Get clear answers to your most common concerns.
You can—but only with a SE to SW wind direction. You've spent a lot of money to come to Key West, so why not join UpWind Kiteboarding by boat, 5 miles out, at our world-class kiteboarding location—clear, clean, shallow water, super flat for miles—epic!
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. UpWind Kiteboarding provides booties, wetsuits, thermal tops, and wind-stopper jackets to our customers if needed. We absolutely will take care of your every need!
During the day, we are usually out of reach—on the water teaching, kiting, foiling, SUPing, scuba diving, or snorkeling. For reservations, send us a text or WhatsApp—see "Contact Us."
Females and males: You will need to wear medium- to long-length board shorts. We use new-technology, very comfortable seat harnesses with leg straps.
We provide booties, goggles, thermal tops—and if needed: wetsuits, wind jackets, and thermal hats.
For lessons, we require a $200 deposit at the time of booking—nonrefundable within 7 days of the lesson—refunded if the lesson is canceled by UpWind Kiteboarding. The $200 deposit will be applied to the balance due after completion of the lesson.
Full payment is due in advance for experienced kiter sessions—nonrefundable within 7 days of the session, refunded if the session is canceled by UpWind Kiteboarding.
Lesson balances will be collected after each session once we return to the dock. We accept Venmo and all major credit cards with instant swipes via SQUARE. We also accept cash, Apple Pay, Android Pay, and Zelle.
Unfortunately, the wind doesn’t blow every day. No wind = no cost. If the wind dies during the session, we will pro-rate the cost.
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.
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, 6 miles out—in knee-deep water. Our boat is our office.
You can certainly try—others have—but it won’t be pretty. Kiteboarding requires a very unique skill set and can be extremely dangerous, not only to yourself but to those around you if you try to learn on your own. Taking lessons from a qualified instructor will greatly reduce the danger factor and the length of time needed to become a confident, competent kiter.
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.
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, not a pleasure cruise. Often, the ride out and back is 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: $50
Costs vary greatly by brand. UpWind Kiteboarding only uses Cabrinha kites for our school and rentals. If interested, we can get you discounted pricing as one of our customers.
We are a dealer for the following: Cabrinha kites, boards, and gear; Dakine wetsuits and waterwear; HyperFlex; Skot Harness; Skot sun mask; AKTIV goggles; and Kiteanchor.