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 2026 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, September 3rd, 2026

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 [low ticket alert] - Departs 8:00PM details & tickets

Sunday, September 6th, 2026

Monday, September 7th, 2026 - LABOR DAY