The Clipper City Twilight Sail from Manhattan by Sail is a two-hour sail that offers a unique setting aboard a 158-foot-long tall ship and dazzling views of the Brooklyn Bridge, Statue of Liberty and other New York City landmarks against the constantly shifting backdrop of a beautiful evening sky. The slow glide of the Clipper City around New York Harbor coincides with the setting of the sun, allowing camera-toting passengers to snap picturesque scenes as the sky turns from light blue to pink-tinged orange to inky indigo during the course of this leisurely cruise. The trip is made even more pleasant by the presence of a friendly crew, who are happy to chat with passengers about their beloved Clipper City or answer questions about the art of sailing in general. Shortly after the Clipper City departs from South Street Seaport, the crew invites all aboard to help hoist the massive sails. This makes for a particularly memorable moment, as the masts and rigging stretch to a dizzying height of 120 feet above the deck. Passengers may enjoy celebrating such a spectacular occasion with a drink that can be purchased at the bar, where a couple of amiable bartenders stand ready to mix up nautically-inspired cocktails or, for those who prefer, they’ll happily pour a glass of wine, beer, soda or juice. Those in the mood for music may want to linger on the adjacent benches and listen to the steady stream of tunes being piped in from speakers above the bar. A quieter ambiance can be found on the raised quarter deck at the rear of the Clipper City, which offers additional seating, equally beautiful views and an up close look at the captain in action. Given the ample size of its decks, the Clipper City provides plenty of room for passengers to sprawl out and enjoy the views. With freedom to move about Clipper City throughout the duration of the cruise, passengers can enjoy the scenery of the New York Harbor from various vantage points. The setting sun makes for dramatic shifts in the views around you, providing a fantastic opportunity to witness the iconic Manhattan skyline and other familiar sights start to sparkle as darkness falls.