Come 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. We also have several specialty cruises throughout the summer: a 9-night trip Downeast to the Canadian Border and a 9-night journey south to Gloucester, Massachusetts. No matter how long you are aboard, you will have no shortage of good food, stunning scenery, memorable moments and great people. 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!
Every trip is available for charter until the first person reserves.
Download our 2025 schedule
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| Board 5-6 pm |
Return by 11 am |
# of Nights | Description | Rate per person | |
|---|---|---|---|---|---|
| Friday, May 30 | Monday, June 2 | 3 | Spring Sailing – 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, be the first to see Penobscot Bay and the schooner welcome in summer. | $998 | |
| Thursday, June 5 | Sunday, June 8 | 3 | Early Summer Sailing – Enjoy the sailing weather as the change of seasons brings a good strong breeze. Explore quiet anchorages before the summer season is in full swing. | $998 | |
| Monday, June 9 | Saturday, June 14 | 5 | Reese Fulmer and the Carriage House Band – Schooner Gam – Join us on this 5-night adventure with modern folk group: Reese Fulmer and the Carriage House Band. One evening we’ll raft up with the entire Windjammer fleet for an evening together. | $1,311 | |
| Sunday, June 15 | Thursday, June 19 | 4 | Bays and Islands – Enjoy the quiet anchorages and beautiful bays we call home–the perfect mix of sailing and shoreside exploring. | $1,208 | |
| Friday, June 20 | Tuesday, June 24 | 4 | Summer Solstice – A perfect sailing getaway over the longest days of the year–plenty of daylight to explore Penobscot Bay on an original Gloucester Fishing Schooner. | $1,208 | |
| Wednesday, June 25 | Saturday, June 28 | 3 | Main Sails and Lobster Tails – The perfect opportunity to experience Coastal Maine in so little time! Two days of sailing and a quintessential lobster bake on a quiet beach; what could be better? | $1,058 | |
| Sunday, June 29 | Saturday, July 5 | 6 | Great Schooner Race – Booked for private charter | $1,736 | |
| Sunday, July 6 | Thursday, July 10 | 4 | Coastline Classics – A simple short getaway: two days of sailing and time to explore a coastal village or deserted island, all on a beautiful Gloucester Fishing Schooner. | $1,396 | |
| Friday, July 11 | Tuesday, July 15 | 4 | Hiking and Island Exploration – Explore hundreds of islands or villages. Hiking ranges from easy strolls to rock scrambling with water views. If hiking isn’t your thing, lounge on beaches, wade in tidepools, and take in the stunning surroundings. | $1,396 | |
| Thursday, July 17 | Tuesday, July 22 | 5 | Eastbound: Blue Hill Bay and Beyond – A chance to go beyond our normal cruising grounds, visiting anchorages a bit farther from home. | $1,546 | |
| Wednesday, July 23 | Saturday, July 26 | 3 | Main Sails and Lobster Tails – Two days of sailing with a lobster bake on a quiet beach; a perfect mini-getaway. | $1,246 | |
| Friday, July 27 | Saturday, August 2 | 6 | Unscripted Adventure – A classic Maine Windjamming adventure: six nights and no set itinerary. Let’s see where we go—Isle la Haut? Mt. Desert Island? Who knows! | $1,696 | |
| Sunday, August 3 | Thursday, August 7 | 4 | Hiking and Island Exploration – The perfect trip to explore the hundreds of islands and villages our cruising grounds have to offer. Hiking is anything from an easy stroll to a bit of rock scrambling with water views around every corner! If hiking is not quite to your taste lounge on the many pocket beaches, wade in the tide pools, or takin in the beautiful surroundings. | $1,396 | |
| Friday, August 8 | Monday, August 11 | 3 | Persied Meteor Showers – Darker anchorages are our aim this week for a chance to see this annual celestial event. | $1,246 | |
| Tuesday, August 12 | Saturday, August 16 | 4 | Booked for Private Charter | $1,396 |
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| Sunday, August 17 | Thursday, August 21 | 4 | Hiking and Island Exploration – The perfect trip to explore the hundreds of islands and villages our cruising grounds have to offer. Hiking is anything from an easy stroll to a bit of rock scrambling with water views around every corner! If hiking is not quite to your taste lounge on the many pocket beaches, wade in the tide pools, or takin in the beautiful surroundings. | $1,396 | |
| Friday, August 22 | Monday, August 25 | 3 | Coastal Classics – From spruce covered islands to fishing villages with stunning views all around there is much to fill each moment. A fraction of the cost of chartering your own vessel! | $1,246 | |
| Wednesday, August 27 | Thursday, September 4 | 9 | Gloucester Schooner Race – Our annual trip home for both the Eagle and Capt. King. A long haul adventure along a classic portion of the east coast. See visiting schooners and experiance over 400 years of history of America’s oldest fishing port from the deck of one of its last surviving fishing schooners. All culminating in our chance to win the Esperanto Cup once again! | $2,506 | |
| Sunday, September 7 | Saturday, September 13 | 6 | Woodenboat Sail-In – Woodenboat Magazine is our gracious host for the final Windjammer fleet get together, with a gathering for an evening on their stunning grounds with the anchorage full of beautiful windjammers is such a fine way to send off the season in style. | $1,578 | |
| Sunday, September 14 | Friday, September 19 | 5 | Fall Eastbound – Booked for private Charter. | ||
| Sunday, September 21 | Thursday, September 25 | 4 | Celtic Isles -Join us for a misty sojourn through the isles of Penobscot Bay. Watch the fall foliage begin to change during the day and cozy up in our wood-paneled galley in the evening. | $1,128 | |
| Friday, September 26 | Tuesday, September 30th | 4 | Autumn on the Bay -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 of warmth aboard. Fall sailing in Maine is stunning. | $1,128 | |
| Thursday, October 2 | Sunday, October 5 | 3 | One Last Turn Around the Bay-Thank you all for another phenominal season! Come join us for one last turn around the bay before we put the Eagle to bed for the winter we’ll dry our sails and have one more chance to visit a couple of our favorite anchorages. | $998 |
Full Moon
& = unique to Schooner American Eagle
The Maine coast is waiting for you…
Booking and Cancellation Policy
All our cabins accommodate two; Cabins A and B can be guaranteed as single occupancy for an additional $30 per night. 35% of your trip cost is due at the time of booking with the balance due 6 weeks before the trip date. A full refund, less $50 per person fee, will be provided until the balance-due date. Should you cancel with less than six weeks’ notice, your payment less the $50 fee will be refunded if a new guest books in place of your cancellation. Re-bookings are subject to a $50 per-person fee.
Payment Methods
Payments may be made by check, VISA, MasterCard, DISCOVER or American Express.
Request a brochure and schedule
Visit our Contact Us page to request a paper brochure and schedule by mail.
