Key West Paddle Classic 2027 - Surfski 2
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External Event
Distance
12 mi
Pace
All paces
Terrain
Road
Difficulty
All Levels
About this run
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 June 2025 Registration: $75 Pricing will increase $10 per month until race day. HOTEL BOOKING: Room Rates at Blue Flamingo One King or Two Queen Bed: $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. BLUE FLAMINGO LINK Room Rates at Hilton Garden Inn Key West: One King Bed or 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 Fairfield Inn Key West: One King Bed: $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. FAIRFIELD INN LINK Room Rates at Beachside: One Bedroom Suite Resort View $339 Per Night One Bedroom Suite Water View $379 Per Night Three Bedroom Suites $699 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. TO BOOK: Hotel Directly - Call to make their reservations 305-296-8100 use Key West Paddle Classic as the group name Link to Book - Complete the form use Key West Paddle Classic as the group name in the form, they will get a confirmation by email from BRIGHTWILD with in 24 hours. Guests will need to book prior to Monday April 13, 2026 and identify Key West Paddle Board Classic and dates of the event.
Typical conditions
For events around May 2027 in Key West, FL, United States: Typical spring conditions in this region — mornings can still be cool; confirm start-time guidance on the official page.
How to prepare
Half marathon prep usually includes a weekly long run that builds toward 16–20 km, plus easy runs for recovery. Confirm packet pickup and start procedures on the official registration page.
Plan longer races for 2026Getting there
This event is listed in Key West, FL, United States. Confirm the exact start venue, parking, and transit options on the official registration page.
Registration is handled by the official event organizer
Know a local group? Host a community run in Key West
