Sunset Sail on Historic Schooner Yacht

Key West, United States

Experience hosted by Seth

2 hours, Hosted in English

What you'll do

Experience true classic sailing on Key West’s most elegant and historic schooner for a gorgeous open sunset sail. Our sunset sail includes complimentary wine and beer with optional onboard premium beverage upgrade.

We board 15min prior to departure from the Key West historic seaport at 201 William St. for a 2hr sunset trip which allows guests to help raise sail, take a turn at the helm or relax and enjoy your trip.

Once off the dock, we motor out of the harbor, point the ship into the wind and set sails. Our guests are welcome to lend a hand or sit back and take in the experience of a traditional classic yacht from the best view! Enjoy as the schooner turns with the wind and the engine is turned off! You're sailing now!

Once the sails are up and the crew has adjusted them to the wind, your talented crew will serve up some delicious house wine that even has the When And If on the logo!

We invite you to ask any questions about how the boat operates and what it takes to sail a Schooner. Each one of our crew loves to share their stories of what brought them to the sea. The ship also has her own unique history as the once private yacht built in 1939 for General George Patton, we love to share all that we know about the vessel, as well as local knowledge of Key West waters and ocean-life.

Sailing on the Schooner When And If is an experience not to be forgotten!
Experience true classic sailing on Key West’s most elegant and historic schooner for a gorgeous open sunset sail. Our sunset sail includes complimentary wine and beer with optional onboard premium beverage upgrade.

We board 15min prior to departure from the Key West historic seaport at 201 William St. for a 2hr sunset trip which allows guests to help raise sail, take a turn at the helm or relax and enjoy your trip.

Once of…

What's included

  • Drinks
    Complimentary Schooner wine, beer and bottled water. Or take advantage of o...

Meet your Host, Seth

Host on Airbnb since 2016
  • 141 Reviews
  • Identity verified
Captain Seth Salzmann - A Key West local who has been sailing these waters for over a decade, giving him outstanding local knowledge of the weather and surrounding waters. Once the youngest licensed Captain in the USA, he is now the owner of 4 beautiful sailboats which he charters out to the public for private sailing charters. The dream of sharing his love of sailing as well as Key West's spectacular sea-life and eco-systems is now a reality!
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From $89
/ person
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Where you'll be

We sail out of Key West's historic seaport at 201 William St. Sailing from our downtown Key West location for the 2020-2021 season allows our guest to sail past the famous Mallory square, private and uninhabited islands and take in the spectacle of the world famous Key West sunset from the best seats on the island! Keep an eye looking out over the water as dolphins, sea turtles and rare sea birds are a common sight!

Rated 4.94 out of 5 from 141 reviews.

Ashley
May 2021
This was such a fun and unique experience. It has the perfect vibe we were going for, which was a fun and relaxed sunset cruise without the crazy party vibes, setting it apart from all of the many sunset cruises Key West has to offer. The schooner was stunning and the crew was so friendly. Enjoyed drinking the included wine and watching a beautiful sunset! 10/10 experience, would recommend!
Kevin
May 2021
The Sail Boat experience was outstanding, cruising around Key West and see the sunset at sea. It was my first experience sailing. I was amazed how smooth the sail was in windy, rough waters. It was nice to know the history of the "When and If". I recommend it to everyone of all ages. Next up: Around the world.
Naomi
May 2021
The cruise was great, the sunset beautiful the crew was very good handling the schooner, and interacting with the guests. I highly recommend the sunset cruise.
Hillary
May 2021
This experience was amazing! The crew was so nice and even were super nice and helpful when I got a bit sea sick for a minute. The sunset could not have been more beautiful for the afternoon we went out ! 10/10!
Leigh-Anne
May 2021
This was the highlight of our visit to Key West!!!!!! Very informative crew. We felt safe at all times. It was exhilarating and we look forward to sometime in the future to sail with her again. Truly memorable!!!! We loved the history of the “If and when”. She sailed beautifully!!! We had the most magical experience!! Truly the highlight of our trip.
Jodi
May 2021
This was a fantastic experience! It was a much smaller and more intimate experience than the other area sunset cruises with only maybe 15-20 people on board. It was way better than the other area sunset cruises that were on huge boats and were packed with people and very loud. This was a much better option, very relaxing and a beautiful boat!

Activity advisory

Expert industry partners
We partnered with the Adventure Travel Trade Association, experts in adventure travel, to define best practices and standards for safety.
Know your comfort level
Please note outdoor activities carry risks, and you may be exposed to dangerous situations as part of this experience. Make sure you can participate safely given your abilities and the conditions (such as location, weather, and equipment).

Things to know

Cancellation policy

Any experience can be canceled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

Guest requirements

Up to 10 guests ages 4 and up can attend. Parents may also bring children under 2 years of age.

What to bring

A light jacket

You are welcome to bring your own snacks