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.