When you’re looking for something truly spectacular to do together, consider booking a private sailing charter with Sail Sunset. This 1982 37 foot O’Day owned and operated by Captain James Brooks can comfortably seat up to six people, aka three awesome New Yorker couples. The charters are available morning, afternoon, and evening (we vote for the sunset sail) and take you on a stunning trip around lower Manhattan with great views of the city and a close pass by the Statue of Liberty.