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Sunset Sail on Historic Schooner Yacht

Key West, United States

Experience hosted by Seth

2 hours
Includes drinks
Up to 10 people
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…

Seth's commitment to safety

This host committed to Airbnb’s COVID-19-related safety and cleaning guidelines—including adhering to social distancing guidelines, practicing good hygiene, and ensuring that all participants wear a mask.
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What's included

  • Drinks
    Complimentary Schooner wine, beer and bottled water. Or take advantage of o...
From $89
/ person
Mon, Apr 12
$89 per person
6:30 PM - 8:30 PM
Join 2 other guests
$89 per person
Wed, Apr 14
$89 per person
6:30 PM - 8:30 PM
Join 2 other guests
$89 per person
Thu, Apr 15
$89 per person
6:30 PM - 8:30 PM
Join 2 other guests
$89 per person

Meet your host, Seth

Host on Airbnb since 2016
  • 109 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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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!
Jacob
March 2021
Captain Jack is great, but his crew mates Sydney and Wilson really make the trip! They were all so knowledgeable and friendly, and they knew the answers to all of our questions. We definitely had fun on this trip, and we will be back!
Robert
February 2021
This was a fantastic experience on General Patton’s boat! I hope you are able to sail around the world someday. I’ll be looking for you in Salem this summer.
Erin
February 2021
Great beer selections, something for everyone! Wine was local and delicious. Crew was hilarious and smart. We learned so much a d also had a great time! Just the right amount of people. Absolutely gorgeous boat and perfect night for sailing. Kelsey Wilson and Harley were top notch!!
Great beer selections, something for everyone! Wine was local and delicious. Crew was hilarious and smart. We learned so much a d also had a great time! Just the right amount of pe…
Sarah
February 2021
The Sunset Sail on the When & If was by far our favorite activity while visiting Key West. We were a group of 6 and sat at the wheel with the captain, Kayla. Kayla was extremely knowledgable and friendly, answering all of our questions and laughing along with us. We went for the sunset sail, but learned a lot as well! The crew was equally as friendly. The entire experience was outstanding! The sail is so much better than other sunset cruises that are offered. We enjoyed the quite, non-motor cruising and the sunset experience.
The Sunset Sail on the When & If was by far our favorite activity while visiting Key West. We were a group of 6 and sat at the wheel with the captain, Kayla. Kayla was extremely kn…
Edward
February 2021
When in Key West be sure to make a reservation with Captain Seth on the “One Ans If” . The Crew are super friendly and VERY knowledgeable about the Keys and the vessel! The evening is fun and features drinks while sailing! The most beautiful views of the sunset!
When in Key West be sure to make a reservation with Captain Seth on the “One Ans If” . The Crew are super friendly and VERY knowledgeable about the Keys and the vessel! The evening…
Anne
February 2021
Seth and his crew were great hosts and impressive sailors! Our group had a mix of people who have sailed across the the Atlantic, and some who have never been on a sailboat before. We all had an amazing time. We met new friends, took fabulous pics, and enjoyed a perfect sunset!
Seth and his crew were great hosts and impressive sailors! Our group had a mix of people who have sailed across the the Atlantic, and some who have never been on a sailboat before.…

Choose from available dates

10 available
1 / 2
  • Mon, Apr 12
    6:30 PM - 8:30 PM
    Join 2 other guests
    $89 per person
  • Wed, Apr 14
    6:30 PM - 8:30 PM
    Join 2 other guests
    $89 per person
  • Thu, Apr 15
    6:30 PM - 8:30 PM
    Join 2 other guests
    $89 per person
  • Sat, Apr 17
    6:30 PM - 8:30 PM
    Join 4 other guests
    $89 per person
  • Sun, Apr 18
    6:30 PM - 8:30 PM
    Join 4 other guests
    $89 per person
  • Mon, Apr 19
    6:30 PM - 8:30 PM
    Join 2 other guests
    $89 per person
  • Tue, Apr 20
    6:30 PM - 8:30 PM
    $89 per person
  • Wed, Apr 21
    6:30 PM - 8:30 PM
    $89 per person

Activity advisory

Expert industry partners
Every adventure follows industry guidelines. We partnered with the Adventure Travel Trade Association, expert leaders 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