We hope you’ll join us for the 2022 season. We have a nice variety of 3- to 6-night trips, as well as a couple of longer adventures: a 7-night trip Downeast and a 9-night to Gloucester, Massachusetts. Take a look at the schedule below and then give us a call to check the availability on the trip that works with your calendar.
5% discount for those having sailed with us before. Every trip is available for charter until the first person reserves.
Download Our 2022 Schedule
| Board 5-6 pm |
Return by 11 am |
# of Nights | Description | Rate per person | |
|---|---|---|---|---|---|
| * Friday May 27 |
Monday May 30 |
3 | SHAKEDOWN SAIL | $745 | Book |
| Wednesday June 1 |
Sunday June 5 |
4 | CLEAR SAILING INTO SUMMER | $850 | Book |
| & Monday June 6 |
Saturday June 11 |
5 | HIDDEN TRACES OF THE PAST– A guided look into the little-known history of Penobscot Bay. | $995 | Book |
| Sunday June 12  |
Thursday June 16 |
4 | SCHOONER GAM – First of our annual windjammer fleet events. One afternoon we’ll all head for the same harbor for an evening together. | $850 | Book |
| Friday June 17 |
Monday June 20 |
3 | LONG DAYS FOR A WEEKEND JAUNT | $795 | Book |
| & Tuesday June 21 |
Saturday June 25 |
4 | SUMMER SOLSTICE & WATERCOLOR WORKSHOP – Spend the longest of evenings capturing the colors of summer. Artist Carol L. Douglas will join us to lead a plein air watercolor workshop aboard. (Additional $395 charge if you wish to participate in the workshop. Supplies provided.) | $925 | Book |
| * Sunday June 26 |
Saturday July 2 |
6 | WINDJAMMER DAYS TO BOOTHBAY HARBOR – Sail into exciting Booth Bay with a lobster bake and fireworks. We often see puffins and sometimes even whales on our way. | $1,230 | Book |
| Sunday July 3 |
Saturday July 9 |
6 | 4th OF JULY/ GREAT SCHOONER RACE Another chance to see the windjammer fleet and visiting vessels converge for our annual race. With a small boat race the evening before, the laughter and camaraderie never stop. | $1,275 | Book |
| & Sunday July 10 |
Thursday July 14 |
4 | CASTLEBAY~ Enjoy the music of Maine and the Celtic isles of Scotland and Ireland performed by Julia Lane and Fred Gosbee of Castlebay. Informal talks throughout the days and evenings. Bring your voice, and your musical instrument, if you so choose! | $1,075 | Book |
| Friday July 15 |
Monday July 18 |
3 | WEEKEND MID-SUMMER ADVENTURE – An incredible short getaway | $880 | Book |
| Tuesday July 19 |
Saturday July 23 |
4 | TRADITIONAL COASTAL SAILING – Come see what windjamming is all about. | $975 | Book |
| * & Sunday July 24 |
Sunday July 31 |
7 | DOWNEAST TRIP – A chance to go farther downeast beyond our normal cruising grounds where bold landscapes and nature prevail. | $1,595 | Book |
| Monday Aug 1 |
Saturday Aug 6 |
5 | SWAN’S ISLAND MUSIC FESTIVAL – Five days of sailing with a lobster feast and an evening of eclectic music at the Sweet Chariot Music Festival. | $1,195 | Book |
| Sunday Aug 7 |
Wednesday Aug 10 |
3 | MID-SUMMER ADVENTURE – An incredible short getaway with an chance to perhaps see a meteor shower. | $880 | Book |
| Thursday Aug 11 |
Monday Aug 15 |
4 | HIKING & ISLAND EXPLORATION- Explore more of what the islands in our cruising ground offer. Hiking can be anywhere from a stroll to a bit of rock scrambling with water views in every corner! If hiking isn’t quite to your taste, it’s a nice time to relax on the many pocket beaches. | $975 | Book |
| Tuesday Aug 16 |
Friday Aug 19 |
3 | PERSIED METEOR SHOWERS – If the nights are dark enough, we’ll be able to see this famed annual event. | $880 | Book |
| Saturday Aug 20 |
Thursday Aug 25 |
5 | HIGH SUMMER HIKING & ISLAND EXPLORATION -Another hiking trip with an extra day to explore, giving us even more time to get to places that are farther away. | $1,195 | Book |
| Friday Aug 26 |
Tuesday Aug 30 |
4 | TRADITIONAL COASTAL SAILING – Come see what windjamming is all about. | $975 | Book |
| * & Wednesday Aug 31 |
Friday Sept 9 |
9 | GLOUCESTER SCHOONER RACE – Our annual trip home, for both the EAGLE and Capt. King. A long adventure, “Homeward Bound” to America’s oldest fishing port, allows for sailing offshore along a beautiful portion of the east coast with a good chance to see whales and other marine wildlife on our way to race for the Esperanto Cup once again. | $1,995 | Book |
| Sunday Sept 11 |
Saturday Sept 17 |
6 | WOODENBOAT SAIL-IN – Our final windjammer fleet get-together. We all meet in WoodenBoat Harbor for an evening of music, refreshments, and small boat activities. | $1,230 | Book |
| & Sunday Sept 18 |
Thursday Sept 22 |
4 | FALL COLORS & WATERCOLOR WORKSHOP – Changing foliage contrasted with dark evergreens and the blues of the bay offer breathtaking panoramas. Artists of all levels are welcomed to join Carol Douglas’s workshop. (Additional $395 charge for the workshop. Supplies provided.) | $895 | Book |
| Friday Sept 23 |
Monday Sept 26 |
3 | AUTUMN WEEKEND – Come see the foliage change from the most striking side, the ocean! | $760 | Book |
| Tuesday Sept 27 |
Saturday Oct 1 |
4 | COOL DAYS AND COZY NIGHTS – A time to watch the quiet change of a landscape through yet another season. | $895 | Book |
| Sunday Oct 2 |
Thursday Oct 6 |
4 | FALL FOLIAGE IN FULL SWING – Crisp breezes make this an incredible time for a lively sail | $895 | Book |
| * Friday Oct 7 |
Wednesday Oct 12 |
5 | THAT’S IT FOR 2022! – Join us for our last hurrah of 2022. Now here’s to 2023! | $975 | Book |
Full Moon Any trip over a full moon offers us the opportunity for an evening sail.
* = Capt. John Foss will join us for this trip
& = unique to Schooner American Eagle
We hope you can find just the trip to fit your schedule. Please call or email with any questions. We cannot wait to go sailing!
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 until the balance due date. Should you cancel with less than six weeks’ notice, your payment less the $50 fee will be returned only as others are booked for that same trip. Re-bookings are subject to a $50 per person fee.
Payment Methods
Payments may be made by check, VISA, MasterCard or DISCOVER.
Request a brochure and schedule
Head over to our Contact Us page to request a brochure and schedule by mail.
If we don’t have a trip that fits your schedule, we recommend the schooner Heritage also sailing from the North End Shipyard in Rockland.
