Key West Sunset Sail on Historic Schooner

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.

Meeting Point

7009 Shrimp Rd

7009 Shrimp Rd, Key West, FL 33040, USA

We are docked at slip H16 at the Stock Island Marina. Directly in front of the new Sloppy Joe's Dockside bar and restaurant. There is ample free parking. Please arrive 15-30 minutes before the start of the sail to ensure plenty of time to find the boat.

What's included:

• Experienced Captain and Crew
• Opportunity to Take the Wheel and Help Raise Sail

Not included:

• Ships Souvenirs Available for Purchase Onboard

What to expect:

Duration: 2 hours

Sunset Sail Key West

7009 Shrimp Rd, Key West, FL 33040, USA

Vessel is docked at the Perry Marina at slip # H16. Look for Bad Boys Taqueria and you will see the Schooner with varnished wooden masts. Check in and boarding happens directly at the boat and begins 15 minutes prior to departure.

2 hours • Admission Ticket Included

Florida Keys National Marine Sanctuary

33040, Florida

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

Pass by without stopping