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Best Kentucky Derby Watch Parties in Southwest Florida

It’s off to the races with these Derby-themed events that bring big hats, bourbon cocktails and Southern charm to local restaurants, bars and social clubs.

BY April 27, 2023
Derby Watch Party
(Photo by Paula Bowes/Courtesy Naples Therapeutic Riding Center)

Don your most extravagant topper and enjoy the flowing mint juleps and bourbon while cheering on your favorite steed among friends and neighbors in Southwest Florida. 

Local establishments celebrate the 149th edition of the Kentucky Derby on Saturday, May 6, in jubilant fashion, with live streams of the race, festive fashion contests, drink specials, fundraisers for local nonprofits and live entertainment—all with signature Southern charm. Celebrating at home? Try this iconic Derby-day drink for your viewing party.


Kentucky Derby Party at Naples Therapeutic Riding Center, Naples

Hit the stables to watch the spectacle unfold. Naples Therapeutic Riding Center hosts Bubbles Mobile Bar, a remodeled 1965 vintage Italian truck, serving up Champagne upon arrival, as well as hors d’oeuvres and dinner catered by SWFL Catering & Events. Proceeds benefit the organization’s equine therapy services.

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Run for the Rosés: Kentucky Derby at The Hampton Social, Naples
Style meets substance at this Mercato restaurant, where the coastal-glam decor and live music provide the perfect backdrop to party all day. Win prizes for best hat and best dressed. Enhance the experience with a VIP ticket that includes admittance into the exclusive Rosé All Day Lounge for up to eight guests, sparkling rosé, shareable snacks and, of course, mint juleps.

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Kentucky Derby Party at The Sports Room, Bonita Springs 

Any betting man (or woman) should jet over to The Sports Room at the Bonita Springs Poker Room for the day. Watch the action from the state-of-the-art room that has stations with personal TVs (must be reserved in advance) and large LED screens.

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Hats & Horses Celebration at The Ritz-Carlton Golf Resort, Naples [SOLD OUT]

Cheer on your favorite horse and rider from the elegant backdrop of The Ritz-Carlton Naples, Tiburón’s Bella Vista Lounge, overlooking the 18th hole of the Tiburón Golf Club. The Forbes Four Star, AAA Four Diamond property serves up food and drink specials, like bourbon flights and mint juleps. There’s also live music between races, and the restaurant doles out prizes during the best hat contest.

Call 239-593-2000 to inquire. Get Tickets


Derby Party at Joey’s Pizza and Pasta, Marco Island

The Optimist Club of Marco Island holds its annual Derby fundraiser at Joey’s Pizza and Pasta House, with a buffet dinner of pastas, salads and appetizers. In between dining, guests participate in a 50/50 raffle and silent auction, with proceeds going toward sport equipment, field rentals and other sports-related fees. VIP and general admission tickets available.

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Annual Kentucky Derby Event at Stillwater Grille, Fort Myers

Stillwater Grille and its hospitable owners bring a cheerful vibe to its annual Kentucky Derby event. Sip from more than 20 bourbons at the bar, donate to the charity fundraiser, and Don festive garb for the best-dressed and best-hat contests.

Call 239.791.8554 to inquire.


Run for the Roses Celebration with Edison Pageant of Light, Fort Myers
They say the sequel is never better than the original, but Edison Pageant of Light begs to differ. The second-annual Run for the Roses Party fundraiser takes place at The Landings Yacht, Golf, and Tennis Club, with proceeds benefiting the nonprofit that celebrates the legacy of seasonal Fort Myers resident, inventor Thomas Edison. Wear your finest fascinator and sports coats, and bring your betting spirit for a friendly wagering on Kentucky Derby squares. Tickets required in advance.

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Kentucky Derby Party with Women’s Council of REALTORS® Cape Coral-Fort Myers, Cape Coral

Network with local female realtors at Stevie Tomato’s Sports Page. Enter to win prizes for best-dressed and dine on traditional pub-style food and drinks.

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Run for the Roses with Charlotte Harbor Sunset Rotary, Punta Gorda
Make your Kentucky Derby viewing a magical one with the Charlotte Harbor Sunset Rotary. The club brings mentalist  Laurence Francis to the party for a spellbinding night, complete with a Derby bingo contest, best-hat contest and prizes.

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America’s Day at the Races with Scotty’s Bierwerks, Cape Coral

The popular brewery, known for its small-batch concoctions, transforms into a race-day scene with TV projectors inside the taproom and food trucks outside. Try your luck at any of the wagering contests and raffles for gift baskets and gift cards to other local restaurants, food trucks and bars throughout the day.

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