We Found These Experiences For You (35)
5 Nights ~ Darlin' Corey Music & Meteor Showers
5 Nights • Tuesday, August 10th - Saturday, August 15th • Starting at $1,633 Per Person
Darker anchorages are our goal for this celestial event. Stay up late or wake up extra early to view to view the Perseids, an annual meteor shower that passes over every summer. Dark anchorages are our goals and clear skies are our wish for this wonderful event. It wouldn't be a windjamming trip ...
Rockland
Monday, August 10th - Saturday, August 15th
Schooner American Eagle
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4 Nights ~ Hiking and Island Exploration
4 Nights • Sunday, August 16th - Thursday, August 20th • Starting at $1,466 Per Person
Explore the hundreds of islands and hidden 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 ...
Rockland
Sunday, August 16th - Thursday, August 20th
Schooner American Eagle
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4 Nights ~ Bays & Islands
4 Nights • Tuesday, August 25th - Saturday, August 29th • Starting at $1,466
Enjoy the quiet anchorages and beautiful bays we call home Come enjoy the quiet anchorages and beautiful bays we call home. A 4-Night trip that will encompass all we love about sailing along the coast of Maine. Boarding and Returning All trips board between 5 - 6 pm on the date listed All trips return ...
Rockland
Tuesday, August 25th - Saturday, August 29th
Schooner American Eagle
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3 Nights ~ Main Sails and Lobster Tails
3 Nights • Sunday, August 30th - Wednesday, September 2nd • Starting at $1,308
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! Enjoy the last of the long summer days. Boarding and Returning All trips board between 5 - 6 pm ...
Rockland
Sunday, August 30th - Wednesday, September 2nd
Schooner American Eagle
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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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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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