The Best Sailboat Rentals in Key West

Recent Reviews in Key West

- TL
  Tony
  
  Captained 42' Sailing Catamaran with 3 cabins and all the toys
  One of the better charters I've done. Aaron was responsive before the trip, the boat was in excellent shape, and he made the whole day effortless — no stress, no surprises. If you're deciding, book it. Five stars.
- BC
  Bryan
  
  Captained 42' Sailing Catamaran with 3 cabins and all the toys
  Aaron was super fun and extremely knowledgeable. Our group of five has so much fun sailing the rougher, windier seas. We then made for a secluded spot to fish and swim while we waited for sunset. It was a glorious view and truly checked off a bucket list item for me. Bryan - Oregon
- Brandon
  
  Captained 42' Sailing Catamaran with 3 cabins and all the toys
  Highly recommended Captain Aaron and his crew Brook... they did an amazing job of hosting and tending to our wants. Very nice boat with ample toys and things to do on the water. Will definitely join them again. ⭐️⭐️⭐️⭐️⭐️
- CD
  Carina
  
  33ft The Key West's Most Versatile Sailboat! (With Captain Only)
  Sunset Cruise was responsive throughout the entire process & more than accommodating. Both Eric & Mark were with us through our experience & were nothing but pleasurable and made the day great. I highly recommend Sunset cruise & this boat !
- Bobby
  
  33ft The Key West's Most Versatile Sailboat! (With Captain Only)
  Great owner and communications the captain Nate and first Mate Mark were wonderful , would highly recommend Hightide for a nice sail or snorkeling
- JF
  Jessica
  
  33ft The Key West's Most Versatile Sailboat! (With Captain Only)
  We spent four hours as a family together - it was a great adventure. I highly recommend this experience!