Come aboard for our 2023 season and 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: an 8-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!
5% discount on 2023 reservations until February 1st.
Every trip is available for charter until the first person reserves.
Click Here to Download Our 2023 Schedule
| Board 5-6 pm |
Return by 11 am |
# of Nights | Description | Rate per person | |
|---|---|---|---|---|---|
| Friday May 26 |
Monday May 29 |
3 | HOLIDAY WEEKEND – Kick off the season with a weekend adventure! | $875 | Book |
| Tuesday May 30 |
Saturday June 3 |
4 | CLEAR SAILING – Sail wherever the wind takes us! Ideal for a full-boat charter. | $975 | Book |
| Sunday June 4 |
Thursday June 8 |
4 | SPRING SAILING – See the lupines in bloom as we sail into June. | $975 | Book |
| Saturday June 10  |
Thursday June 15 |
5 | WINDJAMMER FLEET RAFT-UP – Our first windjammer fleet event of the season with very special guests Reese Fulmer and the Carriage House Band. Welcome the new season with us — an unforgettable trip filled with good music, good friends and a unique chance to see the whole windjammer fleet rafted up together. | $1,150 | Book |
| Friday June 16 |
Monday June 19 |
3 | FATHER’S DAY WEEKEND – Summer is almost here! Celebrate Father’s Day out on the Bay. | $925 | Book |
| & Tuesday June 20 |
Saturday June 24 |
4 | SUMMER SOLSTICE & WATERCOLOR WORKSHOP – Welcome summer with idyllic sailing, beautiful village walks, and calm rows around quiet harbors. Nationally known artist Carol L. Douglas joins us once again as the host of our watercolor workshop.
*Additional charge if you wish to take part in the workshop. Check out www.watch-me-paint.com! |
$1,065 | Book |
| & Sunday June 25 |
Saturday July 1 |
6 | TRACES OF THE PAST – Come aboard as we journey through the little-known history of Penobscot Bay. With historian Sam Collins as our guide, learn about mid-coast Maine’s industrial and ancient past. | $1,475 | Book |
| Sunday July 2 |
Saturday July 8 |
6 | PHOTOGRAPHY & JULY 4TH RACE – Celebrate Independence Day aboard a National Historic Landmark. Rockland-based photographers Sean & Tracy Sheppard coach you as you capture Maine’s beauty on camera. End the week with a fleet gathering Thursday evening for the annual Great Schooner Race on Friday. No sailing or racing experience needed! | $1,495 | Book |
| Sunday July 9 |
Wednesday July 12 |
3 | THREE NIGHTS ON THE BAY –A couple of days of sailing. No itinerary, no worries. You’ll be more relaxed upon your return than you ever thought possible. | $1,015 | Book |
| Thursday July 13 |
Monday July 17 |
4 | HIKING & ISLAND EXPLORATION – Explore more of what the hundreds of islands throughout our sailing grounds have to offer. Hiking ranges from a stroll to a bit of rock scrambling with water views around every corner! Not a hiker? Take that time to relax on the many secluded beaches we’ll visit. | $1,195 | Book |
| * & Tuesday July 18 |
Wednesday July 26 |
8 | DOWNEAST TRIP – As close to Canada as you can get without needing a passport! Dramatic coastlines beckon us northward across waters less traveled. | $2,095 | Book |
| Friday July 28 |
Monday July 31 |
3 | WEEKEND ESCAPE – What better way to recharge than with a few days of not checking emails, texts, or even the time. Kick back and relax. | $1,015 | Book |
| Tuesday Aug 1 |
Saturday Aug 5 |
4 | SWEET CHARIOT MUSIC FESTIVAL – Join us for an evening of eclectic music in a secluded village on Swan’s Island– accessible only from the water– followed by two more days of summer winds and a lobster feast! | $1,195 | Book |
| Sunday Aug 6 |
Thursday Aug 10 |
4 | CATCH THE COASTLINE – Looking to make the most of your Mainecation? Come aboard for delightful sailing and delicious food. | $1,100 | Book |
| Friday Aug 11 |
Monday Aug 14 |
3 | PERSEID METEOR SHOWERS – Far from the city lights, enjoy this famed celestial event. | $1,015 | Book |
| Tuesday Aug 15 |
Sunday Aug 20 |
5 | HIKING & ISLAND EXPLORATION – With an extra day, we’ll have even more time to explore. | $1,375 | Book |
| & Monday Aug 21 |
Thursday Aug 24 |
3 | MUSIC AMONG THE ISLANDS – Come aboard and experience the music of Darlin’ Corey, a A North American folk music duo from Portland, Maine. Together, Erica Brown and Matt Shipman create elegant harmonies in their original songs and through the traditional Bluegrass, Old Time, and Franco-American tunes that they showcase. Click on the link to listen! https://www.darlincorey.com | $1,115 | Book |
| Friday Aug 25 |
Tuesday Aug 29 |
4 | HIKING & ISLAND EXPLORATION – As we look to the weather, wind, and tide, the final hiking trip of the season provides a flexible island-hopping itinerary. | $1,195 | Book |
| & Wednesday Aug 30 |
Friday Sept 8 |
9 | GLOUCESTER SCHOONER RACE – Our annual trip “Homeward Bound” for both the Eagle and Capt. King. We sail to America’s oldest fishing port as it celebrates its 400th Anniversary. Sailing offshore grants us a chance of seeing whales and other marine wildlife on our way to race for the Esperanto Cup once more. | $2,295 | Book |
| Sunday Sept 10 |
Friday Sept 15 |
5 | WOODENBOAT SAIL-IN – The final windjammer fleet get-together with a midweek rendezvous in WoodenBoat Harbor. Music and activities highlight that evening. | $1,415 | Book |
| & Saturday Sept 16 |
Wednesday Sept 20 |
4 | FALL FOLIAGE & WATERCOLOR WORKSHOP – Changing foliage glows against the dark evergreen trees and the deep blues of the bay. Artists of all levels are welcomed to join in our autumn watercolor workshop of the season, hosted by Carol L. Douglas.
*Additional charge if you wish to take part in the workshop. Check out www.watch-me-paint.com! |
$1,065 | Book |
| Thursday Sept 21 |
Sunday Sept 24 |
3 | AUTUMNAL EQUINOX WEEKEND – Recharge with a few days of fall colors and cool breezes. | $925 | Book |
| Monday Sept 25 |
Saturday Sept 30 |
5 | CATCH THE COASTLINE – Enjoy the visual and culinary feasts that mid-coast Maine has to offer with its iconic lighthouses, freshly-caught lobster, and beautiful island views. | $1,125 | Book |
| Sunday Oct 1 |
Thursday Oct 5 |
4 | FALL COLORS IN FULL SWING – Watch the vibrancy of the season unfold upon the coastline. | $1,025 | Book |
| Friday Oct 6 |
Monday Oct 9 |
3 | COOL DAYS AND COZY NIGHTS – The name says it all! Break out your wool sweaters as we cozy up to the woodstove and savor the flavors of fall. | $875 | Book |
| Tuesday Oct 10 |
Saturday Oct 14 |
4 | THAT’S IT FOR 2023! – Join us for our last hurrah of 2023. We’ll see you again in 2024! | $1,025 | Book |
Full Moon
* = Capt. John Foss will join us for this trip
& = 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.
