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 starting TBD
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
Friday, June 19, 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.

Father’s Day Sail
Sunday, June 21, 2026
TBD
Happy Father’s Day! Fathers sail free when accompanied by the purchaser of one full priced ticket. Limit one dad per full priced ticket purchase. Cannot be combined with other offers/discounts.

3rd of July Fireworks Cruise
Friday, July 3, 2026
Enjoy the spectacular Gloucester Fireworks from a front row seat aboard the Schooner Ardelle!

Sail Boston 250

Ardelle Sail Boston 250 Parade of Sails
Saturaday, July, 11, 2026
8:00AM – Parade End

Isabella Sail Boston 250 Parade of Sails Private Charter
Saturday, July 11, 2026
8:00 AM – Parade End

Ardelle Sail From Gloucester to Sail Boston 250
Friday, July 10, 2026
12:30 – Arrival in Boston
Join us as we set sail to Boston for Sail Boston 250!
We will depart Gloucester and sail along the scenic coast of the northshore to our dock in Boston (tentatively the Moakley Courthouse Dock).
Along the way we will have the opportunity to sail through the visiting fleet of Tallships anchored as they await the Parade of Sail into Boston Harbor on Saturday morning.

This is a one way trip, and passengers are responsible for their own transportation back to Gloucester.

Isabella Private Charter from Gloucester to Sail Boston 250
Friday, July 10, 2026
11:30 AM – Arrival in Boston
Join us as we set sail to Boston for Sail Boston 250!
We will depart Gloucester and sail along the scenic coast of the northshore to our dock in Boston (tentatively the Moakley Courthouse Dock).
Along the way we will have the opportunity to sail through the visiting fleet of Tallships anchored as they await the Parade of Sail into Boston Harbor on Saturday morning.

Isabella Sail Boston 250 Fireworks Private Charters
Saturday, July 11 & Wednesday, July 15
8:3opm
Charter your own private schooner for the fireworks show! Enjoy the spectacular Sail Boston Fireworks on an intimate private charter aboard the Schooner Isabella.

Ardelle Sail Boston 250 Fireworks Sail
Wednesday, July 15, 2026
8:30 PM

Ardelle Sail From Gloucester to Sail Boston 250
Thursday, July 16, 2026
8:00 – Arrival in Gloucester
Join us as we set sail from Sail Boston 250 home to Gloucester!
We will depart Boston and sail along the scenic coast of the northshore to our dock at Maritime Gloucester.
Along the way we will have the opportunity to sail with the departing fleet of Tallships.

Isabella Private Charter from Sail Boston 250 to Gloucester
Thursday, July 16, 2026
8:00 AM – Arrival in Gloucester
Join us as we set sail from Sail Boston 250 home to Gloucester!
We will depart Boston and sail along the scenic coast of the northshore to our dock at Maritime Gloucester.
Along the way we will have the opportunity to sail with the departing fleet of Tallships.

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
8:15pm
Enjoy the spectacular Gloucester Schooner Festival Fireworks from a front row seat aboard the Schooner Ardelle!