UpWind Kiteboarding

Key West, FL
305-432-1355

Upwind Kiteboarding Kiteboarding Trips

Can I kite off the beach in Key West ?


​You can -- but only with a SE to SW wind direction.   But why would you want to kite from a dirty, smelly beach with obstacles in the water? You've spent a lot of money to come to Key West, so why not join us by boat at our world-class kiteboarding location -- clear, clean, shallow water, super flat for miles -- epic ! 


I don't need a lesson -- Why should I choose UpWind Kiteboarding ?

We are the only full-time, professional kiteboarding operation in Key West.  This is our only job and we do it full time, not just part time when it's convenient. 
We have a custom-built boat just for kiteboarding allowing us to reach our shallow-water location.  On board we have a compressor for inflating kites plus 20 new Cabrinha kites in all sizes just in case you need a bigger or smaller kite. We also have many different board sizes available.  We also provide wetsuit, thermal tops, and wind-stopper jackets to our customers if needed.    We absolutely will take care of your every need ! 


How do I book a kiteboard lesson / kiter session ?


During the day we are usually out of reach -- on the water teaching, kiting, SUPing, Scuba diving, snorkeling, or catching monster fish. Our 2018 season begins late-October and runs through mid-May.  For reservations use the "contact us" form. You can also email us :  skot@upwindkiteboarding.com  
or text or WhatsApp us : (305) 432-1355​


How do I pay for kiteboard lessons / kiter sessions ? 

For lessons, we require a $100 deposit at time of booking -- nonrefundable within 5 days of the lesson -- refunded if lesson cancelled by UpWind Kiteboarding.  The $100 will be applied to the balance due after completion of the lesson.   All payments are due after each session.   For payment we accept all major credit cards with instant swipes with SQUARE.  We also accept cash but not checks. 


What if there is no wind during my lesson or kiter trip ? 

Unfortunately the wind doesn't blow every day.  No wind = no cost.   If the wind dies during the session then we will pro-rate the cost. 


Is kiteboarding difficult ? 

It's not hard but it's not easy either.  Taking lessons from a competent instructor will allow you to learn the skills necessary to progress quickly.  Once you learn the basics, progressing is just a matter of practice, practice, practice. 


Where do you teach your lessons ? 

We have a very unique location for teaching. Key West is surrounded by miles of very shallow water. All of our lessons and kiter trips take place far away from any land -- in knee deep water.  Our boat "Solaris" is our office.  

I'm a windsurfer / wakeboarder / surfer, why can't I just get a kite and learn on my own?

You can certainly try -- others have -- but it won't be pretty.   Kiteboarding requires a very unique skill set and can be extremely dangerous to not only yourself but to those around you if you try and learn on your own. Taking lessons from a qualified instructor will greatly reduce the danger factor and the length of time you'll need to become a confident, competent kiter. 

Does kiteboarding require a lot of strength ? 

No. Learning proper kite flying technique and proper body positioning will allow you to kiteboard with very little effort.  Becoming confident as a kite flyer will also allow you to relax and rely on finesse not strength. 


Can a non-kiting passenger join us on the boat ?


We limit our boat load to 10 people including 4 crew. If we have room, non-kiting passengers can join us. Please understand that it is a working boat and not a pleasure cruise. Often times the ride out and back are very rough and very wet. There is no dry land where we go -- the depth ranges from a few inches to 3 feet.  Cost per non-kiting passenger = $20

How much does kiteboarding gear cost ? 

That varies greatly by brand.  We only use Cabrinha kites for our school and rentals.  If interested, we can get you discounted pricing if you are one of our customers.  We are a dealer for the following : Cabrinha kites, boards, and gear, NeilPryde wetsuits and water wear, Imagine SUP boards, JP SUP boards, Mystic, Axis kiteboards, HyperFlex, SPEX goggles, Kiteanchor.    You can also purchase used gear but be aware of any "great" deals -- cheap gear usually means bad gear.  We can give you advice on any gear new or used -- just text or email us.

Q & A


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Frequently asked questions