The stunning ambiance is just the tip of the iceberg at Pilot, where the bar has been placed on the deck of a restored 1920s racing schooner by brothers Alex and Miles Pincus, who are responsible for Seaworthy, Island Oyster and Grand Banks—the latter another floating bar. Pilot features two wraparound bars with stools (done in nautical décor, natch), a marble oyster bar at the front of the boat, and a cocktail bar near the stern. The rest of the boat is lined with white tables and folding chairs, providing ample seating. A yellow-and-white striped canopy provides shade. Chef Kerry Heffernan (of Eleven Madison Park fame) serves up ocean-inspired treats to complement the cocktails, beer and wine—like a tomato and watermelon salad, scallop ceviche, a lobster roll and a softshell crab po’boy.