Key West Sailing Charters & Tours

Set sail on Key West’s most elegant historic schooner, the When and If. Built in 1939 for General George Patton’s dream of sailing around the world “When and If” he was able, is available to the public for the first time in the yacht's lifetime. Sit back and experience the beautiful Key West sunset in style as the wooden schooner glides through the water driven by wind power alone. Meet the crew as they serve up a beautiful array of gourmet cheeses and share their stories of old Key West and the sea. Book your Sunset Sail today!

Cruise the scenic water of America's southernmost city on a private day sail adventure with the professionals at Sunset Sail Key West. From the history of Mallory Square and Fort Zachary Taylor to the natural beauty of Key West's National wildlife preserve, this comprehensive sightseeing cruise is the perfect way to experience picturesque sailing in Key West with your family or friends. Relax with a drink, take in the scenery, or test your hand at sailing the ship! Don't miss the fun, book today!

Climb aboard a 65-foot historic Schooner for a luxurious experience that has been rated one of the top two sunset tours in all of North America by Coastal Living Magazine. Join this unforgettable Wind & Wine Sunset Sail in Stock Island, Florida! Embark on this journey and indulge your senses with a selection of wines and light appetizers that beautifully pair. Whether you're a wine enthusiast, a sunset lover, or simply seeking an exceptional experience, this journey promises to exceed your expectations. Book your experience today!

Come along on this Champagne Sunset Sail and step into luxury in Key West, Florida. Sip, relax, and unwind aboard a gorgeous wooden schooner. Enjoy your authentic sailing experience as you cruise the crystalline water to landmark sites while sampling a wide variety of complimentary drinks. Come toast to an idyllic Key West sunset on the schooner cruise that is sure to become your favorite new Key West tradition. Book yours today!

Spend a romantic evening aboard an authentic wooden schooner on this Windjammer Schooner Sunset Sail in Key West, Florida. This sailing vessel is fit for royalty, with its wide decks and ample seating and includes an open bar. Journey in comfort to landmark sites like the Navy Mole, Fort Zachary Taylor, Sunset Key, and more as the sails are hoisted and the tropical breeze whisks your cares away. Witness the beauty of a Key West Sunset and behold the grandeur of the star-filled Southern sky on this cruise. Book today!