The Downtown Investment Authority Retail Enhancement and Property Disposition Committee will consider a grant request for a new restaurant and cigar bar when it meets at 10 a.m. July 10 in the Multipurpose Room at the Main Library Downtown.
Darien “Jack” Jackson, owner of Dapper D’s Cigars Downtown LLC, and Austin Towery, managing member of 11 Ocean LLC, the landlord, are co-applicants for a $187,620 grant request.
The application indicates a total build-out cost of $516,571 for the renovation of the building at 11 Ocean St.
According to the staff report, the request is for funding under the Food and Beverage Retail Enhancement Program Grant to update and build-out a restaurant and cigar and cocktail lounge. The space, on Ocean Street between Bay and Forsyth streets, previously housed the Island Girl Cigar Bar.
Towery also is applying for a $29,952 DIA Facade Grant to improve the appearance of the exterior of the building.
If approved, the larger grant will be structured as a forgivable, no-interest loan that will amortize at the rate of 20% on each anniversary date of the closing for five years so long as business operations as proposed in the business plan continue uninterrupted unless otherwise modified with DIA approval, subject to force majeure, and no uncured event of default exists.
Each co-applicant will be a personal guarantee party to the forgivable note and loan agreement.
Jackson owns and operates two Dapper D’s cigar lounges in River City Marketplace and in northern St. Johns county.
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.
The staff report 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 which is the natural accompaniment to a cigar lounge, it states.
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.