EXPERIENCES
Discover the beauty of the ocean with the Florida Keys Watermans Company. We invite you to join us for one of our upcoming experience camps, where you'll have the opportunity to explore the vast wonders of the ocean by kitesurfing, wingfoiling, paddleboarding, outrigger canoeing, fishing, or e-foiling.
BACKCOUNTRY EXCURSIONS
Embark on a thrilling Backcountry Florida Keys or Bahamas Expedition and discover the hidden gems of this tropical paradise! This exclusive adventure takes you off the beaten path and into the heart of untouched wilderness for kitesurfing, wingfoiling, fishing, paddling, and more. Guided by seasoned explorers, you'll navigate pristine waters, explore remote islands, and encounter an array of wildlife in their natural habitat.
GUIDED DOWNWINDERS
Enjoy a stress free ride to Cocoa Plum or Curry Hammock knowing our shuttle will be waiting with an ice cold beverage to transport you back to Grassy Flats. Services available for advanced paddleboarders, outrigger canoers, kiteboarders, and wingfoilers. 5 riders per trip.
$200 WITHOUT INSTRUCTION
$300 WITH INSTRUCTION
DECEMBER 7 - 21
DOWNWINDAPALOOZA
Calling all kiters and windsurfers! Embark on an epic 60 mile downwinder from Grassy Key to Key West. Not feeling the whole 60 miler? No problem, go for our 20 mile division to Veterans Park! Wind window is from December 7th to the 21st.
Entry fee includes boat support, transportation, welcome cocktail party, after party, clinics, and more!
JANUARY 2026
WOMEN OF WING CLINIC
Join us for a long weekend of amazing adventures, laughter, friendship. Newbies welcomed to come and learn what this sport is all about, instruction additions available. For all others come test gear, participate in clinics, have a cable park session, ride the beautiful keys waters, get footage of you and your friends. After a day on the water, enjoy a Grassy Flats Dinner, a sunset cruise, relaxing and reminiscing on the memories.
MAY 2026
Key West Paddle Classic
May 9, 2026 join paddling enthusiasts for a 12-mile elite race around Key West island.
Join Florida Keys Watermans Company in another year of hosting the Key West Paddle Classic! The event has a long history, originating in 1997 under the direction of Micheal O'Shaunessy, and is celebrating its 29th year in 2026!
If you have been a regular and racing the event for years, we thank you! If it is on your race ‘bucket’ list, well my friends, THIS IS YOUR YEAR!
