quiet anchorages and beautiful bays we call home, the perfect mix of sailing and shoreside exploring. The perfect addition to any Maine vacation.
$1,111 Per Person
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The best opportunity to experience Coastal Maine in so little time!
A perfect trip for a short adventure on the water. Two days of sailing and exploring Penobscot Bay. The best introduction to windjamming!
$1,111 Per Person
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Celebrate America's 250th in NYC!
Join the American Eagle as we sail back to New York City for the first time since 1986 and join the Sail4th activities. Celebrating the 250th anniversary of the founding of the United States, Sail4th will be the largest-ever flotilla of tall ships from around the world, all sailing into the Port of New York and New Jersey for a truly majestic nautical spectacle.
$3,218 Per Person
This trip is currently waitlisted, please call to be added to the list.
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A world-class maritime celebration in one of America's finest ports.
After our trip to NYC for Sail4th, the American Eagle will be joining the party as it heads north to SailBoston. This unforgettable experience will showcase tall ships from all over the world, all convening in Boston Harbor. What's better than a front row seat to a generational spectacle like this?
$2,822 Per Person
This trip is currently waitlisted, please call to be added to the waitlist.
July
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Enjoy the quiet anchorages and beautiful bays we call home.
A 4-night adventure that will take you through our favorite islands across Penobscot Bay. Enjoy delicious food, coastal villages, and deserted island exploration on this trip.
$1,466 Per Person
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Six nights, no itinerary; where can we go?
A classic Maine Windjamming adventure, 6-nights to explore Penobscot Bay and beyond. Let's see what we can see and where we can go! Perhaps a visit to the iconic Mt. Desert Island and the stunning Valley Cove, or perhaps a visit to the spruce-studded Isle au Haut. All we know is that it will be aboard the Schooner American Eagle, complete with good company and even better cooking.
$1,781 Per Person
August
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Booked for a private charter.
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Book for a private charter.
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Darlin' Corey joins us for another musical trip during the height of the Perseid Meteor Showers.
Enjoy the peak of Maine summer set to the soundtrack of folk duo Darlin’ Corey. Sit on the deck, gazing up at the clear skies, hunting for meteors in the evening while exploring Penobscot Bay during the day.
$1,633 Per Person
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Explore the hundreds of islands and villages our cruising grounds have to offer.
Your last chance to explore more of what the thousands of islands in our cruising ground have to offer for the 2025 season. Let's go hiking! Just like all of our trips, choose your own adventure, as hiking is anywhere from a stroll to a bit of rock scrambling with water views in every corner! If hiking isn't quite to your taste, it is a nice time to relax on the many pocket beaches, wade in the tidepools, and take in all the surroundings.
$1,466 Per Person
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From spruce-covered islands to fishing villages, a taste of the best of Maine.
Don't work your summer away! This trip is the perfect weekend sailing adventure before the summer is behind us. The best introduction to windjamming! Enjoy delicious scratch cooking, soak up the sun on deck, and marvel at the iconic Maine coastline as we sail through Penobscot Bay.
$1,308 Per Person
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Enjoy the quiet anchorages and beautiful bays we call home.
A 4-night adventure that will take you through our favorite islands across Penobscot Bay. Enjoy delicious food, coastal villages, and deserted island exploration on this trip.
$1,466 Per Person
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The best opportunity to experience Coastal Maine in so little time!
Don't work your summer away! This trip is the perfect weekend sailing adventure before the summer is behind us. The best introduction to windjamming! Enjoy delicious scratch cooking, soak up the sun on deck, and marvel at the iconic Maine coastline as we sail through Penobscot Bay.
$1,308 Per Person
September & October
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From spruce-covered islands to fishing villages, a taste of the best of Maine.
Come enjoy the quiet anchorages and beautiful bays we call home, the perfect mix of sailing and shoreside exploring. The perfect addition to any Maine vacation.
$1,048 Per Person
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The final WIndjammer fleet meet-up of the year!
WoodenBoat Magazine of Brooklin, Maine, is our gracious host for our final Windjammer fleet get together. 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. Don’t miss the last chance to see all the boats in one place!
$1,657 Per Person
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Cooler days and cozy nights are upon us with Drank the Gold & Max Carmichael!
Cooler days and cozy nights are upon us as fall rolls in for the season. This trip pairs the simplicity of acoustic folk music with our favorite pastime, sailing! Join us for one of our last music cruises of the season.
$1,302 Per Person
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The best opportunity to experience coastal Maine in so little time.
A perfect trip for a short adventure on the water. Come see the foliage change from its 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.
$1,048 Per Person
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Combining the two best things about fall: sailing & pie!
Cozy up in the galley for a fall trip all about baking and sailing. It's the perfect time of year to see the foliage change from the very best view, the coast of Maine! All the while learning some pie FUN-damentals. From how to make the perfect crust, getting your fillings just right, crimping, and how to take the perfect pie photo. You'll receive not just tips but a goodie bag full of items to make holiday baking a breeze when you return to shore.
The trip will include all your favorite fall eatings paired with island exploration while warming up alongside our wood stove with pie in hand. Fall sailing is unlike any other and definitely worth having to pack the warmer layers up in the galley for a fall trip, all about baking and sailing
Come see the foliage change from the very best view, the coast of Maine! All your favorite fall eats paired with island exploration while warming up alongside our woodstove. Fall sailing is unlike any other and definitely worth having to pack the warmer layers.
$1,240 Per Person
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Thank you all for another phenomenal season!
Come join us for one last turn around the bay before we put the Eagle to bed for the winter months. Reese Fulmer will be joining us to send off our 2026 sailing season in style!
$1,143 Per Person
Booking and Cancellation Policy
All our cabins accommodate two; Cabins F and G can be guaranteed as single occupancy for an additional $60 per night. Upper and Lower Cabins can be booked privately for single occupancy or shared at the per-person rate. 35% of your trip cost is due at the time of booking, with the balance due 8 weeks before the trip date. A full refund, less a $50 per person fee, will be provided until the balance-due date. Should you cancel with less than 8 weeks’ notice, your payment, less the $50 fee, will be refunded only if a new guest books in place of your cancellation. Re-bookings are subject to a $50 per-person fee. Prices listed do not include online booking provider costs. All bookings are subject to change at any time.
Payment Methods
Payments may be made by check, Visa, MasterCard, Discover, or American Express.