2027 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 2027 schedule here.
May & June
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Sit back and relax as the captain and crew show you their favorite spots after a long winter away.
Spend Memorial Day Weekend with us as we finally put down our paint brushes and set our sails for the first trip of the 2027 sailing season.
$1,395 Per Person | Book Here
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Early-season sailing is perfect if you are looking for a strong sailing breeze and want to experience Maine before the summer crowds come to town.
Our "Island & Villages" trips are perfect if you are looking for the perfect balance of sailing and exploring. We'll go ashore to venture into one of the hundreds of islands the Midcoast area has to offer, or stop into one of the small fishing villages as we sail from anchorage to anchorage.
$1,395 Per Person | Book Here
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One of our most popular trips each season, Reese Fulmer and the Carriage House Band will join us again!
The four-piece band will leave you humming and tapping along with their modern folk music. Informal sets will be played throughout the trip, with the fan-favorite performance during the Schooner Gam. The Schooner Gam is the first fleet gathering of the Maine Windjammer Association of the year. On one of the evenings during the trip, all nine vessels will spend a night (weather permitting) rafted together. Guests of all the boats get the chance to boat hop from deck to deck and participate in the largest raft-up of traditional tall ships on the East Coast.
$1,910 Per Person | Book Here
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The first true weekend escape of the season!
Join us as we take advantage of the longest days of the year and sail as late as the light will let us. This trip is perfect if you are looking for a getaway to relax, rest, and recharge. As the first taste of summer, we'll bring you to our favorite anchorages and see as many sights as we can.
$1,223 Per Person | Book Here
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The perfect getaway over the longest days of the year!
Our "Bays & Islands" trips are offered as our more sailing-centric voyages. Over the course of the trip, we will make the most of our days and go where the wind and the tides take us. With fewer stops ashore combined with some of the longest days of the year, it leaves plenty of time for us to haul up our anchor and discover a new favorite harbor.
$1,395 Per Person | Book Here
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Early-season sailing is perfect if you are looking for a strong sailing breeze and want to experience Maine before the summer crowds come to town.
Our "Island & Villages" trips are perfect if you are looking for the perfect balance of sailing and exploring. We'll go ashore to venture into one of the hundreds of islands the Midcoast area has to offer, or stop into one of the small fishing villages as we sail from anchorage to anchorage.
$1,395 Per Person | Book Here
July
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Take part in one of the largest traditional races of schooners in North America!
Get your competitive edge on and join us as we participate in the 47th Annual Great Schooner Race. As a part of the Windward class, we'll race for the claim over the cup again. The race is the second event of the year for the Maine Windjammer Association, and there is no shortage of competition. Starting the night before the "big boat" race, the crews participate in the small boat race. Watch as our crew fights to defend its title for the fourth year in a row. The following morning, the race course is determined, and each class starts over the line. Cross your fingers for loads of wind; we will not hold back and charge to cross the finish line first.
$2, 048 Per Person | Book Here
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Summer is just getting started!
Get away from the hustle and bustle and join our "Bays & Islands"— our more sailing-centric voyages. Experience Midcoast Maine from this unique point of view as we watch the islands pass by. Over the course of the trip, we will make the most of our days and go where the wind and the tides take us. With fewer stops ashore, combined with some of the most optimal weather of the year, it leaves plenty of time for us to haul up our anchor and discover a new favorite harbor.
$1,591 Per Person | Book Here
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Make the most of the weekend and experience Maine in so little time.
A perfect trip for a short adventure on the water. Enjoy two days of sailing and exploring Penobscot Bay as you sit back and relax. All-inclusive means that you can leave all of the planning and decision-making to us. This trip is the best introduction to windjamming!
$1,505 Per Person | Book Here
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Experience peak summer weather in Maine... from the water!
Five nights give us plenty of time to explore some of our favorite bays in the area. Come with us as we follow the shorelines of spruce-studded islands and anchor by quaint fishing villages. Paired with our farm-to-table creations coming out of the galley, this is a true windjamming trip with no set itinerary.
$1,934 Per Person | Book Here
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Make the most of your time in Maine!
Join us on a traditional windjamming trip as we explore the islands in the Midcoast area. Either come up just for the occasion as a mid-summer escape, or add it to either end of your Maine vacation as you explore the coast. Complete with a lobster bake, you'll get the full New England experience packed into just a few days.
$1,440 Per Person | Book Here
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Enjoy an extended weekend as we cruise into August.
Four nights is the perfect amount of time to get out and go sightseeing in our backyard. Our "Island & Villages" trips are ideal if you are looking for the perfect balance of sailing and exploring. We'll go ashore to venture into one of the hundreds of islands the Midcoast area has to offer, or stop into one of the small fishing villages as we sail from anchorage to anchorage.
$1,686 Per Person | Book Here
August
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Sail into the weekend!
Escape the summer crowds and join our "Bays & Islands"— our more sailing-centric voyage. Experience Midcoast Maine from this unique point of view as we watch the islands pass by. Over the course of the trip, we will make the most of our days and go where the wind and the tides take us. With fewer stops ashore, combined with some of the most optimal weather of the year, it leaves plenty of time for us to haul up our anchor and discover a new favorite harbor.
