Sunset Sail Key West Activities

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!

Live the Key West lifestyle as you set sail over calm blue waters then drop anchor and chill out on a giant floating lily pad. Enjoy this unique private adventure with family and friends, away from the crowds. Be sure to take in all of Key West's beauty while relaxing and soaking up the sun from the water. Book today and set out on a private sailing adventure.

Climb aboard and set out on a private snorkel and sunset sail in Key West, Florida. You'll get the best of both worlds as you glide across the water in classic sailboat before jumping in magical blue waters to snorkel and explore the underwater ecosystems off the coast of Key West. Then wrap it all up with a world famous Key West sunset. The perfect way to spend time with friends and family, book your private snorkel and sunset sail today.