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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 29, 2022
(Photo by Lauren Marie)

There’s more to the Kentucky Derby than the blink-and-you-miss-it horse races. With a tradition around fanciful hats, an official drink and tons of Southern style, the annual Run for the Roses has a whole culture around it that makes for a stellar party. On the Gulf, we embrace the celebrations wholeheartedly with drink specials, live entertainment and fashion contests in Naples, Bonita Springs, Fort Myers, Marco Island and Cape Coral. In true Southwest Florida spirit, many of these Derby events benefit local nonprofits. 

So, if you can’t make it to Churchill Downs this year, break out your seersucker, don your best fascinator and race to these parties, where you can raise a mint julep cup to the 148th annual running of the Kentucky Derby. All events take place on Saturday, May 7th, and include a live stream of the races, unless otherwise noted. Try this iconic Derby-day drink if you opt for an at-home viewing.


Kentucky Derby Party at Naples Therapeutic Riding Center, Naples

What better place to catch the Kentucky Derby than at the stables? The Naples Therapeutic Riding Center nonprofit invites horse lovers to the center for bites from Delicious by Design and sponsorship packages that include wristbands for the open bar. Proceeds benefit the program’s equine therapy services for children and adults with special needs and mental health disorders. >> Get Tickets  


Hats & Horses Celebration at The Ritz-Carlton Golf Resort, Naples

Watch the races at the elegant resort hotel, where the festivities take place at the Bella Vista Lounge, overlooking the 18th hole of the Tiburón Golf Club. For the occasion, the lounge serves unique takes on the mint julep and light snacks. Call 239-593-2000 to inquire. >> See More 


Run for the Rosés: Kentucky Derby at The Hampton Social, Naples 

The Mercato restaurant provides the perfect backdrop for your Derby fashion, with its summery interiors and rosé-all-day vibe. You can book a VIP Experience for up to eight friends, with bottles of sparkling pink wine, mint juleps and snacks for the group. In addition to the live stream of the races, there will be live music and a photo booth to document your style. Don’t hold back—Hampton Social is awarding prizes for best dressed and best hat. >> Book a Table or VIP Experience


Derby Dash, Naples Junior Woman’s Club, Naples 

One of the biggest annual socials for the Naples Woman’s Club, the Derby Dash features a silent auction, betting games, music, and food and drinks to enjoy while watching the races. Ladies and gentlemen are welcome, and proceeds go toward the club’s scholarships awarded to local high school seniors. >> Get Tickets 


Derby Watch Party at Southern Kitchen & Raw Bar, Naples  

Leave it to a Southern restaurant to do it up for this Kentucky tradition. The waterfront restaurant, which has a patio overlooking Naples Bay, will be doling out prizes for most original hat, Champagne specials and themed appetizers for its Derby Watch Party. >> Call 239-331-4821 to Book a Table 


Derby de Mayo at Marco Island Brewery, Marco Island 

The Optimist Club of Marco Island, which benefits local youth sports, combines two of May’s liveliest holidays for this fundraiser. A Mexican buffet honors the Cinco de Mayo festivities, while the hat and best-dressed contests celebrate the Derby’s fashionable traditions. >> Get Tickets 


Derby Party at Seaside Bar, Bonita Springs 

The two-year-old Seaside Bar in Bonita throws a seriously good party, thanks to its indoor-outdoor bar area and loft setup with an upstairs DJ booth and lounge. The restaurant brings back its Kentucky Derby party this year, with live country music, mint juleps and specials on their high-end bar food all day. >> Call 239-288-1470 for reservations 


Kentucky Derby Party at the Brass Tap, Bonita Springs 

Those wanting to bet on the races can head to the Brass Tap at the Bonita Springs Poker Room. Zimco Entertainment produces the event, with more than a dozen TVs streaming the races and the option to participate in charity wagers. Do it up with your seersucker, sundresses and statement fascinators—the restaurant will hand out awards for the best-dressed individual and couple and most over-the-top hat. >> Book your spot


Kentucky Derby at Vichino’s Cafe & Wine Bar, Bonita Springs 

The recently opened Vichino’s is already making a name for itself with its coffee and from-scratch pastries, served fresh all day, and wine bar vibe at night. The stylish locale hosts bingo, live music and a hat contest for its Kentucky Derby festivities. >> Call 239-317-2146 for Tickets ​​


Run for the Roses at the Crowne Plaza Fort Myers at Bell Tower Shops, Fort Myers 

The female empowerment Zonta Club of Fort Myers hosts this Derby celebration with a bourbon tasting, games, raffles, and Southern drinks and snacks. Wear your flashiest, fun hats and bowties for the best-dressed contests. Proceeds benefit charity. >> Get Tickets 


Derby Day at Oxbow Bar & Grill, Fort Myers 

Catch the “greatest two minutes in sports” at the Luminary Hotel & Co.’s Oxbow Bar & Grill, where the Caloosahatchee River and bridge views rival the action on TV. Mint juleps made with Four Roses Bourbon are $9 all day, and anyone wearing a hat gets a shrimp cocktail when they arrive. The party starts at 2:30 p.m. >> Reserve a Table 


Kentucky Derby & Fundraiser at Overtime Pizzeria & Sports Pub, Cape Coral 

Funky outfits are encouraged for this race-day party with a buffet and best-dressed contest at Overtime Pizzeria. Proceeds benefit the Women’s Council of REALTORS® Cape Coral-Fort Myers, which aims to help women advance in the industry. >> Get Tickets 


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