We're in Downtown Key West! Call to book or book online nowWinter in Key West!Book online now...or call us for your ticket Check out our online store......and order before 12/18 for shipping in time for Christmas! Our star products are our new buff/face coverings and gorgeous 2021 When And If calendars but have a look at all our fab swag and get shopping!COMING SOON: Wreckers Race Sailing 2021!Daysail in Key West, FL Tropical Winter SailingSunset Sails in Key West Winter in the Keys!Our Winter Hosts Sunset Sail Key West Book online or call to enquire Winter sailing in Key West book sunset tickets here Visit sunset sail Key West Sunset Sails. Day Sails. Private Charters. Regattas. Special Events.General Patton's gorgeous 1939 wooden schooner is sailing out of Key West, FL every day. Book your Key West sunset sail here Book Your Perfect Florida Keys Sailing ExperienceEnjoy a day sail, or Key West's most elegant and exclusive Sunset Sail on this historic classic yacht!Built for General George Patton in 1939, When And If is open to the public for the first time in her history.Help raise sail, take the helm or sit back and relax with our complimentary Schooner Wine and select beers - don't forget to ask about our Beverage Upgrade! reservations Click here to call and enquire about chartering When and If.We know you'll have lots of questions so don't be shy!An Historic VesselWelcome Aboard!Sailing SchedulePrivate charter on When and If in NYC WHEN AND IF, NYC from Caleb Seppala on Vimeo.Private charter on When and If in NYC WHEN AND IF, NYC from Caleb Seppala on Vimeo.When and If sailing from Key West, FL to Havana, Cuba Key West to Cuba from Caleb Seppala on Vimeo.When and If sailing from Key West, FL to Havana, Cuba Key West to Cuba from Caleb Seppala on Vimeo.When and If at the Great Chesapeake Bay Schooner Race, 2015 When And If from Caleb Seppala on Vimeo. When And If from Caleb Seppala on Vimeo.