Dapper D’s Cigars Downtown tops $530,000 investment

[JohnS]

Dapper D’s Cigars Downtown tops $530,000 investment

The restaurant, lounge and bar is building-out along Ocean Street between Bay and Forsyth.

By Karen Brune Mathis - December 4, 2025

A rendering of the sign planned for Dapper D’s cigar bar and restaurant at 11 Ocean St. 

Dapper D’s Cigars Restaurant Lounge and Bar is ramping up to build-out Downtown.

The city issued a permit Dec. 3 for the $516,571 project at 11 N. Ocean St., following permits for signage Aug. 22 at $6,500 and plumbing Oct. 30 for $8,500.

That boosts the total work to $531,571.

DePratter Construction Group Inc. is the contractor, along with Signarama Jacksonville for the sign and Famous Plumbing. All are based in Jacksonville.

The Downtown Investment Authority board voted July 16 to provide public funding for Dapper D’s in Jacksonville’s historic core.

Darian “Jack” Jackson launched his first Dapper D’s Cigars in 2020 in River City Marketplace in North Jacksonville. Photo by Jeffrey Leeser

With a 7-0 vote, the DIA board approved a $187,620 grant for the proposed establishment at the two-story, 3,674-square-foot building that previously housed the Island Girl Cigar Bar between Bay and Forsyth streets.

Darian “Jack” Jackson, owner of Dapper D’s Cigars Downtown LLC, and Austin Towery, managing member of 11 Ocean LLC, the landlord, co-applied for the grant under the DIA’s Food and Beverage Retail Enhancement Program.

Towery also applied for a $29,952 DIA Facade Grant to improve the appearance of the exterior of the building. 

The larger DIA grant will be structured as a forgivable, no-interest loan scheduled to amortize at 20% annually for five years providing that business operations continue uninterrupted. 

The DIA board approved both grants.

A rendering of the second-floor cigar lounge and bar planned for Dapper D's Cigars, restaurant, lounge and bar Downtown at 11 N. Ocean St.

Dapper D’s Cigars Downtown is planned as a fast-casual restaurant downstairs with a menu focused on Philly cheesesteak sandwiches and a casual bar that will serve beer, wine and mixed drinks. 

The second floor, which has its own entrance at the sidewalk and with what is described as an extensive ventilation system, will house the cigar lounge, humidor and an upscale cocktail bar. 

Jackson owns and operates two Dapper D’s cigar lounges, in River City Marketplace in North Jacksonville and in The Fountains at St. Johns in Northern St. Johns County. 

Dapper D’s Cigars Restaurant Lounge and Bar will be in the former Island Girl Cigar Bar and next to Cowford Chophouse (on right) at 101 E. Bay St. Photo by Monty Zickuhr

A DIA staff report on the incentive request says the Downtown location, like the others, will have a large humidor with more than 700 cigars that can be enjoyed on premise, taken home or delivered anywhere in the U.S. and Canada. Unlike the other locations, Dapper D’s Downtown will have an extensive bar and whiskey collection.

Jackson was named one of the Jacksonville Daily Record Top Entrepreneurs 2025 and was in a recent class of Leadership Jacksonville and the Hightower Fellowship. 

Source: https://www.jaxdailyrecord.com/news/2025/dec/04/dapper-ds-cigars-downtown-tops-530000-investment/

[Chas.Alpha]

I’m happy to see that. Island Girl was my stop if I wanted a smoke on my way home from work when I lived in J’ville. I hope they continue the free valet, as parking is a challenge on the weekends.