Gloucester Schooner Festival Schedule of Events 2023 Calendar During the Gloucester 400th Celebrations - 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 31, 2023

Friday, September 1st, 2023

  • See the Schooners & Scenic Harbor Tour 12:00 PM (noon)- 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 2nd, 2023

  • See the Schooners & Scenic Harbor Tour 12:00 PM (noon) - 1:30 PM Buy Tickets

  • See the Schooners & Scenic Harbor Tour 3:30 PM - 5:00 PM - Buy Tickets

  • Parade of Lights & Sunset Scenic Cruise Gloucester Harbor: Departs at 6PM - details & tickets

  • 8PM - Fireworks Cruise Gloucester Harbor (SOLD OUT) - Departs 8:00PM details & tickets

Sunday, September 3rd, 2023

Saturday September 9th, 2023

  • Organically Good Trio - Departs at 5:30 PM details & tickets - Reggae based trio with members of Slightly Stoopid, John Brown’s Body and Dub Apocalypse!

Come Join us aboard the Classic Fishing Yacht the WEJACK to view the beautiful schooners while cruising the waters of scenic Gloucester Harbor. Watch the Schooner Challenge, Parade of Sail, Mayor's Cup Race, Boat Parade of Lights, Fireworks and more throughout the Gloucester Schooner Festival. The best way to see the schooners is from the water!

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