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
NOVEMBER 28 - DECEMBER 20, 2026
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 November 28 - December 20th
Entry fee includes boat support, transportation, welcome cocktail party, after party, clinics, and more!
MAY 2027
30th Anniversary
Key West Paddle Classic
Welcome to the 30th Annual Key West Paddle Classic!
As a Favorite Destination Race, we offer one of the largest paddle categories on the East Coast! The Key West Paddle Classic is officially ON for May 8th, 2027!
We’re excited to announce our new partnership with: Blue Flamingo Hotel. The event will be hosted start and finish right here at Beachside and official after parties at Blue Flamingo Hotel! New location, same awesome race. This one’s going to be epic.
If you have been a regular and racing the event for years, we thank you for coming back! If it is on your race ‘bucket’ list, well my friends, THIS IS YOUR YEAR!
