Gloucester Schooner Festival & Race

Two large sailboats with white sails on the water, displaying American flags against a partly cloudy sky.

We’re excited to announce that the Schooner American Eagle will be offering daysails again for the 2026 Gloucester Schooner Festival and Race.

Join us for a two-hour sail, lunch sail, or for the Parade of Sail and Mayor’s Race for the Esperanto Cup aboard the few remaining Gloucester Schooners.

Three weathered boats docked at a pier, with a sign reading 'GLOUCESTER HOUS' and a colorful umbrella in the background, under a partly cloudy sky.

Friday, September 4th

10 AM - 2 PM

Join us for a 4-hour daysail on Friday with lunch provided. Help set sail for a harbor cruise as the American Eagle makes her return to her home of Gloucester, where she fished out of for 50 years.

Trip will be departing from the I4C2 Docks at 65 Rogers St, Gloucester, MA 01930. Please arrive at the docks at least 15-30 minutes early so that we can board and be ready to depart the dock on time.

Please note: While we will not be serving any alcohol on these trips, guests are permitted to bring their own food and drink on sails.

Join us for a 2-hour daysail on Friday. Help set sail for a harbor cruise as the American Eagle makes her return to her home of Gloucester, where she fished out of for 50 years.

Trip will be departing from the I4C2 Docks at 65 Rogers St, Gloucester, MA 01930. Please arrive at the docks at least 15-30 minutes early so that we can board and be ready to depart the dock on time.

Please note: While we will not be serving any food or alcohol on these trips, guests are permitted to bring their own food and drink on sails.

4 PM Sail

Saturday, September 5th

10 AM- 2 PM

10 AM Lunch Sail
Black and white photo of a vintage sailboat docked near a building on the water.

Friday, September 4th

4 PM- 6 PM

10 AM Lunch Sail
Race Day Sail

Spend the day aboard the American Eagle as we set sail from the schooner’s original home of Gloucester on a four-hour trip.

Enjoy a classic windjammer lunch cooked on our woodstove while sailing among other historic schooners and enjoying the coast.

Trips will be departing from the I4C2 Docks at 65 Rogers St, Gloucester, MA 01930. Please arrive at the docks at least 15-30 minutes early so that we can board and be ready to depart the dock on time.

Please note: While we will not be serving alcohol on these trips, guests are permitted to bring their own on the sails.

Saturday, September 5th

4 PM- 6 PM

Join us for a 2-hour daysail on Friday. Help set sail for a harbor cruise as the American Eagle makes her return to her home of Gloucester, where she fished out of for 50 years.

Trip will be departing from the I4C2 Docks at 65 Rogers St, Gloucester, MA 01930. Please arrive at the docks at least 15-30 minutes early so that we can board and be ready to depart the dock on time.

Please note: While we will not be serving any food or alcohol on these trips, guests are permitted to bring their own food and drink on sails.

4 PM Sail
A black-and-white historic photograph of a large ship on the shore with many people gathered around, possibly during a rescue or launch event.

Sunday, September 6th

9 AM- 4 PM

Parade of Sail and Schooner Race

Relive the excitement of the International Fisherman’s Race as the Schooner American Eagle competes in the Mayor’s Race for the Esperanto Cup.

The day begins with the Parade of Sail. We’ll leave the dock and set sail with the rest of the fleet as we make our way from the Inner Harbor to the starting area.

Before the race, enjoy a delicious lunch cooked in our galley on our classic woodstove. The race will begin at 1:00 PM, with the course decided that morning.

Trips will be departing from the I4C2 Docks at 65 Rogers St, Gloucester, MA 01930. Please arrive at the docks at least 15-30 minutes early so that we can board and be ready to depart the dock on time.

Please note: While we will not be serving alcohol on these trips, guests are permitted to bring their own on the sails.