Key West Paddle Classic 2027
Key West Paddle Classic 2027 is a paddle race on May 8, 2027 in Key West, FL, with an entry fee of $75.
- Date
- May 8, 2027 (289 days to go)
- Price
- $75
- Sport
- Paddle
From the Organizer
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.
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.
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.
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.
Events
Weather
Typical Conditions
It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.
Typical High
85°
Typical Low
73°
Chance of Rain
24%
Based on US Climate Normals data from Key W Wfo.
Host City
About Key West, FL
Population
25,824
as of 2023
City Elevation
3 ft
Nearest Airport
EYW
Key West International Airport · 1 mi
Major Hub
MIA
Miami International Airport · 127 mi
Time Zone
Eastern Time
From Endurance Grid
A mid-size host city. Enough lodging and amenities to keep race weekend easy, without big-city sprawl.
Race Location
Your Next Start Line
What Are You
Waiting For?
Every finish line starts with a single decision. Claim your spot at Key West Paddle Classic 2027, put it on the calendar, and turn “someday” into a start date.
289
Days to train
- Race
- Key West Paddle Classic 2027
- Date
- May 8, 2027
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From Endurance Grid
About This Sport
Endurance Grid is here to help you understand the sport, decide if it’s the right fit, and learn how to prepare. For course distances, logistics, and race-day specifics, always defer to the race organizer’s event page.
Paddle sports cover kayak, canoe, SUP, and outrigger racing on rivers, lakes, and open ocean — from short sprints to marathon distances, split by craft. The water and the weather are as much a part of the race as the field.
It's a full-body, low-impact way to race, where reading the water and a smooth, repeatable stroke matter as much as raw power.
Paddle Sports
Kayak, canoe, SUP, and outrigger races on rivers, lakes, and ocean. Sprints to marathon distances, split by craft.
Coming Up
More Paddle races near Key West, FL
Sandy Springs SUP Showdown
From $75 · 200 Morgan Falls Overlook Park
669 miles away
Take the Lake
5K · 10K · Under 25 mi · From $10 · Lake Waccamaw
704 miles away
FOR LOVE OF WATER (FLOW) SSI 26
From $60 · 15th Street Gould's Inlet
462 miles away
Paddle for Troops Competitive & Fun SUP Race
From $25 · Sears Landing Boat Dock and Grill
732 miles away
Plan your trip
Make it a Racecation
Coming from out of town? There's more to Key West than race day. We'll help you line up nearby lodging, flights, a rental car, and things to do so you can make the most of your racecation.
Plan your trip to Key WestFrequently Asked Questions (FAQs)
What is the Key West Paddle Classic 2027?+
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Key West Paddle Classic 2027
May 8, 2027