Key West Historic Schooner When And If Sunset Cruise

Beautiful Teak and Varnished Sailing Yacht When And If

Key West Historic Schooner When And If Sunset Cruise

Duration2h

Free cancellationFull refund up to 24 hours before

Instant confirmationYour booking is confirmed right away

TicketMobile or paper ticket accepted

Group sizeUp to 28 travelers

Overview

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.

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

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

What to expect

2h · Admission ticket included

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.
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.
Mallory Square
Pass by

We sail past the famous sunset celebration at Mallory Square
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

Meeting and pickup

Meeting point

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.

End point

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.

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.

Reviews

4.8 (144)