Keys Boat Tours

Hands-On Sailboat Lesson

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This is the only sailing lesson outside of Key West. You raise sails, take the helm, switch the lee boards, tack, jibe, and ...learn to sail. I often hear people say "I always wanted to learn how to sail". Pair it with a stay at Parmer's Resort. One lesson is $325. Three lessons, just $750.

100% Hands-On Sailing Lesson

We are the only sailing school outside of Key West. Three hours is the perfect amount of time for a sailing lesson. You leave with a booklet, so to better understand wind direction and points of sail. The rest is hands on; you raise sails, take the helm, switch the lee boards, tack, jibe, and … learn to sail. This lesson makes a great gift. We also offer sailing tours and expeditions a la Outward Bound. Gift certificates available.


 Lesson Rate $325 Price for 1-2 people person for 3 hours
Extra Time +$75 Per hour



Sailing Cruise
We will hoist the sail and go on our way. Fishing, snorkeling, swimming are all on the table. Whatever you want to do!
Sailing Lessons
Here we learn how to understand the wind, and how to use it. We have diagrams for you for wind direction and points of sail. In this 3 hour class, you will learn all there is about; motoring into the wind, anchoring, raising the sail, steering, tacking, and basic navigation. The more adventurous student might want to take the overnight or multi-night sailing expedition. You will depart a novice, and return a seasoned sailor. Our sailboat, Freedom, is a 2003 21' Nimble Bay Hen gaff rigged cat boat with a Yamaha 4hp four stroke outboard.


  • Sunscreen
  • Water
  • Ice Chest

Not Included

  • Lunch and snacks

Things you might want to bring along

Sunglasses, towel, hat, sunscreen, water bottle, wet shoes, neck bib, long sleeve shirt, wind breaker, bandana, wet bag, binoculars,  camera, snacks.


  • A signed release waiver, and cash or credit card payment is required prior to boarding.
  • If prone to seasickness, we recommend that you take Dramamine (or other) the night before.
  • We want you to drink plenty of water, have something to eat, and use sunscreen liberally.



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  • Captain Brian took me for the most spectacular backcountry tour, and he didn’t even know it!

    FRED (the frog) FROM BIG PINE KEY
  • The water was crystal clear, the sea life magnificent, the pelicans close, the Captain gracious, and the sunset backdrop breathtaking!  I cannot recommend this experience any higher!  Bon voyage!

  • I recommend the motor boat / paddleboard combo tour thoroughly. It was our first time on paddle boards and Captain Brian made it so easy.

    sup paddleboard rental keys getaway SARAH FROM TEXAS
  • Thanks so much for customizing our boat trip to serve both our needs!

    kayak florida keys JANINA & CHRIS
  • The protected cove, the rays, the sunset – a perfect outing with Capt Brian. Highly recommended.

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