Key West Historic Schooner When And If Sunset Cruise

4.8 (144 reviews) 2 hours Free cancellation

out of 5

144 reviews

4.8

Schooner When And Sunset Sail, Key West — Photos: the activity supplier, via Viator

Sail When And If — Photos: the activity supplier, via Viator

About this activity

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.

Sailing Private and Luxury Sunset Cruises Historical Tours Water Tours Excellent Quality DSA non-compliant Low Supplier Cancellation Rate

At a glance

Duration: 2 hours
Confirmation: Instant confirmation
Ticket: Mobile or paper ticket accepted
Group: Up to 28 people
People per booking: 1–15
Operated by: Sunset Sail Key West

Ages: Children (0–11 years) · Adults (12–95 years)

What is included

Included

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

Not included

Not included: Gratuities
Not included: Private transportation: Transportation to and From Vessel
Not included: Ships Souvenirs Available for Purchase Onboard

Itinerary

Stop 1

2 hours Admission 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

Passing 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

Passing by

We sail past the famous sunset celebration at Mallory Square
Opal Spa - Sunset Key Cottages

Passing 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 point and pickup

Everyone meets at the meeting point.

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.

Cancellation

Free cancellation

For a full refund, cancel at least 24 hours before the scheduled departure time.

If you cancel	You get back
At least one day before	100%
Less than a day before	0%

The operator may cancel if the weather does not allow it; you then get another date or your money back.
The operator may cancel if too few people book; you then get another date or your money back.