Young eatery owners today aren’t becoming their parents.

No matter how large a legacy they carry, it makes more sense to begin modestly these days, in many cases with a food truck.

BEYOND CAPT’N CON’S

The day Hurricane Milton’s storm surge destroyed the restaurant that her mother had run all her life, Rachel Wilson said sadly, “It’s been a good run. I was blessed with 35 years of growing and learning in this building.”

Then she unwittingly predicted the future by adding, “Those walls contributed to so much of who I am today” — a hardworking heir to her mother’s legacy.

Built in 1904 in Bokeelia, at the northern tip of Pine Island, just south of Punta Gorda, the rambling building that would house Capt’n Con’s Fish House had many lives — most real, some apocryphal.

In the days when Bokeelia’s remote location meant taking judicial matters into local hands, a tree (still there) was said to be used for hangings. Once home to the island post office, a boarding house, a general store and several restaurants, any structure with that much history, folks figured, must be as famous for its ghosts as for the legendary pies it had sold for 45 years.

Wilson busted the spectral part of the story.

“Back in high school, Mom would let us stay the night for slumber parties,” she said. “We never saw anything.”

It’s fair to say that her mom, Luretta Williams-Sims, was the real spirit of the place.

Williams-Sims first started working there in 1979, when it was the Sea Breeze, and returned in the early 1980s after it had become the Crab Shack, owned by Gary and Regina Krivacs.

When the namesake owner of Capt’n Con’s, Hugh Connelly Clayton, died, his heirs, disheartened by the offseason, nearly gave it all up.

Williams-Sims wasn’t having it; she bought the name and the business on Dec. 1, 1995.

“We were planning our big 30-year celebration for 2025,” Wilson said. “Everything was devastating about losing it to Hurricane Milton. My mom’s whole identity, her whole adult life, was that restaurant.

“But I told her, ‘No, Mom, we can still make your pies.’”

Wilson got a license and a commissary, and kept going under the moniker Jolly Rogers & The Captain’s Pie Shoppe. The first weekend, she sold almost 70 pies and kept on baking with the help of Matlacha’s Sweet Floret Cakery and Bokeelia’s Salty Girl Island Café.

Six months later, Wilson achieved her goal of a food trailer, which she’s been using ever since, baking the same pies she’d learned to make while in middle school. Originally, her mother made 14 kinds. Now, it’s more than 30.

“I just love to bake,” Wilson said.

The Capt’n’s bestsellers were always cream pies, from peanut butter to coconut and banana cream, and of course key lime.

“They’re why I immediately filed my paperwork, got my business license, got my commissary,” Wilson explained. “Otherwise, cottage law would’ve let me make only fruit pies, which don’t need refrigeration.”

And the Jolly Rogers part?

Knowing even before they lost it that their family’s time with Capt’n Con’s would be short, Rachel and her husband, Roger, a commercial fisherman, had always planned to launch an eponymous food truck named Jolly Rogers. After Milton destroyed the restaurant, it became a rolling storefront for both seafood and Capt’n Con’s pies.

“The Florida commercial fishing industry is slowly dying, and it’s really sad to see,” Rachel said. “That’s why I emphasize the fresh crab, fresh fish, fresh shrimp, everything local here to Southwest Florida. I do primarily crab dishes — crab cakes that are 95% blue crab, soft-shell crab and crab salad sandwiches — because that’s what he mostly goes after. In the winter months, I might do fresh mullet, snapper or grouper.

“In the summer, I try to take the truck out every Saturday, and in season, I try to go out every Friday night and Saturday. During the week I focus on preorder and delivery for the pies and the same seafood chowder that my mom made, with shrimp, fish, scallops and clams.”

Williams-Sims’ most popular items, the pies and chowder, now live on beyond Capt’n Con’s.

Jolly Rogers & The Captain’s Pie Shoppe ($$), 239-878-6317, provides pie and chowder ordering information and posts the truck’s location on Facebook. Delivers to Punta Gorda, Cape Coral, North Fort Myers, Matlacha and Pine Island. Look for the Jolly Rogers truck from 5 to 8 p.m. at Downtown Kava, 1009 Taylor St., Punta Gorda, on Saturday, Aug. 1, and for The Captain’s Pie Shoppe pies at Salty Girls Island Café, 10700 Stringfellow Road, Suite 30, Bokeelia.

FROM SERVICE TO SERVICE

Fernando Pupo‘s Sergeant’s Cuban Express is one of those food trucks that nails success by specializing in one food, then delivering the best version of it in town.

Born in Miami, Pupo used his college degree to do government contract work in ops and logistics after 12 years in the U.S. Marines.

When government work started drying up, he decided to build something of his own, inspired by his mother, Margarita, with whom he’d planned to start the truck until her recent death.

Sergeant’s serves not only potent Cuban coffees but also a viral Cuban sandwich stuffed with tender, slow-roasted pork plus the usual ham, Swiss, pickles and mustard. There are Cuban pastries, too, but that sandwich is what’s drawing customers.

David Mone of North Port stopped by one day to get his wife, Maria, two of them — one for lunch, another for a snack later.

“As far as my wife’s concerned, this is the best Cuban sandwich around,” David said.

Sergeant’s Cuban Express ($-$$), 941-300-0471, is often open 9:30 or 10 a.m. to 2 p.m., at Lowe’s, 5601 Tuscola Boulevard, North Port. Check its schedule on Facebook.