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Key West · Florida · United States
Shared Sunset Sail on When and If Schooner
Starting From
From $117.18 per person
Current Project Expedition rate
Experience inventory, live availability and secure booking provided by
Project Expedition
The Experience
What your day looks like
With room for up to 28 people to enjoy the gorgeous Key West sunset, the antique schooner yacht When And If is the most elegant sunset sail in town. Take in the unobstructed view in the peace and calm of blue-ocean sailing, with a delicious shared cheese platter and all your new friends!
At a Glance
The experience, in brief
- Take in the sunset without the crowds with a private charter
- Relax and enjoy the peace and calm of ocean sailing
Detailed Itinerary
The journey, in full
Step aboard our historic yacht built for General George Patton. Sit back and relax as we cast off the dock lines and motor out into the harbor, lend a hand or watch the crew hard at work setting sail. Once the sails are up, the engine is turned off and the wind is our propulsion. Take in the sights of Key West from the water as the captain and crew introduce themselves and share their passion for sailing and Key West to our guests. Our trips include boutique wine and select beers as well as bottled water and flavored seltzers
Your Itinerary
Your day, step by step
Day 1
Key West
Boating.
Before You Go
What to know before booking
Meeting & Pickup
202 William St, Key West, FL 33040
Languages Offered
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Planning Notes
Hotel pickup offered: Yes Confirmation: Automatic
Traveler Impressions
What travelers are saying
2026-05-13
5.00 / 5
The captain and crew were amazing! We were given the wrong meeting point on our voucher from PE. The captain called and told me of the error just as we arrived at the wrong place. I told him we would be going back to the hotel to get a shuttle. Once we arrived at the Seaport, he called again to guide me to the ship. The experience on the ship was fantastic and a highlight of our trip to Key West. The crew asked us to help raise the sails and the sailing experience was glorious as we sipped our wine (and beer) and watched the sun set into the sea. An awesome experience which made up for the confusion at the beginning. I would highly recommend Sunset Sail Key West!!!
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