Kentucky Derby Watch Party

Join us for an unforgettable afternoon of high style, spirited sips, and heart-pounding horse racing in the heart of downtown Naples during the Kentucky Derby on Saturday, May 3, 2025.

Join us at the Inn on Fifth’s pool terrace from 5:00 – 7:00pm to watch the iconic races, enjoy Derby-inspired bites and beverages, live music performances by the talented artists from United Arts Collier, and more. “Best Hat” & “Best Dressed” contests, “Derby Day” giveaways and other festive fun will add to the afternoon, hosted in collaboration with the Naples Brunch Club and Vespa Naples.

Shop an Exclusive Collection of retail items from local vendors, including our partners at Provident Jewelry who will be featuring a curated selection of Gucci’s new equestrian-themed designs and men’s watches, all available for purchase. Provident Jewelry is extending a 10% discount —excluding Cartier and Rolex—valid only on May 3 for watch party attendees.

Vespa isn’t just a scooter — it’s a lifestyle of freedom, flair, and timeless Italian style. Make every ride an experience that turns heads and inspires adventure.

As a special treat, all Inn On Fifth Derby Watch Party guests receive $200 off the purchase of any Vespa scooter — just show your event wristband at the Naples dealership.

Adding to the celebration, United Arts Collier will be showcasing an inspiring collection of original artwork from local artists, also available for purchase.

VIP Experience – Hospitality Suite  + Pool Terrace Access | $125 per person

• Step into cool, air-conditioned luxury in our exclusive indoor Hospitality Suite, lounge seating, with large screens, in-and out access to the pool terrace for outdoor viewing
• Bottomless Lallier Champagne, the official champagne of the 2025 Oscars (all other drinks & cocktails available for purchase)
• Derby-inspired hors d’oeuvres
• Automatic entry in the VIP Raffle for a chance to win a one-night future stay in a Club Level Suite and a spa treatment for two at the Inn

From fascinators to fedoras, bowties to bold prints—style takes center stage as we toast to tradition and celebrate the Run for the Roses in true Fifth Avenue fashion. Ladies, this is your chance to turn heads in your most fabulous Derby dress and show-stopping hat. Gents, come dressed to impress in your sharpest suit or sport coat.

Tickets are limited and available on a first-come, first-served basis. Reserve yours today.