Sunset Sail Aboard the Historic When and If

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Set sail on Key West’s most elegant historic schooner, the 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

Customer must cancel at least 48 hours in advance to receive a full refund, minus 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

Read what other TripShock! travelers think about the Sunset Sail Aboard the Historic When and If. What they loved, what they liked and what they think could be improved, it's all here to help you make the most of your next trip. Only TripShock! customers may leave reviews. Please login to your reservation to post your review.


Review of Sunset Sail Aboard the Historic When and If

  • Susan Fairbairn USA Jun 18 2019 10:08am

    Verified TripShock! Traveler Review
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  • Rhonda Christie USA about 4 months ago


    This was an incredible experience!! We had the BEST time! The crew was amazing. I would highly recommend this to everyone. PLEASE go on this cruise.

    Verified TripShock! Traveler Review
  • Susan Fairbairn USA about 4 months ago


    Verified TripShock! Traveler Review
  • Jan Meade USA about 5 months ago

    Awesome Sunset

    Schooner was beautiful. The staff was friendly and the sunset was amazing. Seas were a bit rough on our trip, but the crew was attentive offering warm towels and blankets after we got splashed by a few waves.

    Verified TripShock! Traveler Review
  • John Austin USA about 5 months ago


    The captain and crew very knowledgeable and personable. The schooner is beautiful and well maintained. The cheese and nut tray was perfect. The captain made sure that all onboard had a wonderful view of the sunset. A truly enjoyable evening.

    Verified TripShock! Traveler Review
  • Gabriela Espejo Alabama, USA about 5 months ago


    Verified TripShock! Traveler Review
  • Michelle Brumfield USA about 6 months ago


    Awesome boat and crew!! Great stories with the captain! Amazing cheese and crackers with awesome red wine!!! Would definitely book the When and If again!!!!!!

    Verified TripShock! Traveler Review
  • Mitzi Thompson USA about 7 months ago


    Really enjoyed the Sunset Sailing! The crew was fantastic and very informative! Everyone should take this at least once!

    Verified TripShock! Traveler Review
  • Mylene Ramirez USA about 7 months ago


    Great time!!!!

    Verified TripShock! Traveler Review
1-8 of 8
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