{"id":357561,"date":"2026-07-30T13:38:07","date_gmt":"2026-07-30T13:38:07","guid":{"rendered":"https:\/\/www.newsbeep.com\/us-fl\/357561\/"},"modified":"2026-07-30T13:38:07","modified_gmt":"2026-07-30T13:38:07","slug":"the-scene-living-legacies-offspring-take-care-of-business-port-charlotte-news","status":"publish","type":"post","link":"https:\/\/www.newsbeep.com\/us-fl\/357561\/","title":{"rendered":"THE SCENE | Living legacies: Offspring take care of business | Port Charlotte News"},"content":{"rendered":"<p>Young eatery owners today aren\u2019t becoming their parents.<\/p>\n<p>No matter how large a legacy they carry, it makes more sense to begin modestly these days, in many cases with a food truck.<\/p>\n<p>BEYOND CAPT\u2019N CON\u2019S<\/p>\n<p>The day Hurricane Milton\u2019s storm surge destroyed the restaurant that her mother had run all her life, Rachel Wilson said sadly, \u201cIt\u2019s been a good run. I was blessed with 35 years of growing and learning in this building.\u201d<\/p>\n<p>Then she unwittingly predicted the future by adding, \u201cThose walls contributed to so much of who I am today\u201d \u2014 a hardworking heir to her mother\u2019s legacy.<\/p>\n<p>Built in 1904 in Bokeelia, at the northern tip of Pine Island, just south of Punta Gorda, the rambling building that would house Capt\u2019n Con\u2019s Fish House had many lives \u2014 most real, some apocryphal.<\/p>\n<p>In the days when Bokeelia\u2019s 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.<\/p>\n<p>Wilson busted the spectral part of the story.<\/p>\n<p>\u201cBack in high school, Mom would let us stay the night for slumber parties,\u201d she said. \u201cWe never saw anything.\u201d<\/p>\n<p>It\u2019s fair to say that her mom, Luretta Williams-Sims, was the real spirit of the place.<\/p>\n<p>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.<\/p>\n<p>When the namesake owner of Capt\u2019n Con\u2019s, Hugh Connelly Clayton, died, his heirs, disheartened by the offseason, nearly gave it all up.<\/p>\n<p>Williams-Sims wasn\u2019t having it; she bought the name and the business on Dec. 1, 1995.<\/p>\n<p>\u201cWe were planning our big 30-year celebration for 2025,\u201d Wilson said. \u201cEverything was devastating about losing it to Hurricane Milton. My mom\u2019s whole identity, her whole adult life, was that restaurant.<\/p>\n<p>\u201cBut I told her, \u2018No, Mom, we can still make your pies.\u2019\u201d<\/p>\n<p>Wilson got a license and a commissary, and kept going under the moniker Jolly Rogers &amp; The Captain\u2019s Pie Shoppe. The first weekend, she sold almost 70 pies and kept on baking with the help of Matlacha\u2019s Sweet Floret Cakery and Bokeelia\u2019s Salty Girl Island Caf\u00e9.<\/p>\n<p>Six months later, Wilson achieved her goal of a food trailer, which she\u2019s been using ever since, baking the same pies she\u2019d learned to make while in middle school. Originally, her mother made 14 kinds. Now, it\u2019s more than 30.<\/p>\n<p>\u201cI just love to bake,\u201d Wilson said.<\/p>\n<p>The Capt\u2019n\u2019s bestsellers were always cream pies, from peanut butter to coconut and banana cream, and of course key lime.<\/p>\n<p>\u201cThey\u2019re why I immediately filed my paperwork, got my business license, got my commissary,\u201d Wilson explained. \u201cOtherwise, cottage law would\u2019ve let me make only fruit pies, which don\u2019t need refrigeration.\u201d<\/p>\n<p>And the Jolly Rogers part?<\/p>\n<p>Knowing even before they lost it that their family\u2019s time with Capt\u2019n Con\u2019s 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\u2019n Con\u2019s pies.<\/p>\n<p>\u201cThe Florida commercial fishing industry is slowly dying, and it\u2019s really sad to see,\u201d Rachel said. \u201cThat\u2019s why I emphasize the fresh crab, fresh fish, fresh shrimp, everything local here to Southwest Florida. I do primarily crab dishes \u2014 crab cakes that are 95% blue crab, soft-shell crab and crab salad sandwiches \u2014 because that\u2019s what he mostly goes after. In the winter months, I might do fresh mullet, snapper or grouper.<\/p>\n<p>\u201cIn 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.\u201d<\/p>\n<p>Williams-Sims\u2019 most popular items, the pies and chowder, now live on beyond Capt\u2019n Con\u2019s.<\/p>\n<p>Jolly Rogers &amp; The Captain\u2019s Pie Shoppe ($$), 239-878-6317, provides pie and chowder ordering information and posts the truck\u2019s location on Facebook. Delivers to Punta Gorda, Cape Coral, North Fort Myers, Matlacha and Pine Island. Look for the Jolly Rogers truck from 5 to 8 p.m. at Downtown Kava, 1009 Taylor St., Punta Gorda, on Saturday, Aug. 1, and for The Captain\u2019s Pie Shoppe pies at Salty Girls Island Caf\u00e9, 10700 Stringfellow Road, Suite 30, Bokeelia.<\/p>\n<p>FROM SERVICE TO SERVICE<\/p>\n<p>Fernando Pupo\u2018s Sergeant\u2019s Cuban Express is one of those food trucks that nails success by specializing in one food, then delivering the best version of it in town.<\/p>\n<p>Born in Miami, Pupo used his college degree to do government contract work in ops and logistics after 12 years in the U.S. Marines.<\/p>\n<p>When government work started drying up, he decided to build something of his own, inspired by his mother, Margarita, with whom he\u2019d planned to start the truck until her recent death.<\/p>\n<p>Sergeant\u2019s serves not only potent Cuban coffees but also a viral Cuban sandwich stuffed with tender, slow-roasted pork plus the usual ham, Swiss, pickles and mustard. There are Cuban pastries, too, but that sandwich is what\u2019s drawing customers.<\/p>\n<p>David Mone of North Port stopped by one day to get his wife, Maria, two of them \u2014 one for lunch, another for a snack later.<\/p>\n<p>\u201cAs far as my wife\u2019s concerned, this is the best Cuban sandwich around,\u201d David said.<\/p>\n<p>Sergeant\u2019s Cuban Express ($-$$), 941-300-0471, is often open 9:30 or 10 a.m. to 2 p.m., at Lowe\u2019s, 5601 Tuscola Boulevard, North Port. Check its schedule on Facebook.<\/p>\n","protected":false},"excerpt":{"rendered":"Young eatery owners today aren\u2019t becoming their parents. No matter how large a legacy they carry, it makes&hellip;\n","protected":false},"author":2,"featured_media":357562,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[14],"tags":[209,211,210,145942],"class_list":["post-357561","post","type-post","status-publish","format-standard","has-post-thumbnail","category-cape-coral","tag-cape-coral","tag-cape-coral-headlines","tag-cape-coral-news","tag-cape-haze-convenience-store"],"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts\/357561","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/comments?post=357561"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts\/357561\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/media\/357562"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/media?parent=357561"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/categories?post=357561"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/tags?post=357561"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}