Longtime Captiva Island entrepreneur Sandy Stilwell Youngquist isn’t a crier—not even after seeing her properties post-Ian. “I was stunned more than anything,” she says. “Sometimes, I’d get home and just think about the huge undertaking of work ahead of me and pray to God to give me strength and help me make the right choices.” One of the hardest dilemmas she faced: How could she keep her staff employed when all five of her restaurants and her Captiva Island Inn were shuttered and in need of major repairs? But, she did it—keeping everyone who wanted to work, her employees say.
Meanwhile, a well-timed endeavor equipped the entrepreneur to weather the storm. A month after Ian, Sandy debuted a second location for her Keylime Bistro. The restaurant is famed for its titular dessert, with its two levels of decadence that contain a custard-like base and fluffy top layer over a dense, crunchy crust, with sweet and tart swirls of raspberry and Key lime sauces. The new locale is a few islands north in Boca Grande’s former Loose Caboose location. Charmed by the building’s historic grandeur and communal ties, Sandy jumped at the chance to buy the restaurant and ice cream parlor on the tail end of the town’s circa-1910 railroad depot.
She kept the creamery, with the Loose Caboose Ice Cream Shoppe connected to Keylime Bistro Boca Grande. If there’s something Sandy—who has lived in Southwest Florida most of her life—knows how to do well, it’s capturing the wind-in-hair, toes-in-sand, laidback vibe diners seek on a beach vacation. When she bought the Captiva restaurant, she took the booths into the parking lot and beat them with chains to erase the formality of the former locale. She painted the space pastel purple, blue and green to channel the happy spirit of the islands. The Boca Grande restaurant runs much like the original on Captiva, with its worry-free beachy style and the sea breeze sweeping through the room.
Dining at Keylime Bistro is what Sandy calls “eclectic with a whimsical flair.” Chef Nehru Williams—who has worked at The Sandals Resort in Jamaica, Captiva mainstay The Bubble Room and Sandy’s R.C. Otter’s—focuses on traditional Floribbean flavors, with macadamia-crusted mahi, grouper sandwiches and tropical versions of traditional dishes, like the marinara-based paella that eschews saffron and folds in scallops, calamari and sausage. Daily live music fills the patio, shaded with big, light-strung umbrellas. Inside, she added an L-shaped bar splashed with Keylime Bistro trademark hues. Sandy left the train mural and memorabilia as a meeting of new and old. The space seems destined to entertain, with its bright and nautical touches. It evokes what Sandy fell in love with about Boca Grande: the air of elegance you find all over the island town.
Built up by the Charlotte Harbor and Northern Railway in the early 1900s and subsequently discovered by the Rockefellers, du Ponts, J.P Morgan and their ilk, Boca Grande and its legendary tarpon fishing made for a rich man’s playground. The grand Gasparilla Inn spurred the town’s reputation as a prestigious getaway.
Sandy and her husband, Tim, often boated to Gasparilla Island with friends for breakfast or lunch at “the Caboose,” as locals called the restaurant. The locale’s homemade ice cream was so celebrated that actress Katharine Hepburn once pinned an appreciative note to the shop’s bulletin board.
The same day she heard the Caboose was for sale, Sandy made the trip; she made an offer the next day. Then came Ian. “I was due to close on the Loose Caboose, ironically, the day Hurricane Ian hit, but my insurance company wouldn’t sign off on underwriting it with a hurricane out there,” Sandy says. “I had to look hard after the storm to see if it was a wise decision.” It turned out to be her lifeboat in the swell of devastation.
Sandy boated back to Captiva two days after the storm to pick up her son, Erik Brown, who had stayed at her home there. She informed employees at all six businesses that she’d pay them to help with salvage and clean-up operations on the island. Before the Sanibel bridge was repaired, she and her family ran three boats, including one she captained from her home at St. Charles Yacht Club in south Fort Myers. As other job opportunities opened, she offered staffers an “out” to take better-paying positions to support themselves and their families until they could return to their old Captiva gigs.
Boca Grande, too, had its hurricane woes: Most vacation rentals will likely be off-market until November—a full year after Sandy opened her restaurant. But, by February, the island’s beaches were open, and old Captiva friends were showing up on the island. “We see many of our regulars in Boca Grande now that word is getting out,” Sandy says. The second Keylime proved so successful that Sandy is considering creating more outposts, with a small-scale version at Southwest Florida International Airport next on her list.
And, she’s not staying quiet on Captiva, either. While she waits for her hometown operations to be in working order, Sandy set up a food truck, Rico Suave’s Mexican Cuisine on the Go, where the team serves the Mexican fare regulars were used to enjoying at Cantina Captiva, which is still undergoing repairs. “I’m still here and resilient as ever,” she says. She expects all of her restaurants to be back by September.
Captiva Island Inn is another story, however. Of the 10 historic cottages—dating back to the ’50s—all but two had to be torn down. “I had to emotionally get over losing the cottages, but in the long run, it will be better,” Sandy says. She’s looking to rebuild and fully reopen the Inn by the time season rolls around in 2024.
As much as she loves Boca Grande, her heart is in Captiva, where she opened the inn in 1999. “Captiva has always been so magical to me,” she says.
