Weekly Prize

Sunset Wine and Jazz City Sail

All aboard! Hop on the Clipper City Tall Ship or the Shearwater Classic Schooner for a cityside cruise on a historic vessel while enjoying drinks and live music. When you’re sailing along the skyline at sunset, you can let the hustle of the city melt into the cool rhythms of jazz. It’s a night made for romance, dancing, and toasting to stunning New York City views.



  • Embark on a sunset cruise with live music, drinks, and plenty of photo ops
  • Set sail in a historic vessel and enjoy stunning views of the New York City skyline from the water 


General Info

  • Tickets include access to the cruise and up to 3 glasses of wine, beer, or soft drinks
  • Date: Tuesdays, Wednesdays, and Thursdays (selected by winner based on availability)
  • Various time slots available (selected by winner based on availability)
  • Duration: 90 minutes
  • Venue: Clipper City Tall Ship, Pier 35 on the East River Waterfront, New York, NY 10002; or Shearwater Classic Schooner, North Cove Marina at Brookfield Place, New York, NY 10280
  • Must be 21+ with valid ID to access. Individuals are required to follow state and local COVID-19 guidelines and any additional safety measures implemented by each individual business.


This offering is a potential prize for our New York weekly drawing and will be awarded following Week 1. You only need to enter the sweepstakes once for a chance to win this date experience prize. See the Official Rules for more details about submission and eligibility.

The New York sweepstakes entry period has ended.

Date: December 31, 1969
Time: 4:00 pm
Location: 299 South Street Pier 35 NY 10002

Get access to this exclusive event by showing your Bumble profile. Don’t have Bumble?

Other date experience prizes nearby:
View More