Sip fine wines and craft beers on an intimate schooner sail as the sun sets off Key West’s coastline
4.9 stars• 5.7K reviews
From$147/ personincl. taxes and fees
Duration
2 hrs
Includes
Wine and beer, Hors d'oeuvres
Highlights
Toast the day’s end aboard a historic schooner sailing past Stock Island and Key West. Sip curated wines and premium beers while enjoying gourmet hors d'oeuvres as the sky shifts to sunset hues.
Sail aboard a classic Key West schooner
Sample eight hand-selected wines from around the world
Savor imported and domestic craft beers
Nibble on charcuterie, cheeses, fruit and chocolate
Watch a vibrant sunset during a relaxing 2-hour cruise
What's Included
Eight varieties of wine
Premium imported and domestic beers
Charcuterie boards, fruit and chocolate
Sodas and bottled water
Things to Know
Guests must be at least 13 years old. Bring a valid photo ID if you plan to consume alcohol.
Cancellation Policy
All ticket sales are final and non-refundable. Rebooking within 24 hours of your scheduled time is subject to availability and will incur a $30 fee.
FAQs
Bring sunglasses, a camera, photo ID, and during cooler months a sweatshirt or light jacket.
This sail is intimate, relaxed boutique sailing experience (on a historic schooner) rather than a large party boat.
Yes. Free parking is available at the marina. Choose the second parking lot to the left, past The Perry Hotel.
Meeting details
The Perry Hotel & Marina - Slip J5, 7011 Shrimp Road, Key West
Key West sailing doesn't get much better than this, according to travelers who consistently rave about their time on the water here. Whether you're booking the adventure combo with snorkeling and kayaking through the mangroves or opting for the more leisurely sunset wine cruise, you're apparently in for something special. The crew members get called out by name again and again, with captains like Mary, Janet, Anthony, and Micah earning particular praise for being knowledgeable, professional, and genuinely fun to be around. People love that these aren't massive cattle-call operations. Groups tend to max out around 16 passengers, which creates an intimate vibe where the crew can actually give you personal attention and fellow travelers become part of the experience rather than just anonymous faces.
The full-day excursions seem to be the showstoppers. You're looking at snorkeling (though not on a reef, so temper expectations accordingly), kayaking around mangrove islands with solid ecology commentary, plus snacks and unlimited drinks throughout. One couple said it was the best day of a rough year, which speaks volumes. The sunset sails hit differently too, with proper wine flights paired with cheese and appetizers, all enjoyed under actual sail power. A few practical notes: the snacks are described as good but light, so consider bringing extra food if you're prone to getting hungry. Weather can look sketchy before departure but often clears up, and you might even spot manatees at the dock. Multiple repeat customers say this is their go-to charter year after year, which tells you everything about consistency.
What people are saying
Review 1 of 4
5/5
It has been an absolute pleasure and fun experience to sail with Danger Carters. My wife and I had a same-day trip from Miami to Key West to experience some natural and wild experiences and we found Danger Charters on another platform page. Listing seemed like they had decent price for a lot of different activities that we can do within short amount of time. We booked the PM tour, where they advertised about being able to see the sunset on the sail back, without hesitation. The package included unlimited water, sodas, wines and snacks. Activities included kayaking, snorkeling, and sailing within a 5-6 hours window.
And, it turns out that we had much more fun and unforgettable memories during the tour.
Captain welcomed us at the meeting point and went over some safety measures with two of her amazing sail crew members, before we sailed out. We did the kayaking first, where we teamed up in two groups, following one crew per group, exploring around a small island of mangroves where you could witness the wildness and natural habitats of different kinds of sea animals. It was mind blowing to watch some turtles, fish, and stingray going under our boats where everything was maintained safely and naturally. We kayaked for over an hour to two and returned to our boat.
Then, we headed to a snorkeling point. As snorkeling maniacs, my wife and I were a bit disappointed at first by how less of sea animals we could capture under the water compared to some other past snorkeling activities we did at Catalina Islands and Hawaii, but it was a super fun, immersive experience where the water was so clear to see through and spot interesting sea creatures that our crew members dived into show us around. My wife and I had total freedom to browse through the water, where we actually had more entertainment and fun to enjoy our snorkeling independently within the safe areas. We snorkeled about the same amount of time as kayaking.
