Special Events

Special Event sail tickets are added regularly throughout the season as our schedules are confirmed. Our sail schedule is subject to change until a ticket is purchased. Please check back if you do not find an open availibility for the event you are interested in at this time.

Weekly Events

Celtic Music Sunset Sail with Michael O’Leary & Friends
Sundays, Beginning May 24, 2026
6:00-8:30 PM*
Craic* on deck! Join singer Michael O’Leary & Friends for a sailing céilidh of traditional tunes, songs ‘n sea shanties aboard the schooner Ardelle as she takes a sunset sail around beautiful Gloucester harbor. The seven musicians are an array of tune players and singers from Cape Ann, the North Shore and greater Boston. *Irish for Fun!

Schooner Challenge
Tuesdays 
6:00-8:00PM
Help us raise anchor, set the sails, and best our rivals! We will be joined in the Challenge by several of the schooners participating in this year’s festival.
This will be a great opportunity to take photos of visiting schooners as we welcome them to Gloucester for Schooner Festival Weekend!

Upcoming Special Events

Cape Ann Circumnavigation Sails
Monday, August 17, & Wednesday, September 16, 2026
8:00 am – 3:00 pm
These full day sails are perfect for those who would like to spend the day sharing sea stories, viewing the diverse land and seascapes of Cape Ann, seeing lighthouses, or just relaxing out on the water. If time allows we will stop in at Rockport for some time ashore or sail into the hole-in the wall at Lane’s Cove. Circumnavigation trips depart from Maritime Gloucester at 8am and return at 3pm (plus or minus) and offer those who come along a chance to really enjoy the Ardelle on an extended trip!
If the weather allows we will circumnavigate Cape, if not, we will head down to some other coastal community or off shore for a whale watch. Bring a picnic lunch and we will provide coffee and donuts and a lot of fun! Adults (16+) only.

Gloucester Schooner Festival 2026

Gloucester Schooner Festival Parade of Sails
Sunday, September 6, 2026 
9:30- 11:30am

Join us as we participate with over 30 Schooners in the Gloucester Schooner Festival Parade of Sail! A great opportunity to see the schooners up close and photograph this spectacular event!

Sail is 2-hours and does not include the Schooner Race.

Gloucester Schooner Festival Fireworks Sail
Saturday, September 5, 2026
8:00pm
Enjoy the spectacular Gloucester Schooner Festival Fireworks from a front row seat aboard the Schooner Ardelle!

Schooner Festival Schooner Challenge
Thursday, September 3, 2026
5:30-7:30pm
Help us raise anchor, set the sails, and best our rivals! We will be joined in the Challenge by several of the schooners participating in this year’s festival.
This will be a great opportunity to take photos of visiting schooners as we welcome them to Gloucester for Schooner Festival Weekend!

Gloucester Schooner Festival Greet the Fleet 
Thursday, September 3 & Friday, September 4, 2026 
12:30-2:30 pm & 3:00 pm – 5:00pm
Join us as we welcome visiting schooners to Gloucester Harbor for the 2024 Gloucester Schooner Festival!
A great opportunity for  schooner fanatics and photographers!

Isabella Gloucester Schooner Festival Fireworks Privae Charter
Saturday, September 5, 2026
8:oo pm
Enjoy a private charter for the spectacular Gloucester Schooner Festival Fireworks aboard the Isabella. 
6 Passenger Max