There’s no more intimate way to experience the New York skyline than by boat, which makes Manhattan by Sail a great option for your next romantic outing. Climb aboard the schooner Shearwater, New York’s only floating landmark, and you’ll be immediately immersed in Roaring Twenties elegance. Teak and mahogany provide classy backdrops, but you’ll be drawn to the glamour of unfurled sails. Once you hit open water you’ll unwind instantly, wind in your hair and the grid left completely behind. The upbeat crew will help you set the mood with bubbly from the bar. As the sun sets, the lights of Manhattan come aglow, and you’ll get vantages of the Statue of Liberty from the harbor’s front row seats. Pull your date closer as you ride the waves. Picturing Jay Gatsby yachting past in the other direction shouldn’t be too hard to do.