Private Key West Sunset Sail

This sail was fantastic, staff was very knowledgeable and accommodating. We took 25 family members, staying at the Perry Hotel on Stock Island for a wedding and everyone raved about this sail. Sailboat was very cool and history was interesting. Would do it again in a heartbeat!

The experience was truly amazing. Despite it being in harsh weather, the crew managed to make the best of the situation. It was also interactive and we got to set the sails. You got to talk to the crew one on one and really interact with them as a person. There was tons of beverages and even a cheese plate. One the the crew members named Koss was really amazing, she was able to interact while also preforming her job. She was able to keep the mood light despite the weather being not so light. She made us feel involved and engaged.

We had a great sail with Captain Will and First Mate Cameron. Because the day had gusts up to 26 mph we had great sailing on a wonderful boat. Plan to do it again!

We set sail for my brother’s 40th birthday on a sunset cruise, and it could not have been more perfect. The boat itself was absolutely beautiful—clean, comfortable, and clearly well cared for. From the moment we stepped aboard, the captain and first mate made us feel welcome. They were incredibly knowledgeable, genuinely kind, and effortlessly friendly, sharing great insights while keeping the experience relaxed and fun. The sunset was stunning, the ride was smooth, and the entire trip felt both special and seamless. A huge bonus was the convenience—they picked us up directly at Sunset Key and dropped us off in Key West, which made the evening completely stress-free. An unforgettable experience from start to finish. 5/5 stars, and I would absolutely recommend this cruise to anyone looking for a memorable time on the water.

Pretty boat high end services, even an opera singer. This boat has it all. Small and intimate. Had a birthday sail, which didn’t disappoint. Loads of rain , a waterspout, and an amazing sunset.

Absolutely incredible experience aboard Malabar X. The whole process was really great booking was easy, we then had to move the sail and Sunset Sail Key West was so accommodating and made the switch easy. The sail was just fantastic, the crew was knowledgeable and able. Most importantly the beer was cold. Would return every month if I could. If you are going to Key West, you must sail with these folks.

Amazing experience I highly recommend using this company if your looking for a cruise in the keys. The crew was great and very informative about the keys and the price was great.

Had a lovely time out on the water off the historic Key West port, aboard the 33 foot High Tide. Harley and Casey were wonderful hosts, and were very knowledgable about the local waters. We were provided with plenty of ice, water, and soft drinks during our sunset sail, and thoroughly enjoyed our time under sail. The cheese platter was a nice little nosh while taking in the scenery. Thanks again for all your skill and hospitality!

We took our grandmother on a sunset sailing for her 85th Birthday. We were on High Tide with Harley and Casey. They made the trip so wonderful. We all had an amazing time. And that was due to them. They made sure we saw the sunset perfectly. Truly a wonderful experience. We would highly recommend this sailing to anyone!

I wanted a sail that was just that, a sail, not a booze cruise or snorkel or sunset sail. They gave me exactly what I was looking for. We spent 4 hours cruising in 12 to 15 knot winds on a beautiful day. The crew, Logan and Hannah were an absolute delight and allowed me to help work and sail the boat a Glander 33. The website wasn’t very clear about what they provided in terms of snacks and liquids but that wasn’t the fault of the crew. The only recommendation I have is that it is time for a new set of sails.