Key West Paddle Classic 2027

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: Beachside Resort & Residences + 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. Join Florida Keys Watermans Company as we celebrate taking over as hosts of 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! Lazy Dogs hosted the event from 2013-2024 and graciously passed the torch to us for this year! 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! Registration is now open via RunSignUp. Expect nothing different! An affordable race, a challenging course, and great stories of our paddle experience together on the water! RACE INFO - Follow us HERE for updates! https://www.facebook.com/KeyWestClassic/ DATE: MAY 8, 2027 FEES ARE NON-REFUNDABLE - Please plan accordingly. PRICING: May 2025 Registration: $65 Pricing will increase $10 per month until race day. HOTEL BOOKING: Room Rates at Blue Flamingo ONE KING BED: $229 PER NIGHT Rates do not include current city and state taxes totaling 12.5%. Tax rates are subject to change at any time based on government regulation. BLUE FLAMINGO LINK Room Rates at Hilton Garden Inn Key West: TWO QUEEN BEDS: $249 PER NIGHT Rates do not include current city and state taxes totaling 12.5%. Tax rates are subject to change at any time based on government regulation. HILTON GARDEN LINK Room Rates at Beachside: Standard Rooms $239 Per Night One Bedroom Suite Resort View $339 Per Night One Bedroom Su