Sunset Sail Aboard the Historic When and If

Based on 29 reviews

Set sail on a 2-hour sunset sail on Key West’s most elegant historic schooner. When And If, built in 1939 for General George Patton’s dream of sailing around the world “When and If” he was able, is available to the public for the first time in the yacht's lifetime. Sit back and experience the beautiful Key West sunset in style as the wooden schooner glides through the water driven by wind power alone. Meet the crew as they serve up a beautiful array of gourmet cheeses and share their stories of Key West and the sea.

Activity Highlights

  • Relaxing sunset cruise aboard the classic 1939 When and If schooner
  • Explore Key West's historic sights and scope regional wildlife
  • Take a turn sailing this beautiful yacht on the open water
  • Complimentary ice, bottled water, and soft drinks, La Croix, and gourmet cheese platter

What's Included

  • Cooler and complimentary ice for the drinks you bring
  • Soft drinks, bottled water, La Croix, and complimentary gourmet cheese platter
  • Free shuttle service to and from the Stock Island Village Marina
  • Views of local attractions like Mallory Square, Fort Zachary Taylor, and the old Customs House

What to bring

  • Bring sunscreen and a jacket as it can be cooler on the water than on-shore.
  • Please bring a valid, government-issued photo ID.
  • Customers may want to bring a camera and bring sunglasses.
  • Bring your own adult beverages and snacks.


  • Boats are not wheelchair accessible.
  • Must be 21 to consume alcohol.
  • Children under 18 must be accompanied by an adult.
  • Glass bottles are not allowed on the boats.

Additional information

  • Parking available for free on site.
  • Fresh tropical fruit plate & snacks are $25(1-6 guests) and $35(7-10 guests)
  • The When and If Yacht is a wooden 1939 John Alden schooner.
  • The crew is First Aid, CPR & AED certified.

Cancellation policy

Customers may cancel at least 48 hours prior to their arrival date and time will receive a full refund minus a minus a 10% processing fee plus a $5 service fee. Customers that cancel after the 48 hour period will receive a refund minus 20% plus a $5 service fee. If the weather is unfavorable, the experience may be rescheduled for a later time/date by the vendor or a full refund will be issued. No-shows will not be refunded. Customer may make changes to the reservation without any fees as long as it's outside the 48 hour cancellation period.

Check Availability/Book online
  • Susan T. about 29 days ago

    Our sunset cruise on the When and If was the best we've ever taken and the high point of our Key West trip. Friendly and helpful crew, amazing schooner,... Read More on Yelp

  • Richard S. about 1 month ago

    Was the highlight of our week in the Florida Keys. Would highly recommend this adventure on this old sailboat built in 1939. The crew were fabulous! Thanks Read More on Yelp

  • Heather A. about 1 month ago

    We did a private sunrise sail for two. It was beautiful. Captain Cody was fantastic. He told us about the history of the area and how the boat worked. We... Read More on Yelp

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