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"Maybe even go for a spin on Jane's Carousel?"
Tacky as it sounds, neither rooftop party nor loft concert can compete with the wow factor of the view from between the Brooklyn and Manhattan bridges. Seal the deal in Dumbo.
7pm: Arrive aboard the East River Ferry to heighten that “Holy shit New York City!” effect.
8pm: Whatever show is on stage at St. Ann's Warehouse (38 Water St), it’s likely very good, and without fail technically spectacular. This month it’s the Wooster Group and New York City Players doing a series of early Eugene O’Neill plays about sailors, specifically the longing of being away from those they love while at sea. How apt!
10pm: It’s at the other end of the neighborhood, but the trek to Vinegar Hill House (72 Hudson Ave) will be worth your while, specifically for its ability to transport you from the quintessential urbanness of Dumbo proper to the quaint village vibe of Vinegar Hill. It helps that the setting oozes romance, and the food is damn good too.
11:30pm: If you need to have one more trick up your sleeve (you’re doing something wrong!), grab your date by the hand and slip around the corner to check out the amazing Commandant's Mansion perched atop Vinegar Hill on Evans Street, which happens to also be a great make-out spot. Now take him/her home already!