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! Regis
Hotels Near This Race
Find accommodation close to the start line in Key West, FL. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
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Race Travel Insurance
Don't forget travel insurance for May 8.
You've trained for months and booked a trip to Key West, FL.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
