Key West Paddle Classic 2027
About This Event
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.
Race Distances
Ready to run?
Registration Pricing
OC-1
$95.00
+ $6.70 processing fee
event_busy Registration closes May 7, 2027
OC-2
$95.00
+ $6.70 processing fee
event_busy Registration closes May 7, 2027
Prone
$95.00
+ $6.70 processing fee
event_busy Registration closes May 7, 2027
SUP 14'
$95.00
+ $6.70 processing fee
event_busy Registration closes May 7, 2027
SUP U-14
$95.00
+ $6.70 processing fee
event_busy Registration closes May 7, 2027
Surfski
$95.00
+ $6.70 processing fee
event_busy Registration closes May 7, 2027
Surfski 2
$95.00
+ $6.70 processing fee
event_busy Registration closes May 7, 2027
Sea Kayak
$95.00
+ $6.70 processing fee
event_busy Registration closes May 7, 2027
SUP 3-Person Relay
$70.00
+ $5.20 processing fee
event_busy Registration closes May 7, 2027
4-Mile SUP 14'
$75.00
+ $5.50 processing fee
event_busy Registration closes May 6, 2027
4-Mile SUP U-14'
$75.00
+ $5.50 processing fee
event_busy Registration closes May 6, 2027
Prices from the official registration page, updated several times a day.
Registration links may earn us a small commission at no extra cost to you.
Weather
Frequently Asked Questions
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Race Day Schedule
5/8/2027 06:00
12 Miles Start
5/8/2027 06:00
12 Miles Start
5/8/2027 06:00
4 Miles Start
5/8/2027 06:00
4 Miles Start
5/8/2027 06:00
12 Miles Start
5/8/2027 06:00
12 Miles Start
5/8/2027 06:00
12 Miles Start
5/8/2027 06:00
12 Miles Start
5/8/2027 06:00
12 Miles Start
5/8/2027 06:00
12 Miles Start
5/8/2027 06:00
12 Miles Start
Registration
Registration links may earn us a small commission at no extra cost to you.
Local Running Store
Key West, Florida Keys
Fit2Run Key West is the Southernmost running store in the United States, located on the iconic Duval Street. Serving Key West's vibrant running community and the many runners who come to train and race in the Florida Keys, from the Key West Half Marathon to the Keys 100.
All Fit2Run locations phone (844) 348-2786 language Visit WebsiteRunner's gear
Gear for race day
ASICS Sonicblast 2 (women's)
Fast-day trainer, new for fall 2026
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ASICS Novablast 5 (men's)
Bouncy trainer for easy days and tempo
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Garmin Forerunner 265
GPS watch with training load and AMOLED screen
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Find More Races
Key West Paddle Classic 2027
May 8, 2027