We Found These Experiences For You (28)
Schooner American Eagle
3 Nights ~ Coastal Classics
3 Nights • Wednesday, September 9th - Saturday, September 12th • Starting at $1,048
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. Join us for two days of wonderful food, island exploring, and sailing throughout Penobscot Bay. Boarding ...
Rockland
Wednesday, September 9th - Saturday, September 1
Schooner American Eagle
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6 Nights ~ Wooden Boat Sail-In
6 Nights • Sunday, September 13th - Saturday, September 19th • Starting at $1,657 per person
Join us for the final Windjammer meetup of the season Wooden Boat Magazine 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. Boarding and ...
Rockland
Sunday, September 13th - Saturday, September 19t
Schooner American Eagle
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4 Nights ~ Celtic Isles
4 Nights • Sunday, September 20th - Thursday, September 24th • Starting at $1,302
Cooler days and cozy nights are upon us Drank the Gold joins us for a misty sojourn through the isles of Penobscot Bay. Watch the foliage begin to change during the day and in the evening cozy up in our wood-paneled galley to a concert of Celtic melodies. Boarding and Returning All trips board between ...
Rockland
Sunday, September 20th - Thursday, September 24t
Schooner American Eagle
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3 Nights ~ Main Sails and Lobster Tails
3 Nights • Friday, September 25th - Monday, September 28th • Starting at $1,048
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 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 ...
Rockland
Friday, September 25th - Monday, September 28th
Schooner American Eagle
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3 Nights ~ One Last Turn Around the Bay
3 Nights • Monday, October 5th - Thursday, October 8th • Starting at $1,143 per person
One last turn around the bay for 2026! Thank you all for a phenomenal season come join us for one last turn around the bay before we put the Eagle to bed for the winter months. Boarding and Returning All trips board between 5 - 6 pm on the date listed All trips return by 10am of the last date listed ...
Rockland
Monday, October 5th - Thursday, October 8th
Schooner American Eagle
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Spring Sailing ~ 4 Nights ~ 2027
4 Nights • Thursday, May 27th- Monday, May 31st • Starting at $349 Per-Person Per Day
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. Sit back and relax as the captain and crew show you their favorite spots after a long winter away. Our Vessel Built in 1930, the Schooner American Eagle measures ...
Rockland
Thursday, May 27th - Monday, May 31st
Schooner American Eagle
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Islands & Villages ~ 4 Nights ~ 2027
4 Nights • Monday, June 7th- Friday, June 11th • Starting at $349 Per-Person Per Day
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 ...
Rockland
Monday, June 7th- Friday, June 11th
Schooner American Eagle
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Gathering of the Fleet ~ 5 Nights ~ 2027
5 Nights • Saturday, June 12th- Thursday, June 17th • Starting at $382 Per-Person Per Day
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. ...
Rockland
Saturday, June 12th- Thursday, June 17th
Schooner American Eagle
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Weekend Escape ~ 3 Nights ~ 2027
3 Nights • Friday, June 18th- Monday, June 21st • Starting at $408 Per-Person Per Day
The first true weekend escape of the year. 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 ...
Rockland
Friday, June 18th- Monday, June 21st
Schooner American Eagle
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Bays & Islands ~ 4 Nights ~ 2027
4 Nights • Tuesday, June 22nd- Saturday, June 26th • Starting at $349 Per-Person Per Day
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 ...
Rockland
Tuesday, June 22nd- Saturday, June 26th
Schooner American Eagle
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Islands & Villages ~ 4 Nights ~ 2027
4 Nights • Sunday, June 27th- Thursday, July 1st • Starting at $349 Per-Person Per Day
Early-season sailing is perfect if you are looking for a strong 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 ...
Rockland
Sunday, June 27th- Thursday, July 1st
Schooner American Eagle
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Great Schooner Race Week ~ 6 Nights ~ 2027
6 Nights • Sunday, July 4th- Saturday, July 10th • Starting at $341 Per-Person Per Day
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 ...
Rockland
Sunday, July 4th- Saturday, July 10th
Schooner American Eagle
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Bays & Islands ~ 4 Nights ~ 2027
4 Nights • Sunday, July 11th- Thursday, July 15th • Starting at $398 Per-Person Per Day
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 ...
Rockland
Sunday, July 11th- Thursday, July 15th
Schooner American Eagle
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Weekend Escape ~ 3 Nights - 2027
3 Nights • Friday, July 16th- Monday, July 19th • Starting at $502 Per-Person Per Day
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 ...
Rockland
Friday, July 16th- Monday, July 19th
Schooner American Eagle
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Coastal Classics ~ 5 Nights ~ 2027
5 Nights • Tuesday, July 20th- Sunday, July 25th • Starting at $387 Per-Person Per Day
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 ...
Rockland
Tuesday, July 20th- Sunday, July 25th
Schooner American Eagle
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Early Week Escape ~ 3 Nights ~ 2027
3 Nights • Monday, July 26th- Thursday, July 29th • Starting at $480 Per-Person Per Day
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 ...
Rockland
Monday, July 26th- Thursday, July 29th
Schooner American Eagle
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Islands & Villages ~ 4 Nights ~ 2027
4 Nights • Friday, July 30th- Tuesday, August 3rd • Starting at $422 Per-Person Per Day
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 ...
Rockland
Friday, July 30th- Tuesday, August 3rd
Schooner American Eagle
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Bays & Islands ~ 4 Nights ~ 2027
4 Nights • Wednesday, August 4th- Sunday, August 8th • Starting at $422 Per-Person Per Day
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 ...
Rockland
Wednesday, August 4th- Sunday, August 8th
Schooner American Eagle
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Coastal Classics ~ 5 Nights ~ 2027
5 Nights • Monday, August 9th- Saturday, August 14th • Starting at $387 Per-Person Per Day
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 ...
Rockland
Monday, August 9th- Saturday, August 14th
Schooner American Eagle
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Unscripted Adventure ~ 6 Nights ~ 2027
6 Nights • Sunday, August 15th- Saturday, August 21st • Starting at $341 Per-Person Per Day
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 ...
Rockland
Sunday, August 15th- Saturday, August 21st
Schooner American Eagle
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Viewing 1 to 20 of 28 Experiences