Key West Historic Schooner When And If Sunset Cruise

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champagne glass as the sun dips below the horizon, while your experienced crew handles the sails — or try your hand at steering this classic wooden schooner yourself. Glide along turquoise waters, spot playful dolphins and local wildlife, and enjoy an unforgettable evening that blends history, luxury, and adventure. Highlights: Historic schooner experience aboard the When And If, commissioned by General George Patton in 1939. Champagne sunset toast included Elegant and exclusive cruise - Avoid the crowds Hands-on sailing opportunity: take the wheel under guidance from your experienced crew. Spot dolphins, sea birds, and local marine wildlife. Perfect for romantic evenings, family adventures, or history enthusiasts — children sail at a discounted fare.

1. 1

   Stop 1

   2 hours

   Vessel is docked at the Key West Historic Seaport at the end of E dock which is in front of the Waterfront Brewery. Look for the E sign on the dock piling and walk down to the end of that long pier. The schooner has varnished wooden masts with flags at the top of each mast. Check in and boarding happens directly at the boat and begins 15 minutes prior to departure.

2. 2

   Florida Keys National Marine Sanctuary

   Pass by

   Sailing through the National Marine Sanctuary offers the unique opportunity to view marine wildlife. Sea turtles, bottle nose dolphin and marine birds.

3. 3

   Mallory Square

   Pass by

   We sail past the famous sunset celebration at Mallory Square

4. 4

   Opal Spa - Sunset Key Cottages

   Pass by

   Sail past the offshore Key West Island of the rich and famous from the comfort of your seat aboard our majestic classic yacht

• Service animals allowed
• Public transportation options are available nearby
• Infants are required to sit on an adult’s lap
• Suitable for all physical fitness levels
• Children must be accompanied by an adult

For a full refund, cancel at least 24 hours before the scheduled departure time.