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Boca Grande, just 10 miles across the water from Pine Island but an hour and a half drive from Fort Myers, is perhaps Lee County’s best-kept secret. The town itself is often overlooked for its waters—the Boca Grande Pass is one of the best local spots for tarpon fishing. In fact, if you search for what to do in the area you’ll mostly turn up fishing guides. But the town of Boca Grande itself is well worth a visit.
I drove up on a recent Saturday afternoon, an unseasonably warm day where the humidity left me sweating the instant I stepped out of the car. The town of Boca Grande is set on Gasparilla Island, a barrier island off the coast of Charlotte Harbor. Along the beaches, I’m sure there must have been a breeze, but in the historic center of town the air was as hot and still as the inside of a kiln.
The heat aside, setting foot in Boca Grande is like stepping on the set of a Ralph Lauren photo shoot. The streets are immaculately clean, the buildings are painted in tasteful white and navy, and the people are dressed in pastels and pressed khakis. Tortoiseshell sunglasses are de rigueur. The color palette trends toward tasteful Americana with a touch of Lilly Pulitzer tropical flair. I realized right away that Boca Grande is an island paradise for a certain kind of elite, the sort that summers on Martha’s Vineyard and winters, well, in Boca Grande. There’s a feeling of well-heeled exclusivity that’s different from Sanibel with its fondness for native plants and wild places or even slick, sophisticated Naples. Boca Grande says, “My ancestors arrived on the Mayflower, my children go to Ivy League schools and my name has probably appeared on your voting ballot.” (The Bushes, among others, vacation here.)
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I started my visit with lunch at the Loose Caboose, set in the historic train depot, a casual spot with tarpons mounted on the wall. The interior was mercifully air-conditioned, but I opted to sit outside, suffering the blazing heat in order to watch the parade of golf carts. Parts of Boca Grande are off-limits to gas-powered vehicles, and golf carts are the only way to get around. Make no mistake: These aren’t the carts you see on public courses or the kind that tool around retirement communities. These are statement vehicles, each with a custom paint job, top-of-the- line additions and a pure-bred dog perched on the back seat. As I ate my crab cakes, I eavesdropped on the couple behind me—the woman in a pink polo shirt and straw hat, the man in designer shades—as they discussed equity investments over club sandwiches. I smiled. The scene was just right.
After lunch I strolled through town, admiring the houses along the street. They were picture-perfect beach cottages, many with white trim and wood siding, the kind you’d see in Southern Living. Bright pink bougainvillea spilled over white picket fences, and everything exuded good taste. In some parts of the Gulfshore, I’ve noticed, people go to great lengths to conceal their status. You probably know them: the men who wear old swim trunks to dinner while they sit on $10 million in the bank. Boca Grande isn’t like that. It’s unapologetic about its wealth, its beauty and its fine breeding. I found it refreshing.
Eventually, I reached Banyan Street, a stretch of road bordered by tall banyan trees on both sides (see above at right). Their massive branches grew together to form a canopy that shaded the path. On this particular day chairs had been set up for a wedding, and somewhere hidden behind the trunks of the trees a vocalist practiced Ave Maria while a string quartet rehearsed. Guests in chic, pastel-colored ensembles streamed in. The effect was stunning. Carefully crafted, I’m sure, but Boca Grande is one place that makes no amends about the good thing it’s got going.
If you go …
• Boca Grande has a trio of famous eateries—The Pink Elephant (491 Bayou St.), The Temptation (350 Park Ave.) and the Loose Caboose (433 W. Fourth St.). They each offer a selection of local seafood in a relaxed island setting. If you wind up at the Caboose, be sure to order the crab cakes.
• To see the famous waters of the Boca Grande Pass without getting seasick, head to the historic lighthouse at the very tip of the island. The beach is beautiful in this state park, but there’s no swimming because of the dangerous currents.
• Boca Grande has an air of tropical gentility, and if you don’t want to look like a tourist you’ll need to dress the part. Bring your best resort wear, and leave the cutoffs at home.