The Key West Paddle Classic 2027 is a paddle sports event offering 12-mile and 4-mile distances, taking place May 8 in Key West, Florida. The race starts at 6:00 AM from 3841 N Roosevelt Boulevard. Entry is $75.00. Competitors can choose between the longer 12-mile course or the shorter 4-mile option, making this event accessible to paddlers at different fitness levels. The early morning start time is typical for water-based events in warm climates, allowing athletes to complete their race before peak heat. Key West's location at the southernmost point of the Florida Keys offers unique paddling conditions worth considering when planning your travel and race logistics.
From the Race 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. 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.
Hotels Near This Race
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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
When is Key West Paddle Classic 2027 2027 — Key West, FL?
Key West Paddle Classic 2027 2027 — Key West, FL takes place on May 8, 2027. The race is held in Key West, Florida.
Where is Key West Paddle Classic 2027 2027 — Key West, FL held?
Key West Paddle Classic 2027 2027 — Key West, FL is held at 3841 N Roosevelt Blvd in Key West, Florida.
Where can I find hotels near Key West Paddle Classic 2027 2027 — Key West, FL?
RaceHotelFinder shows hotels sorted by distance from the race venue in Key West. Use the map or list view on this page to compare options and book race weekend accommodation.
