Key West is famous for its circus-style sunset celebration on Mallory Square. For a more upscale (and less crowded) experience, hop on Danger Charters Wind and Wine Sunset Sail, where you'll have a peaceful front row seat to the sun's departure, replete with world-class wines. Each cruise is limited to a maximum of 25 people, which creates an intimate cocktail party vibe. Eight different fine wines, a selection of cheese, fresh fruits, beer, and hors d'oeuvres are served aboard the Danger Prize, a 65-foot schooner. A mellow mix of reggae, Jimmy Buffet, Salsa and Bossa nova music plays over the speakers in rhythm with the wind rippling the canvas sails. As the sun slips below the horizon, keep an eye out for the Keys' mystical green flash.