Key West Party Fun at the Poker Run

There is no better place for a weekend motorcycle ride than the beautiful coastal highway of Florida’s Key West. When you add in some wild party fun, contests with fabulous prizes, and a commitment to community charities, you have the recipe for the perfect island paradise weekend!

Phil Peterson’s 40th Key West Poker Run festivities kick off on Thursday, September 13th with the 5th Annual Bike Week Bar Stroll & Upper Duval Crawl, beginning at 5:00 p.m. at Southernmost Beach Café. An event t-shirt and map to participating bars (each offering a free drink) can be purchased for $25. Cowboy Bill’s Saloon will host the Fast Wheels & High Heels event on Friday night at 9:30 p.m., featuring several contests for cash and prizes, including the Biker Babe Sexy Bull Riding Contest.

The Poker Run ride takes place on Friday and Saturday from Miami to Key West, beginning at 8:00 a.m. at Peterson’s Harley-Davidson South, 19825 South Dixie Highway, Miami or at Peterson’s Harley-Davidson of Miami, 19400 NW 2nd Avenue, Miami. Purchase event t-shirts, raffle tickets and other memorabilia at Peterson’s and at stops throughout the ride, including at the Conch Republic Seafood Company at 631 Greene Street, Key West. Participants who draw cards at all five stops are eligible to enter the Furthest Traveled Contest. Duval and Greene Street are closed to traffic for this event, with the Vendor Village on Greene Street offering plenty of motorcycle accessories and apparel for sale throughout the event.

Friday night fun starts at 5:00 p.m. at Schooner Wharf Bar’s Welcome Party and Hog Roast, featuring Schooner’s famous pork barbeque and live music. Saturday’s events include the Rick’s/Durty Harry’s Bike Show at Duval and Greene Streets, with awards offered in 24 classes. A $25 registration fee benefits the Diabetes Research Institute and the Key West Sunrise Rotary Club. The Southernmost Hotel Collection will host the Biker Bash Pool Party at the Pineapple Bar from noon to 4:00 p.m. at 1319 Duval Street, and Sloppy Joe’s Bar will host the Biker Bash Beer Garden from noon until 11:00 p.m. with live music, contests and games. The 18th Annual Blessing of the Bikes will be held at Indigenous Park on White Street at 1:00 p.m. Head back to Schooner Wharf Bar Saturday night for their Paradise Tattoo Show and Contest and the Biker Babes  burlesque show.

The Poker Run contest’s Texas Hold’Em Grand Finale will be held at 11:00 p.m. Saturday night at Cowboy Bill’s Saloon. Participants with the ten best poker hands will compete to win a brand new Harley-Davidson Sportster 883 Iron or $6,000 in cash! Winners of other contests and the event raffle will also be announced at Cowboy Bill’s. The fun wraps up Sunday, September 16th with the Biker Bloody Mary Brunch at The Southernmost Beach Café at 1405 Duval Street from 10:00 a.m. to 2:00 p.m.

Every day is a party in our island paradise of Key West! What makes the party even more special is that the people of Key West always give back to the community by supporting local charities. I have been selling Key West real estate in our island community for over 29 years; let my experience, personalized service, and free relocation packet help you find the perfect island paradise home. Contact me today by phone at Margarita Villoch, 305-304-8505, by email at, or on the web at and join the Key West party!