Boston's Premier Event Venue

Dining DeckThe Dining Deck has seating for 250 guests for a sit down dinner. Both buffet and platted dinner options available from our onboard catering.

  • Seating for 250 Guests
  • Two (2) Restrooms
  • Outdoor Rear Balcony
  • Elevator with Hadicap Access
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Lounge DeckThe Lounge Deck has open space for dancing, food service, cocktail tables and other event activities. This deck also has couch seating as well as outdoor space on both the forward and back. A full bar is located in the center of the room serving beer, wine and mixed drinks.

  • Cocktail & Lounge Seating
  • Two (2) Restrooms
  • Outdoor Forward & Rear Balcony
  • Elevator with Hadicap Access
  • Full Bar

Top DeckThe Top Deck is really what sets Sir Winston apart as an event venue. It offers uninterrupted 360 degree views of the Boston Harbor. The space is partially covered with outdoor heating incase of inclement weather.

  • Cocktail & Couch Seating
  • Two (2) Restrooms
  • Outdoor Heating
  • Elevator with Hadicap Access
  • Full Bar

Dining Options

Sir Winston's catering partners have specialize in creating memorable and unique menus that are sure to be as delicious as they are beautiful. Food is one of the most important parts of any event and Sir Winston never disappoints. We provide both plated sit down options as well as buffet style. 

Buffet & Plated Meals

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Appetizer options are available in addition to our full meals. We offer a wide variety of options to be served alongside our buffets & plated menus or to be enjoyed on their own. Our selections are the perfect size for parties of any size. If we don't have something you like our partners can create special dishes. 


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Need something one of a kind for your wedding? Sir Winston works with our local and national partners to offer a wide selection of unique items and options. An oyster bar, lobster bake and high end carving stations are just a  few examples the special event catering options we have provided.


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Bar Selection

  • Bud Light
  • Corona
  • High Noon
  • Noca
  • Sam Summer


  • Moet Chandon
  • Prosecco
  • Veuve Cliquot


  • Cabernet Sauvignon
  • Chardonnay
  • Pinot Grigio
  • Red Blend
  • Sauvignon Blanc


  • Aperol
  • Bacardi
  • Bombay Dry
  • Casamigos
  • Don Julio
  • Dr. McGillicuddy's
  • Fireball
  • Hendricks
  • Hennessy
  • Jack Daniels
  • Jameson
  • Johnny Walker Black
  • Macallan 12
  • Makers Mark
  • Patron
  • Titos


Let's Get Connected

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