
pancakes on schooner adventure

My View of Life on the Dock


Our Greet the Fleet sail Friday at noon and Sunday Race Day tickets have sold out already, but you can still join us Thursday evening at 5:00 for the Schooner Challenge, a friendly competition among the local vessels, and Saturday morning at 8:30 for our Heritage Day sail. Just go to schooneradventure.org and click on “Book Now”.
Don’t miss this once a year chance to get up close to the local and visiting schooners from the deck of Gloucester’s 99-year-old Flagship, the last of the dory fishing schooners.

CALLING All DESCENDANTS! THIS SAIL IS FOR YOU! Friday, August 22nd 5PM-7:30PM. Adventure has been preserved as a tribute to the hard work, sacrifice, and contributions of Gloucester schoonermen, dorymen, and their families. If you are descended from a captain or crew member from one of Gloucester’s (and beyond) many schooner fishing families, please join us for one of our annual Descendant’s Sails, offered free to the families of fishermen. We ask that you share your story with us to reserve your spot. Questions? Want to make a reservation? Please contact us directly 978.281.8079. Visit our website for all upcoming sails.








SCHOONER ADVENTURE – THE FLAGSHIP OF GLOUCESTER

Join us as we celebrate 98 years of Adventure!
SUNDAY, SEPTEMBER 15, FROM 4 – 7PM
Enjoy delicious lobster rolls, nibbles & libations during this special 3 hour sail
Tickets $98
Proceeds go towards the 2025 vessel preservation efforts. Join us as stewards of this National Historic Landmark. To purchase tickets for this and all sailing events . . .
978-281-8079 info@schooner-adventure.org
23 Harbor Loop Gloucester, MA

Join us on Gloucester’s Flagship Adventure during the Schooner Festival, lots of opportunities to sail amongst visiting schooners on the fully-restored 122′ National Historic Landmark, built in Essex in 1926.
Thursday, August 29, 5 pm – 7:30 Schooner Challenge Local schooners and early arrivals compete in a friendly evening of skills and obstacles.
Friday, August 30, 2 pm – 4:30 Greet the Fleet We will cruise outside the harbor to salute incoming boats.
Friday, August 30, 5 pm – 7:30 Public Sunset Sail A beautiful time to be on the water.

Saturday, August 31, 8:30 am – 11:00 Heritage Day Sail We will go where the wind takes us early in the day.
Saturday, August 31, Noon – 6pm Free Deck Tours Visit us at the I4C2 docks accessed from the parking lot between the Gloucester House and the Building Center. Check out our tents for merchandise and kid’s activities.

Sunday, September 1, 9:15 am – 5(ish) pm, Parade of Sail & Schooner Race Spend all day aboard as we pass the crowds on the Boulevard and sail out of the harbor to the starting line, and then compete with all the other schooners in an unforgettable maritime spectacle. Breakfast and lunch are included on board.

Tickets are still available, but these events usually sell out. Visit schooneradventure.org and click on Book Now. Boarding for all these sails from Thursday through Sunday will be from the docks at I4C2, accessed from the parking lot between the Gloucester House and the Building Center.

Adventure Calls!
New this year, Gloucester’s flagship and only National Historic Landmark vessel will be located at PierI4C2 during Gloucester’s 39th annual Schooner Festival. Sail an authentic part of Gloucester’s fishing heritage. Captain Miller-Shelley says” We’ve been preparing all season for this weekend. We’ve taken every tack and opportunity to train for the race in hopes of making the shortest time possible around the marks. I’m looking forward to the excitement and friendly competition of sailing alongside other schooners and their crews.”
For more information and tickets visit our website calendar

For more information and tickets visit our website calendar
Friday, September 1
Kick-Off Sail
10 AM – 1:00 PM
Catch a glimpse of the excitement building out on the water.
Festival Fleet Sail
1:30 – 4:30 PM
Greet the fleet as they begin to arrive.
Saturday, September 2
Heritage Day Sail
8:30 – 11:30 AM
Sail out among 28 other Schooners from around the nation.
Sunday, September 3
Mayor’s Cup Race & Parade of Sail
8 AM – 5 PM
This all day excursion complete with breakfast and lunch is the biggest sailing day of the year! Help Adventure’s captain & crew lead the parade and capture first place in the race!
Schooner Adventure is thrilled to launch sailing for the Gloucester 400+ season with sails beginning during St. Peter’s Fiesta. Adventure is inaugurating Gloucester Sails! funded in part by Beauport Financial Services and an official event of the Gloucester 400+, over the Fiesta weekend, June 23-25. During these three days, with help from Wellspring House, Gloucester Housing Authority, Open Door, and Pathways for Children, Adventure will give free sails to 350 passengers who have never sailed before!
In her 97 years sailing, this is the first time Adventure is helmed by a woman, Captain Christa Miller-Shelley. With the help of a new crew of 8 plus seasoned Mate Natalie Warren, Captain Miller-Shelley has been bending on sail, running safety drills and inspections as well as leading many a shake-down cruise in preparation for sailing in service to the community. This capable Captain impresses with her skill, tenacity, and good humor. She has been overheard saying ““I can’t wait to get the water in the scuppers!”
Adventure also offers ticketed sails to the general public for St. Peter’s Fiesta weekend:
FRIDAY JUNE 23, 10 AM – 12:30 PM – Be the First to Sail on Adventure this Season!
SATURDAY JUNE 24, 4:30 PM – 7 PM – Greasy Pole Sail! We’ll try to get a glimpse of the greasy pole challenge, one of the highlights of Saint Peter’s Fiesta.
SUNDAY JUNE 25, 3:00 PM – 5:30 PM – Blessing of the Fleet Day! GET YOUR TICKETS HERE


Spend the summer on the water as a deckhand on Adventure.
We are looking for several people 18+ to join our 122-foot schooner, sailing almost every day from the pier at Maritime Gloucester. Sailing experience is a plus but not required, sail training is part of what we do. These are live-aboard positions so room and board are part of the package along with good pay and a chance to be part of the awesome crew, sailing and maintaining our National Historic Landmark. More details are available here. Send a résumé and cover letter to Stuart Siegel, Executive Director, stuart@schooner-adventure.org.



Sunday, August 28
4:30 – 7:30 pm
Featuring Marina Evans & Bernardo Baglioni
$60 pp
Enjoy the camaraderie of friends surrounded by the beauty of Cape Ann at sunset while sailing and listening to a special performance by this international folk/americana duo.
Complimentary beverages. BYOPicnics

Local Musician, Artist, Poet and Naturalist, Corey Wrinn
will entertain passengers on Adventure Friday, July 22, 5:00 PM – 8:00 PM
Adults $60
Children 18 & under are FREE with paying adult
Complimentary wine, beer & soda included.
BYOPicnics encouraged.
Discounts for members, students, seniors, military & first responders.
For tickets visit our website ticketing calendar.