Key West Historic Schooner When And If Sunset Cruise
4.8 / 5 · 144 traveler reviews
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.
Your experience
Stop 1
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.
Stop 2
Sailing through the National Marine Sanctuary offers the unique opportunity to view marine wildlife. Sea turtles, bottle nose dolphin and marine birds.
Stop 3
We sail past the famous sunset celebration at Mallory Square
Stop 4
Sail past the offshore Key West Island of the rich and famous from the comfort of your seat aboard our majestic classic yacht
What’s included
- Carbonated beverages
- Bottled water
- Alcoholic beverages
- Experienced Captain and Crew
- On-board restrooms
- Opportunity to Take the Wheel and Help Raise Sail
Not included
- Gratuities
- Private transportation
- Ships Souvenirs Available for Purchase Onboard
Meeting and pickup
We are docked at the end of "E" dock. E dock is on the waterfront boardwalk in front of the Waterfront Brewery. Check in happens at the vessel. Please arrive 15-30 minutes before the start of the sail to ensure plenty of time to find the boat.
Before you go
- 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
Cancellation policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Check the policy for your selected date and option before booking.
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