Darian “Jack” Jackson, owner of Dapper D’s Cigars, is opening a restaurant and cigar lounge at 11 N. Ocean St. Downtown.

It will be his third location in Northeast Florida.

It is in the former Island Girl Cigar Bar and next to Cowford Chophouse at 101 E. Bay St.

Jackson bought the property April 30 for $146,225.

He plans to use the two-story building for a restaurant on the ground floor offering Philly cheesesteak sandwiches and wings, and a self-contained space upstairs for a cigar lounge.

Jackson’s other Dapper D’s Cigars are at 725 Skymarks Drive in River City Marketplace in North Jacksonville and 150 Fountains Way in The Fountains at St. Johns in Saint Johns.

The new location will be called Dapper D’s Cigars and Cheesesteaks.

“There are a lot of Philadelphia natives who live in Jacksonville and we want to bring the true Philadelphia cheesesteak experience,” Jackson said.

The downstairs is 2,100 square feet and the upstairs is 1,800 square feet.

Jackson has a full liquor license to serve the restaurant and cigar lounge.

He hopes to open by the end of summer or early fall.

He estimates construction costs at $400,000. DePratter Construction Group of Jacksonville is the contractor.

“We’re coming with the top cheeses that you would normally get from Philly.”

Jackson is remodeling the interior to brighten the dark space, build a kitchen and enclose the upstairs. He said because the upstairs is enclosed, he said he can allow smoking inside.

“We have one on the Northside coming into the city of Jacksonville and we have one on the Southside coming into the city of Jacksonville. So Downtown was the ideal location for us to go next,” he said.

“It puts us at a 20-minute advantage either way you go. Whether you’re heading out of the city or into the city, you have a Dapper D’s spot in the middle now.”

Jackson, one of the Daily Record’s 2025 Top Entrepreneurs, sees this as an opportunity to get involved in Jacksonville’s urban core.

“We would love to be a part of the new wave of Downtown that Jacksonville was about to experience,” he said.

“This Downtown area can be very similar to Chicago or Savannah, or any other major city, so we want to be a part of that.”

He expects to employ two full-time employees and 12 part-time to start.

The restaurant and cigar lounge will be open from 11 a.m. to 11 p.m. daily.