We Found These Experiences For You (19)
3 Nights - Spring Sailing
3 Nights • Friday, May 29th - Monday, June 1st • Starting at $1,048 Per Person
Put those paintbrushes down, we're going sailing! The first trip of the season! Come aboard and let's get everything in full swing. Be the first to stay onboard for the season and say hello to Penobscot Bay for the summer to come. More info Accommodates 26 guests; 92 feet on deck All upper ...
Rockland
Friday, May 29th - Monday, June 1st
Schooner American Eagle
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3 Nights ~ Early Summer Sailing
3 Nights • Wednesday, June 3rd - Saturday, June 6th • Starting at $1,048 Per Person
Welcome in the summer! Early season sailing is a time for good strong breezes, long days, and vibrant skies as we welcome the summer weather into our season. Join us for second trip of 2026, with farm to table creations, wonderful company along the coast of Maine. Includes All meals (excluding dinner ...
Rockland
Wednesday, June 3rd - Saturday, June 6th
Schooner American Eagle
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5 Nights ~ Reese Fulmer and the Carriage House Band - Schooner Gam
5 Nights • Sunday, June 7th - Friday, June 12th • Starting at $1,514 Per Person
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 ...
Sunday, June 7th - Friday, June 12th
Schooner American Eagle
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3 Nights ~ Coastal Classics
3 Nights • Sunday, June 14th - Wednesday, June 17th • Starting at $1,111
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. Boarding and Returning All trips board between 5 - 6 pm on the ...
Rockland
Sunday, June 14th - Wednesday, June 17th
Schooner American Eagle
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4 Nights ~ Summer Solstice
4 Nights • Thursday, June 18th - Monday, June 22nd • Starting at $1,268
The perfect getaway over the longest days of the year A simple cruise over the longest days of sailing we have all year. Enjoy 4-nights on our beloved Gloucester Fishing Schooner while having a little more daylight to explore a coastal village or deserted island along Maine's shoreline. Boarding ...
Rockland
Thursday, June 18th - Monday, June 22nd
Schooner American Eagle
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3 Nights ~ Main Sails and Lobster Tails
3 Nights • Tuesday, June 23rd - Friday, June 26th • Starting at $1,111 Per Person
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! Boarding and Returning All trips board between 5 - 6 pm on the date listed All trips return by 11am ...
Rockland
Tuesday, June 23rd - Friday, June 26th
Schooner American Eagle
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4 Nights ~ Bays & Islands
4 Nights • Tuesday, July 21st - Saturday, July 25th • Starting at $1,466 per person
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. Boarding and Returning All trips board between 5 - 6 pm on the date ...
Rockland
Tuesday, July 21st - Saturday, July 25th
Schooner American Eagle
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6 Nights ~ Unscripted Adventure
6 Nights • Sunday, July 26th - Saturday, August 1st • Starting at $1,781 per person
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. Dessert Island and the stunning Valley Cove, or perhaps a visit to the spruce-studded Isle ...
Rockland
Sunday, July 26th - Saturday, August 1st
Schooner American Eagle
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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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3 Nights ~ Coastal Classics
3 Nights • Friday, August 21st - Monday, August 24th • Starting at $1,308
Catch one of the last weekends of summer! 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 ...
Rockland
Friday, August 21st - Monday, August 24th
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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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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4 Nights ~ Autumn Desserts with Stacey Mei Yan Fong
4 Nights • Wednesday, September 30th - Sunday, October 4th • Starting at $1,240 per person
See the foliage change from the very best view Come see the foliage change from the very best view, the coast of Maine! All your favorite fall eatings paired with island exploration while warming up along side our woodstove. Fall sailing is unlike no other and definitely worth having to pack the warmer ...
Rockland
Wednesday, September 30th - Sunday, October 4th
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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