The Downtown Investment Authority board voted unanimously July 16 to provide public funding for a new cigar bar and restaurant in Jacksonville’s historic core.
With a 7-0 vote, the board approved a $187,620 grant for the proposed establishment at 11 Ocean St. The space, between Bay and Forsyth streets, previously housed the Island Girl Cigar Bar.
Darien “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 DIA approved both grants as consent agenda items, with both having previously been approved in committee.
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, one in River City Marketplace in Jacksonville and another in The Fountains at St. Johns in Northern St. Johns County.
A 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.
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.