Pensacola Cigar Weekend
A premium, multi-day celebration of culture, community, and the finest cigars, in the heart of Pensacola, Florida.
Save the Date
Pensacola Cigar Weekend 2027
Embers & Elegance
May 14th - 16th
Mark Your Calendars.
Tell Your Crew.
Start Planning Your Trip.
What is Pensacola Cigar Weekend?
Pensacola Cigar Weekend is a premium, multi-day event in Pensacola, Florida, bringing together cigar enthusiasts and luxury lifestyle connoisseurs. Founded by the Herf Collective, it's a celebration of culture, community, and connection blending education, entertainment, and hospitality for newcomers and aficionados alike.
2026 Derby Edition — Photo Gallery
The 2026 Derby Edition brought together style, smoke, and community in unforgettable fashion. Browse the full gallery and relive the moments that made it one of the best events on the emerald coast.
Event
Pensacola Cigar Weekend: Derby Edition
Year
2026
2027
Main Event Venue
museum plaza
Downtown Pensacola
Located in the heart of Pensacola, this venue puts you steps away from the city's best restaurants, bars, and nightlife. Ample parking is available nearby, and the area is easily walkable from most downtown hotels.
Museum Plaza,
Downtown Pensacola, FL
Sunday Farewell Mixer (VIP Only)
VENUE: CORDOVA CIGARS
DRESS: CASUAL
Close out Pensacola Cigar Weekend at the VIP Farewell Mixer, an exclusive Sunday gathering where guests enjoy one final cigar, wine, brunch charcuterie and relaxed conversation as the Derby Edition weekend comes to a memorable close.
Saturday The Main Event: Run for the Roses
VENUE: MUSEUM PLAZA
DRESS: FINEST KENTUCKY DERBY THEMED ATTIRE
The Main Event: Run for the Roses General Admission Ticket: Celebrate tradition, taste, and timeless style with the Run for the Roses General Admission ticket. Enjoy access to Saturday's main event, filled with fine cigars, Starz Band Live, live DJ, and Derby-inspired elegance. Dress to Impress in your finest dresses, suits, fascinators, and fedoras, sip your mint julep (or favorite cocktail), and experience the charm of Southern luxury at its finest.
Saturday: VIP Only Pre-Event Mixer
VENUE: MUSEUM PLAZA
DRESS: FINEST KENTUCKY DERBY THEMED ATTIRE
Step into the experience early at the VIP Only Pre-Event Mixer, where VIP guests gather for premium cigars, curated spirits, and elevated conversation before the excitement of the Run for the Roses main event begins.
Friday: Kickoff Mixer
VENUE: BLEND LOUNGE
DRESS: CASUAL
Kick off Pensacola Cigar Weekend at the Friday Mixer at Blend Lounge, where guests gather for great drinks, lively conversation, and the first sparks of cigar camaraderie that set the tone for an unforgettable Derby Edition weekend.
Friday: VIP Only Mixer
VENUE: CIGAR FACTORY SOCIAL CLUB
DRESS: CASUAL
Begin Pensacola Cigar Weekend in elevated style at the exclusive Friday VIP Mixer at Cigar Factory Social Club, where VIP guests gather for premium cigars, curated spirits, and intimate conversation to set the tone for an unforgettable Derby Edition weekend.