June 17th 2022

2 Hour Harbor Cruise

Experience Boston Harbor from the water. Our 2 hour cruise tours Boston's inner harbor and also includes a relaxing painting session. Drinks and light concessions available to purchase at one of our full bars.

Friends & Families

This event is for guests of all ages. Enjoy time inside our climate controlled interior lounge or outside on our heated deck. 

Cruise Schedule

  • Boarding Starts at 6:30 PM
  • Departure at 7:00 PM
  • Return to Dock at 9:00 PM
  • Cruise Concludes at 9:15 PM


Enjoy a sunset cruise aboard the Sir Winston, while talented artists teach you how to create your very own masterpiece. Begin your night with a drink on our top deck before making your way downstairs for a 90 minute painting session. Professional photographers will capture photos for guests to enjoy online after the cruise. All Guests will also get to bring their paintings home!

We Set Sail In:

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The Sir Winston

Indoor Lounge

Top Deck