The best part for us what we could witness on the way back. First, as soon as the snorkeling was over, the crews provided us with unlimited wine and beer selections along with some tortilla chips all of which refreshed bodies and resolved our hunger after doing the activities. Then, we sailed our way back for almost 2-3 hours, having a complete blast and fun with all the other passengers and crews talking about life and different topics (we had about 9 other passengers to boat with). Time flew up to a point where the captain and crews started releasing the sailclothes and sailing without the motor, which to me was a first experience that really blew me away. Everything was quiet, we just hear each other and as the time neared the sunset hour, we had the most beautiful scenery ahead of us with all the tranquil waters and some dolphins jumping in and out in between the sun and our boat. It's hard to describe how magnificent and joyous the experience was, but all I can say is we had a great great great time.
Not to mention, all this experience was impossible without the captain and her crews on board. From the moment we began our journey, the crews cared about our safety all the time, worrying about our hydration more than anything. All the history and guide information that they provided to us added more depth to the tour. And, all the young, kind, and passionate crew members approached us with care, warmheartedness, and friendliness.
I would definitely recommend ANYONE going to Key West to have a sailing experience with Danger Charters. They are awesome, and I guarantee you will have an unforgettable tour with Danger Charters.
I will definitely revisit Danger Charters again if I happen to make another trip to Key West!
Until next time!!!!
JunLA
May 22, 2026
Review 1 of 1
5/5
It has been an absolute pleasure and fun experience to sail with Danger Carters. My wife and I had a same-day trip from Miami to Key West to experience some natural and wild experiences and we found Danger Charters on another platform page. Listing seemed like they had decent price for a lot of different activities that we can do within short amount of time. We booked the PM tour, where they advertised about being able to see the sunset on the sail back, without hesitation. The package included unlimited water, sodas, wines and snacks. Activities included kayaking, snorkeling, and sailing within a 5-6 hours window.
And, it turns out that we had much more fun and unforgettable memories during the tour.
Captain welcomed us at the meeting point and went over some safety measures with two of her amazing sail crew members, before we sailed out. We did the kayaking first, where we teamed up in two groups, following one crew per group, exploring around a small island of mangroves where you could witness the wildness and natural habitats of different kinds of sea animals. It was mind blowing to watch some turtles, fish, and stingray going under our boats where everything was maintained safely and naturally. We kayaked for over an hour to two and returned to our boat.
Then, we headed to a snorkeling point. As snorkeling maniacs, my wife and I were a bit disappointed at first by how less of sea animals we could capture under the water compared to some other past snorkeling activities we did at Catalina Islands and Hawaii, but it was a super fun, immersive experience where the water was so clear to see through and spot interesting sea creatures that our crew members dived into show us around. My wife and I had total freedom to browse through the water, where we actually had more entertainment and fun to enjoy our snorkeling independently within the safe areas. We snorkeled about the same amount of time as kayaking.
The best part for us what we could witness on the way back. First, as soon as the snorkeling was over, the crews provided us with unlimited wine and beer selections along with some tortilla chips all of which refreshed bodies and resolved our hunger after doing the activities. Then, we sailed our way back for almost 2-3 hours, having a complete blast and fun with all the other passengers and crews talking about life and different topics (we had about 9 other passengers to boat with). Time flew up to a point where the captain and crews started releasing the sailclothes and sailing without the motor, which to me was a first experience that really blew me away. Everything was quiet, we just hear each other and as the time neared the sunset hour, we had the most beautiful scenery ahead of us with all the tranquil waters and some dolphins jumping in and out in between the sun and our boat. It's hard to describe how magnificent and joyous the experience was, but all I can say is we had a great great great time.
Not to mention, all this experience was impossible without the captain and her crews on board. From the moment we began our journey, the crews cared about our safety all the time, worrying about our hydration more than anything. All the history and guide information that they provided to us added more depth to the tour. And, all the young, kind, and passionate crew members approached us with care, warmheartedness, and friendliness.
I would definitely recommend ANYONE going to Key West to have a sailing experience with Danger Charters. They are awesome, and I guarantee you will have an unforgettable tour with Danger Charters.
I will definitely revisit Danger Charters again if I happen to make another trip to Key West!
Until next time!!!!
