Special Events

Special Events Calendar & Tickets

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.

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.

Upcoming Special Events

Celtic Music Sunset Sail with Michael O’Leary & Friends
Sunday, July 31
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!

Sunset History Sails with Local Historian Justin Demetri
Wednesday, August 3rd
6:00-8:00 pm
Join us for an evening of sea stories as we explore the history of Gloucester’s iconic working waterfront with local historian and author Justin Demetri.
Growing up “Down the Fort” in one of the many families that comprised Gloucester’s Italian fishing fleet, Justin spent his childhood among the fishermen, the boats and the wharves. Justin’s friendship with author and historian Joseph E. Garland sparked his love of writing, and appreciation for the special place he still calls home. Justin holds a degree in Cultural Anthropology from the University of Massachusetts/Boston and is the Historian at Maritime Gloucester. 

Sunset Music Sail with Marina & Berna
Thursday, August 4
6:00-8:00 pm

Marina and Berna are an international folk/americana duo who divide their time between Marina’s native New England and Bernardo’s native Italy. Combining Marina’s sultry vocals & unusual melodies with the raw, gritty edge of Bernardo’s slide guitar, soulful voice, and the sweet interjections of his mandolin, the duo’s sound has been refined over years together on the road, the stage, and in the studio. Together the pair has captivated audiences across the United States and in Europe, and is now at work on their fourth original record.

Sunset Music Sail with Daisy Nell & Captain Stan
Thursday, August 18, 2022
6:00-8:00 PM
Daisy Nell & Captain Stan & the Crabgrass band specialize in traditional and contemporary songs of the sea and shore, with local Cape Ann flavor and lore.

Daisy Nell, native of Essex, MA, mainstay of the shipbuilding industry for over 300 years, brings alive New England’s maritime history through traditional songs of the sea. A familiar voice on the North Shore music scene, she is known for her broad repertoire of traditional folk, chanteys, and contemporary songs.

Cape Ann Circumnavigation Sail
TBD
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.

Schooner Challenge
Thursday, September 1, 2022
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!

Greet the Fleet Sail
Friday, September 2, 2022
Join us as we welcome visiting schooners to Gloucester Harbor for the 2022 Gloucester Schooner Festival!
A great opportunity for  schooner fanatics and photographers!

Heritage Day 1-Hour Sails
Saturday, September 3, 2022
The best deal of the weekend! Join us for a one hour sail in Gloucester Harbor to see the visiting schooners during Maritime Gloucester’s annual Heritage Day Celebration!

Gloucester Schooner Festival Fireworks Sail
Saturday, September 3, 2022
Enjoy the spectacular Gloucester Schooner Festival Fireworks from a front row seat aboard the Schooner Ardelle!

Gloucester Schooner Festival Parade of Sails
Sunday, September 4th, 2022 (Rain Date Monday, September 5)
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.