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Content Dapper D's co-owner Darian "Jack" Jackson at the rail of the upstair cigar bar.

Dapper D's Cigars & Restaurant to open downtown May 15

May 07, 2026

Jacksonville’s Elbow District will continue its dining and entertainment growth when Dapper D’s Cigars & Restaurant opens its downtown location on May 15.

According to its co-owner Darian “Jack” Jackson, there will be plenty of people lining up for the celebration of live music, food, cocktails and high-end cigars.

“We’ve already had roughly 100 people walk in here from the street,” Jackson told the Business Journal. “That's how good everything looks over here. We're super excited about it. And I think it's going to be a good turnout for downtown Jacksonville.”

The Friday opening will culminate more than a year of planning and preparation to renovate the former Island Girl Cigar Bar into a two-floor fast-casual restaurant downstairs and a luxury cigar bar upstairs at 11 Ocean St.

The location will add to a growing commercial corridor that’s seen significant evolution in the past two years with the addition of Circuit Arcade Bar, which sits next door to Dapper D's, the three-story Decca Live music venue with a rooftop bar and Keane's Irish Pub.

Dapper D’s founders Darian "Jack" Jackson and Ranisha Jackson plan to elevate this culinary and celebratory mix and contribute their effort to uplifting Jacksonville’s urban core.

Dapper D’s will bring a slice of Philly to downtown with its cheesesteaks, Jackson said.

“The recipe comes from a long lineage of cheesesteak makers in Philadelphia. We have what the authentic Philly cheesesteak looks like by Philadelphia standards, and we're super excited to be bringing that authentic experience to Jacksonville,” Jackson said.

Bread will come directly from Philadelphia breadmaker Luciano Calandra of Calandra's Bakery. The restaurant will also fire up cheese from authentic Cooper’s cheddar out of Philly.

“We're super excited about that. We will be the only company in Jacksonville that has this bread,” Jackson said. “And if you know a good Philly in Philadelphia, they’ve got Cooper sharp on there.”

There will be counter service that includes beer and wine along with approximately 30 table seats and bar seating under murals from local artist Tierra Scott.

Upstairs, large leather seats sit under dark blue Art Deco patterned wallpaper, and blue felt seats belly up to a full bar and celebrated selection of cigars that Jackson has established since opening the first Dapper D’s in River City in the city's Northside.

“It’s a premium cigar experience,” Jackson said.

Jacksonville-based DePratter Construction Group oversaw the estimated $516,571 renovation, which spans 2,100 square feet on the ground level and 1,800 square feet on the upper level.

Dapper D’s cheesesteak restaurant will be open from 11 a.m. to 10 p.m. Sunday through Wednesday and until 11 p.m. Thursday through Saturday. The cigar bar will be open from 10 a.m. to 11 p.m. Sunday through Wednesday and from 10 a.m. to midnight Thursday through Saturday.

By Matt Denis
Jacksonville Business Journal

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