Beyond the turquoise waters and wide stretches of sugary sand, the charm of Boca Grande is sealed by the porched and columned facades that convey the bygone days of Old Florida—and its charming Southern drawl.
Sandy Stilwell Youngquist has been enchanted by the quaint town at the end of Gasparilla Island since she strolled under the boughs of Banyan Street, near the Downtown Boca Grande Historic District, in her early 20s (she says the tree-lined way is the perfect spot for photos—the street’s so scenic couples often choose it to exchange “I do’s”).
It’s no surprise the Captiva Island queen—who owns an inn, five restaurants and a shopping center on the nearby barrier island—chose Boca Grande to expand her epicurean empire in late 2022. A love for preservation and exalting Old Florida is at the heart of Sandy’s ventures.
On November 1, weeks after Hurricane Ian wreaked havoc, she opened her second Keylime Bistro in Boca Grande’s old train depot, which is listed on the National Register of Historic Places. (Look out for her third locale in the new terminal of Southwest Florida International Airport in 2025.)
“To this day, it’s a breath of fresh air when I go over the bridge in my car or pull up to the docks in our boat—it feels like stepping back in time to a place that is not overdeveloped or overcommercialized,” Sandy says, emphasizing how Boca Grande offers a perfect blend of nature, small businesses and beautiful homes.
She wants others to discover the town’s appeal and how it’s possible for an area with blocks upon blocks of multimillion-dollar estates to remain unpretentious. Much of it starts with the people who frequent the island, a quiet-luxury crowd that likes to drink their sweet tea rather than spill it and ride around on golf carts before a few rounds of backgammon with a Gulf-inspired Boca Punch in hand.
No visit to the town is complete without seeing one of Sandy’s favorite spots, The Gasparilla Inn & Club, notably a longtime winter retreat for the Bush family. The restaurateur urges venturing into the striking Colonial Revival main building on Palm Avenue and booking lunch or dinner at one of the inn’s iconic dining venues, such as The Pink Elephant—called “The Pink” by locals.
In a time and place where anything goes sartorially, the inn clings to tradition, with a formal dress code that requires whites on the croquet lawns and collars and/or jackets throughout most other spaces. Sandy recalls a few years back when she and her husband, Tim, invited friends to celebrate the Kentucky Derby at the inn. While Boca Grande’s ‘season’ was long over the first weekend in May, they dressed to the nines to take in all the pre-race coverage at main floor lounge BZ’s. The inn indulges Sandy’s penchant for history and Old Florida charm. “It’s beautiful and exudes elegance with its white rattan furniture, pinks, greens and turquoise,” she says. “It’s very reminiscent of Southern hospitality.”
As she ventures deeper into the island, Sandy loves how innately walkable—and bike- and golf-cart- friendly—the community is (rental spots abound, but there’s not a single gas station). “You can park your car and bike all over the island,” she says.
Her favorite trail, the Boca Grande Bike Path, transformed the old railroad tracks, dating from the Gilded Age, into a verdant rail-trail that flows into Gasparilla Island State Park, home to the Port Boca Grande Lighthouse and Museum (a unique, two-story, square-shaped, shingled structure with a light nestled in a widow’s walk).
You can ride the trail to and from the historic train station that’s now home to Sandy’s Keylime Bistro and Loose Caboose ice cream parlor. The depot, which ushered industrialists and winter residents until its closure in 1958, still marks the heart of Boca Grande. “You can shop, you can dine; you can even bring a picnic. But to me, the dining is half the fun,” Sandy says.
Aside from her place (known for crab cake benedicts, grouper sandwiches and cocktails), she cites a tiny spot called The Temptation Restaurant that has a great wine list and a sign urging “Please, no profanity.” The bar Miller’s Dockside at Boca Grande Marina also draws her and Tim when they dock their boat after a day of exploring. The couple often opts to spend the night aboard their vessel, and Miller’s provides a lively scene in the evenings.
When it comes to dressing for days out (or picking up a souvenir), Sandy mines hidden gems. Sunsets of Boca Grande is her stop for cute handbags and resort wear; or, she’ll head to The Palm on Park – A Lilly Pulitzer Signature Store to channel the preppy-pretty Florida look. She wouldn’t let you leave town before swinging by the 1916 emporium Fugate’s and the town’s oldest marina, Whidden’s, which covers all your bait-and-tackle needs, along with offering a solid dose of local color via old photographs and artifacts.
& Club to The Palm on Park — A Lilly Pulitzer Signature Store, Boca Grande suits Sandy’s love of history and preppy-pretty Florida style.
Sandy delights in Boca Grande’s history and many singularities. Though the entrepreneur’s well- traveled through Gulf waters, she says there’s something special about witnessing the leaping silver-back tarpon that make the deepwater Boca Grande Pass renowned for sportfishing. She recalls springtime tournaments so packed with boats that you could hop from one deck to another, and likely be welcomed aboard by each new host.
In many ways, Boca Grande is ideal for mariners, and that speaks to the core of this ocean-loving gal. Only boaters can access the island’s best beach—a crystal-clear swatch surrounding a sandbar at the former rail bridge on the island’s north side. It’s only fitting the best beach evokes nostalgia in a town that celebrates its cherished past.
Photography by Anna Nguyen
