Like Running or Walking? Love Wine? This race is for you! Join us on Sunday, December 19, 2026 at 9:00am and 11:00am (you will select your start time during registration) for an exciting Christmas themed event that features the scenic views of Aspirations Winery! Located in sunny Clearwater Florida, we hand-craft over 30 wines every year, right here at our veteran and family owned & operated craft winery. Although we specialize in making some of the tastiest award winning, fruit-infused wines around, we also produce your favorite dry reds, whites as well as some dessert wines. So, whether you are looking to run, walk or just enjoy the wine this race is a sure thing for a great time and an incredible experience! This race is timed and scored by J3 Timing . Results will be posted at www.J3Timing.com . Registration Includes: T-shirt : Super Soft Ring Spun Cotton short sleeve red t-shirt included or you can upgrade to a long sleeve black shirt for $5 Wine Glass : Shatterproof, Collapsible,
Hotels Near This Race
Find accommodation close to the start line in Clearwater, FL. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
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Aspirations Christmas Wine Run 5k 2026 — Clearwater, FL
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Race Travel Insurance
Don't forget travel insurance for December 19.
You've trained for months and booked a trip to Clearwater, 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
