Talk Derby To Me

Kentucky Derby Event at Corkscrew – Event Brite Outline

Join Corkscrew Wedding & Winery, Rosehouse Catering, and The Scout Guide Naples and Fort Myers for an unforgettable Kentucky Derby Extravaganza . Our event at the breathtaking Corkscrew Wedding & Winery venue is set to welcome an elite and dynamic crowd, all eager to embrace the spirit of Derby Day in true style. Dressed to impress, these patrons know the stakes are high for our Best Dressed Contest, where fashion and flair take center stage. Expect a sea of day dresses, statement hats, seersucker suits, and polished Derby ensembles as guests bring their A-game for an afternoon of sophistication, celebration, and spirited competition.

Among our distinguished attendees are young professionals, entrepreneurs, influencers, business owners, and tastemakers from across Captiva, Sanibel, Cape Coral, Fort Myers, Estero, Bonita Springs, Naples, Estero and Marco Island. Many are Scout Guide members, eager to expand their networks and engage with like-minded peers, while others are prospective members curious to explore the discerning community that The Scout Guide represents. This event is also a shopper’s paradise, attracting those who love discovering unique gifts, boutique finds, and unique goods from our carefully curated vendor bazaar.

Beyond the networking and shopping, this gathering is a must-attend for event planners and producers, who are excited to experience firsthand the beauty and versatility of Corkscrew Wedding and Winery as a premier venue. And of course, no Derby celebration is complete without an indulgence in exquisite food and drink. Guests will revel in a race-day-inspired culinary journey, sipping on fine wines, craft brews, and handcrafted cocktails, expertly paired with exceptional catering by The Rose House Naples and other top-tier vendors.

Ultimately, our guests are coming to celebrate, connect, and indulge—to toast to another incredible season in Southwest Florida and to simply have an unforgettable time with friends on a beautiful Saturday in May. With the thrill of the races, the charm of Southern hospitality, and an atmosphere brimming with elegance and excitement, this event promises to be a standout moment of the season.

Ticket Pricing & Access

1. Early Bird General Admission – $75
2. • Available until March 25th.
   • Includes:
   • • Access to:
     • • Property Grounds: Explore the stunning event setting, meet with the Corkscrew team about the potential of the venue and bask in the natural beauty of the grounds.
       • Vendor Bazaar: A curated showcase of 50+ vendors selling goods, hosting for-purchase workshops, and sharing insights on their services. Additional exclusive experiences will be available throughout the property.
       • The Rosehouse Lounge Experience: Enjoy a Derby-inspired atmosphere featuring exceptionally crafted bites and drinks by the Rose House team and their exclusive beverage partner
       • Sips: Two (2) complimentary drink tickets for the Bar Lounge or Welcome Mobile Bar. Additional tickets will be available for purchase at the event.
       • Derby Viewing and Raffles: Access to our indoor and outdoor race day viewing spaces, set up with large screen TV’s, chairs, and lounge seating. Enter our raffles for a chance to win unmatched experiences with our favorite service professionals
       • Premium Experiences: Access to for-purchase premium experiences in the most beautiful spaces of the venue. Think private tastings, private services, one-on-one moments, professional photography and more! Full calendar of events and pricing details to be released soon.
       • Food and Beverage Experiences: : Access to for-purchase food and beverage trucks, in addition to the Rose Lounge Experience
       • Unmatched Networking: with over 300 distinguished attendees are young professionals, entrepreneurs, influencers, business owners, and tastemakers from Fort Myers, Naples, and the entire Paradise Coast.
3. General Admission (Regular) – $95
4. • Pricing effective after March 25th
   • Includes the same access and benefits as the Early Bird ticket.

Please contact us for Sponsorship opportunities, which include select ticket packages and privileges!

Also check out other Sports events in Estero, Workshops in Estero.