Every Saturday - Starting May 28th 

2 Hour Harbor Cruise

Catch an amazing view of the sunset from Boston Harbor. Drinks are served at one of our two full bars located on our outdoor deck & indoor lounge. 

21 and Older Event

Local Boston DJs play music while you enjoy the party outside or relax in the indoor lounge. Our outdoor deck is covered and heated so the party doesn't stop, rain or shine. 

Cruise Schedule

  • Boarding Starts at 6:15 PM
  • Departure at 7:00 PM
  • Return to Dock at 9:30 PM
  • Cruise Concludes at 10:00 PM
We Cruise Every Saturday!

Saturday Sunet DJ Cruise

Sir Winston cruises EVERY Saturday this summer. View our event calander to find the perfect weekend.

  • Boarding at 6:15PM
  • Every Saturday
  • 2.5 Hour Cruise
Buy Tickets


Upcoming Special Events

The Sir Winston

Indoor Lounge

Top Deck