Gloucester Schooner Festival. See the schooners with Cape Ann Cruises aboard the vessel Wejack. Private Charters in Gloucester MA picture up to 46 passengers.

Gloucester Schooner Festival Schedule of Events 2025 Calendar - Cruise Schedule aboard WEJACK to View the Schooners, Schooner Races, Boat Parade of Lights, Gloucester Fireworks, and Parade of Sail

Plan ahead. Purchase tickets below to ensure your spot aboard the Wejack to spectate the following events before they sell out!

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, August 28th, 2025

Friday, August 29th, 2025

  • 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, August 30st, 2025

  • Schooner Festival Sunset Scenic Cruise Gloucester Harbor: Departs at 6PM 7:30PM - details & tickets

  • 8PM - FIREWORKS Cruise Gloucester Harbor [low ticket alert] - Departs 8:00PM details & tickets

Sunday, August 31st, 2025

  • 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 1st, 2025