$1,686 Per Person | Book Here
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Experience peak summer weather in Maine... from the water!
Five nights give us plenty of time to explore some of our favorite bays in the area. Come with us as we follow the shorelines of spruce-studded islands and anchor by quaint fishing villages. Paired with our farm-to-table creations coming out of the galley, this is a true windjamming trip with no set itinerary. Beat the summer crowds and get the full New England experience in Penobscot Bay and beyond.
$1,934 Per Person | Book Here
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Six nights, no itinerary; where can we go?!
We're going back to the basics and setting sail on a classic Maine Windjamming adventure. Six nights give us plenty of time 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. The only thing we have planned for this trip is good cooking and even better company.
$2,048 Per Person | Book Here
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Soak in the summer weather.
Our "Island & Villages" trips are perfect if you are looking for the perfect balance of sailing and exploring. We'll go ashore to venture into one of the hundreds of islands the Midcoast area has to offer, or stop into one of the small fishing villages as we sail from anchorage to anchorage. Complete with a lobster bake, you'll get the full New England experience packed into just a few days.
$1,615 Per Person | Book Here
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Enjoy a weekend on the water as we say goodbye to August.
Three nights is the perfect amount of time to get out and go sightseeing in our backyard. Our "Weekend Escape" trip is the perfect addition to a New England trip. Experience Midcoast Maine from this unique point of view as we watch the islands pass by. Over the course of the trip, we will make the most of our days and go where the wind and the tides take us. With fewer stops ashore, combined with some of the most optimal weather of the year, it leaves plenty of time for us to haul up our anchor and discover a new favorite harbor.
$1,028 Per Person | Book Here
October
September
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Summer isn't over yet!
Make the most of the week and experience Maine in so little time. A perfect trip for a short adventure on the water. Enjoy two days of sailing and exploring Penobscot Bay as you sit back and relax. All-inclusive means that you can leave all of the planning and decision-making to us. This trip is the best introduction to windjamming!
$1,153 Per Person | Book Here
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Join us for the last Maine Windjammer event of the year!
Sail with us as we anchor in Brooklin, Maine, with the whole fleet for one final time in the season. Home of the WoodenBoat School and Magazine, we'll get the chance to be in the presence of legendary vessels. This six-night trip is typically our last chance in the season to get as far Downeast as possible. Watch from the water as the fall foliage starts to turn, the wind starts to pick up again, and nights are kept warm by the wood-burning stove.
$1,740 Per Person | Book Here
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Join us for our Celtic Isles trip!
Cool days and cozy nights are upon us as fall begins to roll in. This trip pairs the simplicity of acoustic folk music with our favorite pastime of sailing. Bring your knit sweater and curl up on deck with a cup of tea, and we'll sail as long as the light will let us.
$1,475 Per Person | Book Here
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Get your sailing fix in while you can!
This three-night is the last weekend sail for the season! Join us as we watch the islands pass by and the leaves on the trees change colors. Over the course of the trip, we will make the most of our days and go where the wind and the tides take us. Either come up just for the occasion as an autumn escape, or add it to either end of your Maine vacation as you explore the coast. Complete with a lobster bake, you'll get the full New England experience packed into just a few days.
$1,153 Per Person | Book Here
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Grab your sweaters and cozy up on the boat, we'll watch and see all the foliage turn from the water!
Our "Island & Villages" trips are perfect if you are looking for the perfect balance of sailing and exploring. We'll go ashore to venture into one of the hundreds of islands the Midcoast area has to offer, or stop into one of the small fishing villages as we sail from anchorage to anchorage. Complete with a lobster bake, you'll get the full New England experience packed into just a few days.
$1,364 Per Person | Book Here
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This trip is the key to visiting Maine during the locals' favorite time of year!
Skip the summer crowd and take a quiet trip where the wood-burning stoves are roaring and nights are filled with stellar stars. The cooler weather makes for great sailing days and spectacular sunsets. Spend nights on deck as we find a dark anchorage to watch the autumnal constellations reach their peak.
$1,153 Per Person | Book Here
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Closing out our 41st windjamming season the only way we know how: sailing!
Make the most of the holiday weekend and come join us for one last turn around the bay before we put American Eagle to bed for the winter months.
$1,364 Per Person | Book Here
Re-Booking and Cancellation Policy
At the time of booking, at least a 35% deposit is due to reserve a cabin(s). If there is a balance remaining, it will be due eight weeks before the trip date.
If you need to cancel your reservation, a full refund, less a $50 per person fee, will be provided until eight weeks before the trip date.
Should you cancel with less than eight weeks’ notice, your payment, less the $50 fee, will be refunded if a new guest books in place of your cancellation.
All re-bookings are subject to a $50 per-person fee and are only applicable for the same sailing season. No refunds will be given if rebooking to a trip of lesser value within eight weeks of the trip. Should you cancel after re-booking a trip, you will not be refunded.
It is strongly recommended to purchase trip insurance through a third party to protect your trip, should you have to cancel or rebook.
Payment Methods
Payments may be made by check, Visa, MasterCard, Discover, or American Express.