Pensacola Cigar Weekend 2026: Derby Edition

Step into the "Winner’s Circle" for a weekend where the heritage of Churchill Downs meets the coastal charm of historic downtown Pensacola. This is not merely an event; it is a curated lifestyle experience designed for the discerning aficionado who appreciates the finer things: premium tobacco, legendary & boutique spirits, high-fashion, and world-class camaraderie.

From our high-energy mixers to the centerpiece Run for the Roses , every moment is crafted to elevate the soul and celebrate the cigar culture. Expect an atmosphere defined by live soulful rhythms, the aroma of the world’s finest leaves, and the vibrant elegance of Derby-inspired style

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Select Your Experience

To ensure your weekend meets your standards of luxury, we offer two distinct tiers of access:

• VIP-Only Mixers for intimate networking.
  Friday: Pre-Meet & Greet Mixer with local business leaders, premium cigar &
  spirit brand representatives, cocktails & tapas.
  Friday, you are also invited to continue the party at the Meet & Greet
  at 200 South Tap Bar following the VIP Pre-Mixer
  Sunday: End the weekend with fellow VIPs, your favorite cigars, a
  curated cigar experience with a chill vibe.
• Saturday Main Event Hospitality: Entry into the main event with
  guaranteed Preferred Seating, an Open Bar, and Small Plate Food
  selections.
• VIP Swag Bag: an exclusive bag filled with a selection of premium cigars
  and with cigar essentials.

• Main Event Access: Full entry to the Saturday "Run for the Roses" featuring
  the Starz Band Live and DJ-J5 .
• Social Mixer: Access to the Friday meet & greet mixer.
• Atmosphere: Enjoy the freedom to smoke,dance, and shop while exploring
  our curated selection of spirit and cigar vendors.

• Friday & Sunday: Casual
• Saturday Main Event: We invite you to "Dress to Impress." Bold suits,
  seersucker, fascinators, and fedoras are highly encouraged to maintain the
  elevated spirit of the gala.

Immerse Yourself in 450 Years of History When you step into Pensacola Cigar Weekend, you are walking through the birthplace of North American history. Our venues are nestled within the red-brick charm of a downtown that has stood under five different flags since 1559. Between the smoke and the music, you’ll experience a city where Spanish, French, and British influences meet modern Southern luxury.

The Intersection of Tradition and Lifestyle Just as a premium cigar takes time to age and perfect, our host city has spent centuries refining its unique character. Choosing to attend the Derby Edition means enjoying your favorite leaf against a backdrop of historic iron-lace balconies and cobblestone streets that have hosted icons for generations.

More Than a Weekend—A Coastal Retreat Beyond the event gates, your ticket is your passport to the "Emerald Coast." Use your downtime to explore:

• The Palafox District: Recently named one of the "Great Streets in America," offering world-class dining and high-end boutiques just steps from our event venues. (Currently undergoing a beautiful revitalization)
• Historic Forts & Maritime Lore: Visit the structures that guarded the Gulf for centuries.
• The World’s Whitest Beaches: Only a short drive or ferry ride away, the legendary white sands of Pensacola Beach provide the perfect Sunday morning reflection before our Finish Line Farewell.

The Ultimate Networking Backdrop There is no better place to forge lasting connections than in a city built on trade, exploration, and hospitality. We invite you to be a part of Pensacola’s living history while creating your own unforgettable moments at the 2026 Derby Edition.

Info: Pre-Meet & Greet Mixer with local business leaders, civic & political leaders, premium cigar & spirit brand representatives, cocktails & tapas.

Info: Kick off the weekend in style at the official opening night celebration! Mingle with fellow enthusiasts and set the pace for a weekend of class and camaraderie. Consider this your first lap toward an extraordinary experience.
Vibe: Social & High-Energy
Refreshments: Cash Bar Available
Dress Code: Casual

Info: Step into the Winner’s Circle for the crown jewel of Pensacola Cigar Weekend! Immerse yourself in an afternoon of a Southern elevated experience, premium spirits, and world-class cigars. Whether you’re dancing to the Starz Band Live, vibing with DJ-J5 or exploring our curated vendor row, this is the ultimate Derby experience.
The Experience: Live music, dancing, and high-end spirit, apparel, and accessory vendors.
The Vibe: Sip a classic Mint Julep, light up a premium cigar, and soak in the elegance.
Access: VIP and General Admission Ticket Holders.
Dress Code: Derby’s Best. Bring out the vibrant dresses, sharp suits, fascinators, and fedoras.

Info: Close out the 2026 Derby Edition with grace and good company. We’re hosting an intimate Sunday gathering for our VIP Ticket Holders to toast to a winning weekend. Enjoy , premium wine and smooth cigars in a relaxed atmosphere, the perfect final stretch for our elite guests.Access: VIP Ticket Holders Only
Dress Code: Casual

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