Set sail on a schooner for a breathtaking sunset trip, with complimentary wine and beer.
Key West, · Water sports
Listing highlights
What you’ll do
This experience is hosted in English and Spanish.
4.96 out of 5 stars, from 266 reviews
4.96, · 266 reviews
0 of 0 items showing
, · May 2026
The sunset sail was a perfect way to end the day. Crew was very friendly. Would do this sail again next time we are in Key West.
Jennifer
Madison, WI
, · May 2026
We absolutely loved our Key West sunset cruise on the “When and If!” The crew was great, and clearly loved what they do. Learning the history of the boat - how it was commissioned by General Patton to sail around the world “when the war is over, and if I live through it” - made the cruise all the more special. We even got to help hoist the sails!
Diana
Chesapeake, VA
, · May 2026
We booked this on a whim when we had a free evening thinking it would be touristy but a quick and easy way to get on the water. It turned out to be the best money we spent on the whole trip. The crew was friendly and knowledgeable, and the sailing was intense enough we had to hang on to the lines with both hands a few times. Not even 30 people on the boat. At less than $150/pp I have to say this is the best value on the island and absolutely something we would do again if we return to Key West.
Lauren
United States
, · May 2026
This was an amazing experience for a first-time visit to the Keys! Would recommend for everyone to do this a least once while in the Keys!
Danielle
Chicago, IL
, · May 2026
Expect a really good time
Laurie
Fargo, ND
, · May 2026
I will be looking forward to do it again in the future
David
Michigan, United States
Upcoming availability
0 of 0 items showing
Where we’ll meet
Key West Bight Marina 202 William St. Key West, FL
Key West, Florida, 33040
About me
Key West captain
I have been sailing these waters for over a decade, giving me outstanding local knowledge of the weather and surrounding waters. I am the owner of four beautiful sailboats, which I charter out to the public for private sailing experiences. My dream of sharing my love of sailing and Key West’s spectacular sea-life and eco-systems is now a reality.
To help protect your payment, always use Airbnb to send money and communicate with hosts.
Things to know
Guest requirements
Guests ages 4 and up can attend.
Activity level
The activity level for this experience is light and the skill level is beginner.
What to bring
A light jacket, You are welcome to bring your own snacks
Cancel at least 1 day before the start time for a full refund.
Water sports with knowledgeable hosts
Water sports are led by surfers, boaters, and other hosts who showcase what makes the city unique.
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No availability
Sail into the sunset
4.96 · 266 reviews
No availability
What you’ll do
This experience is hosted in English and Spanish.
4.96 out of 5 stars, from 266 reviews
4.96, · 266 reviews
0 of 0 items showing
, · May 2026
The sunset sail was a perfect way to end the day. Crew was very friendly. Would do this sail again next time we are in Key West.
Jennifer
Madison, WI
, · May 2026
We absolutely loved our Key West sunset cruise on the “When and If!” The crew was great, and clearly loved what they do. Learning the history of the boat - how it was commissioned by General Patton to sail around the world “when the war is over, and if I live through it” - made the cruise all the more special. We even got to help hoist the sails!
Diana
Chesapeake, VA
, · May 2026
We booked this on a whim when we had a free evening thinking it would be touristy but a quick and easy way to get on the water. It turned out to be the best money we spent on the whole trip. The crew was friendly and knowledgeable, and the sailing was intense enough we had to hang on to the lines with both hands a few times. Not even 30 people on the boat. At less than $150/pp I have to say this is the best value on the island and absolutely something we would do again if we return to Key West.
Lauren
United States
, · May 2026
This was an amazing experience for a first-time visit to the Keys! Would recommend for everyone to do this a least once while in the Keys!
Danielle
Chicago, IL
, · May 2026
Expect a really good time
Laurie
Fargo, ND
, · May 2026
I will be looking forward to do it again in the future
David
Michigan, United States
Upcoming availability
0 of 0 items showing
Where we’ll meet
Key West Bight Marina 202 William St. Key West, FL
Key West, Florida, 33040
About me
Key West captain
I have been sailing these waters for over a decade, giving me outstanding local knowledge of the weather and surrounding waters. I am the owner of four beautiful sailboats, which I charter out to the public for private sailing experiences. My dream of sharing my love of sailing and Key West’s spectacular sea-life and eco-systems is now a reality.
To help protect your payment, always use Airbnb to send money and communicate with hosts.
Sail into the sunset
Set sail on a schooner for a breathtaking sunset trip, with complimentary wine and beer.
Key West, · Water sports
Listing highlights
No availability
Things to know
Guest requirements
Guests ages 4 and up can attend.
Activity level
The activity level for this experience is light and the skill level is beginner.
What to bring
A light jacket, You are welcome to bring your own snacks