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Sunset Sail on Historic Schooner Yacht

Key West, United States

Experience hosted by Seth

2 hoursHosted in English
Committed to safety
This host committed to Airbnb’s COVID-19 safety guidelines.
Up to 10 people
Includes drinks

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
  • 116 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
Book for a private group
Fri, Apr 23
$89 per person
$89 per person
Sat, Apr 24
$89 per person
6:30 PM - 8:30 PM
Join 2 other guests
$89 per person
Sun, Apr 25
$89 per person
6:30 PM - 8:30 PM
Join 2 other guests
$89 per person

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 116 reviews.

William
April 2021
A great sunset cruise, even though the weather wasn't the best. The crew was attentive, informative and professional. The yacht was beautiful and smooth sailing. Unlike some other sunset cruises, this allowed us to enjoy the peace and quiet of the sail without music blaring to ruin the moment. Very enjoyable!
A great sunset cruise, even though the weather wasn't the best. The crew was attentive, informative and professional. The yacht was beautiful and smooth sailing. Unlike some other…
Patric
April 2021
The "When and If" is a beautiful ship, the crew was great, and the sunset was awesome. Would do it again in a heartbeat.
Kelly
April 2021
What an absolutely beautiful classic vessel to spend the evening on! We sailed out of the Key West seaport to watch the sunset with her friendly crew and a small group. There was only light wind but it was enough to catch the sails and carry us out fast enough to watch unobstructed as the sun melted into the ocean. That might sound a little overdramatic but it was very cool. However the best part was Seth‘s (and crew’s) willingness to answer our many questions and share his knowledge of sailing and the ocean. Would highly recommend this to anyone… So much better than a party boat!
What an absolutely beautiful classic vessel to spend the evening on! We sailed out of the Key West seaport to watch the sunset with her friendly crew and a small group. There was o…
Sarah
April 2021
This was a fantastic way to spend an evening: wind in my hair, cold beverage, and a beautiful sunset! The crew were fantastic, both at sailing the boat and showing us a good time. If you have never sailed before, this is a great place to start.
This was a fantastic way to spend an evening: wind in my hair, cold beverage, and a beautiful sunset! The crew were fantastic, both at sailing the boat and showing us a good time.…
Catherine
April 2021
I totally enjoyed the experience. Make sure you bring water proof jacket. It gets chilly and depending where you’re sitting, you can get wet! It was a blast.
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!

Choose from available dates

Book for a private group
10 available
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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