Share this tour
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
Meeting and pickup
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.
Itinerary
-
1
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 -
(Pass by)
Sailing through the National Marine Sanctuary offers the unique opportunity to view marine wildlife. Sea turtles, bottle nose dolphin and marine birds.
Admission ticket free
Additional info
- 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
Tags
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Show more
Cancellation Policy
- For a full refund, you must cancel at least 24 hours before the experience’s start time.
- If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the experience’s start time will not be accepted.
- This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
- This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Rating
You can cancel up to 24 hours in advance of the experience for a full refund.
Your guide to the flawless travel experience
Top Searches
Company
Get our app
