How to See the Schooners with Cape Ann Cruises
Join us aboard the legendary Gloucester Fishing Yacht, the Wejack to see all the visiting Schooners up close from the water. The Wejack has a full bar aboard. We have multiple trips offered daily during the Schooner festival that will be a boatload of fun! See the Calendar and schedule of events below to learn more about our trips offered for the Schooner Festival. The Wejack is a classic power/fishing vessel that you’ll fall in love with, and is not a schooner., but is the perfect spectator boat to get the best views.
Schedule of Events – Cruise Tickets
Thursday, September 3rd, 2026
Schooner Challenge Race -5:30-7:30PM – Buy Tickets
Friday, September 4th, 2026
See the Schooners & Scenic Harbor Tour 12:00 PM – 1:30 PM – Buy Tickets
See the Schooners & Scenic Harbor Tour 3:30 PM – 5:00 PM – Buy Tickets
See the Schooners, Sunset & Scenic Harbor Tour 6:00 PM – 7:30 PM – Buy Tickets
Saturday, September 5th, 2026
See the Schooners & Scenic Harbor Tour 12:00 PM – 1:30 PM – Buy Tickets
See the Schooners & Scenic Harbor Tour 3:30 PM – 5:00 PM – Buy Tickets
Schooner Festival Sunset Scenic Cruise Gloucester Harbor: Departs at 6PM 7:30PM – details & tickets
8PM – FIREWORKS Cruise Gloucester Harbor – Departs 8:00PM details & tickets
Sunday, September 6th, 2026
Parade of Sail Cruise Departs at 9:30 AM details & tickets
Mayor’s Cup Race – Departs at 12:30 PM details & tickets
See the Schooners – Scenic Gloucester Harbor Cruise Departs at 3:30 PM details & tickets
See the Schooners at Sunset – Departs at 6 PM details & tickets
Monday, September 7th, 2026 – LABOR DAY
See the Schooners – Scenic Gloucester Harbor Cruise Departs at 12 PM details & tickets
See the Schooners – Scenic Gloucester Harbor Cruise Departs at 3:30 PM details & tickets
See the Schooners at Sunset – Departs at 6 PM details & tickets
Upcoming Events on the
Newburyport/Rockport Line
LET GO An Exhibition Featuring Benjamin Herbert, Kathleen Gerdon Archer, and Janice Colby
June 25 @ 12:00 pm - July 19 @ 5:00 pm
Newburyport Art presents May Exhibitions at 65 Water Street
July 15 @ 11:00 am - 5:00 pm
Newburyport Art present July Exhibitions & Events
July 15 @ 11:00 am - 5:00 pm
LET GO An Exhibition Featuring Benjamin Herbert, Kathleen Gerdon Archer, and Janice Colby
July 15 @ 12:00 pm - 5:00 pm
Birdseye Rooftop Live Music Access
July 15 @ 6:00 pm - 9:00 pm