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Kiteboarding in the Florida Keys is some of the best flat-water riding in the entire country. Through Islamorada, Marathon and Key West, the small chain of islands are connected with an intertwining web of sandbars and ‘flats,’ the knee deep playgrounds for Florida Keys kiteboarders. The consistent wind and shallow, clear, warm water is ideal for learning to kiteboard, whether its your first kiteboarding lesson or that last guided session you need to make you an independent rider.

"I’m a business owner so I tend to be very picky when I pay for other services... I have got to say it was hands down VIP service! Every instructor was amazingly helpful and you could tell they wanted to be there. The next day I went to the cable park to learn to foil and I had the same experience at the park as I did the water. Then... when I went to the retail shop I was a kid in a candy shop...such a great selection. I highly recommend Otherside for lessons, the sitter session, cable park and the retail shop for all your gear."

" I have been kiteboarding on and off for 3 years - mostly on vacation internationally and in south florida (Miami). Since I am always in new locations I have had a bunch of lessons and supervised sessions. Mike was BY FAR the best instructor I have ever had (and this wasn't even a lesson!). He was so helpful and gave amazing tips on equipment, technique, and kite spots in the area. Aside from the great customer service and instruction, the kite spot was so beautiful! It was flat, warm, clear and shallow - not to mention we were the only people there. Literally perfect learning conditions! If you are in South Florida and considering learning how to Kiteboard, I definitely recommend making the drive to Islamorada and doing it with Mike - the value for money compared to other kite schools in SFLA is hands down the best. Overall, Otherside, Mike and the kite spot exceeded my expectations by far - definitely worth the drive from Miami. Can't wait to come back!!"

"Mike, the owner, makes kiteboarding simple. Completely different than other kiteboarding instructors. He was one of the innovators of the sport! I could already board, but wasn't good. Mike slows it down and shows how it should be relatively effortless. Best kiteboard instructor I have ever seen. Plus, the area is beautiful. Can't wait to get back there!"

oTHErside’s Kiteboarding Lessons & Sessions

Sessions run daily (wind dependent) at 9am and 1:30pm for approximately 3 hours. Our windy season typically runs from October-May.

We shuttle by boat to an exclusive flat that provides ideal learning conditions; lots of shallow water and very little kite traffic.

BEGINNER COURSE - Wind theory, wind-window, set-up, safety, launching, landing, kite control, water relaunch, self-rescue and board skills.
--$425 for one-on-one instruction.
--$525 lesson for two. Participants must be within 40lb of each other to share a lesson. 1 instructor, 1 set of gear to share.

PRIVATE INTERMEDIATE/ADVANCED - What do you need to work on? Private instruction to pick up where you left off. 

SITTER SESSION For intermediate riders that just need a few pointers. Riders must be able to stay upwind to qualify for this option. This is not a private lesson. Your instructor will be kiting with you. Their objective is to ‘keep an eye’- To be there if help is needed, act as a guide, or offer tips to enhance your riding experience.
--Our gear- $225.
--Your gear- $189.
Disclaimer: If a sitter session turns into a lesson, based on the instructor's discretion and their comfort level with your kiteboarding skills, the full $425 lesson rate will be applicable.

BOAT TRIP (subject to seasonal availability) - For riders who are 100% self-sufficient. Otherside will assist in rigging, launch and land only.
--$100. 2 person
minimum for the boat to leave the dock.

PRIVATE BOAT- Looking for a more intimate experience for your group? Rates include up to two instructors/gear sets. 6 passengers max.
--$1100 half day (3 hours) or $1699 full day (7.5 hours)  

OFFSITE INSTRUCTION- Want to take your instructor to your home beach? To your vacation spot? Enjoy the oTHErside experience anywhere you'd like! Minimum two days of lessons plus one day of paid travel.
--$750/day plus travel expense and two meals per day. $850 for Mike.

CANCELLATION POLICY - When booking a kiteboarding lesson, or to reserve a spot on a boat trip, credit card info will be taken as a security deposit. The card will not be charged until after the lesson, or not at all if you choose to pay cash. In the event that there is no wind, or unfavorable conditions and oTHErside cancels the booking, no fee will be charged. All other reservations must be cancelled 24hrs in advance. No-show reservations will be charged in full, as our instructor have allocated their time, and missed an opportunity to teach another student. Lessons cancelled with less than one days notice will be charged 1/2 off the appropriate lesson fee.

In the unfortunate event that the wind doesn't cooperate, we'd still love to get you out on the water!

Sandbar Chillin

Keys Cable Wakeboard Park



Spearfishing and Freediving

Paddle Excursions

Florida Keys Public Kite Launches:
Annes Beach ENE- SW
Curry Hammock State Park- ENE-SSW
Founders Park NW
CoCo Plum ENE-SW
Sombrero S-SW