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.

Itinerary

Start Point

We are docked at the end of "E" dock. E dock is on the waterfront…

Stop 1

Vessel is docked at the Key West Historic Seaport at the end of E dock…

Stop 2

Sailing through the National Marine Sanctuary offers the unique opportunity to view marine wildlife. Sea…

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…

End Point

We are docked at the end of "E" dock. E dock is on the waterfront…

What’s included

Soda/Pop
Bottled water
Select Beer and Wine Included. Sunset Champagne Toast and Bottle Service Upgrade Available
Experienced Captain and Crew
Restroom on board
Opportunity to Take the Wheel and Help Raise Sail

Not Included

Gratuities
Transportation to and From Vessel
Ships Souvenirs Available for Purchase Onboard

Additional Information

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.

Cancellation Window	Refund Eligibility
24 hours or more before start time	100% refund (Full refund)
Less than 24 hours before start time	Non-refundable (0%)

This experience may be cancelled due to bad weather. This experience may be cancelled if there are not enough travelers.

Age Policy

Child: 0–11 years · Adult: 12–95 years

Specification: Key West Historic Schooner When And If Sunset Cruise

Duration	2 Hours
Ticket Type	Mobile or paper ticket accepted
Group Size	Up to 28 travelers
Confirmation	Instant Confirmation
Boat Type	Sailboat
Activities	History & Culture
Time of Day	Sunset
Tour Type	Shared