Escape to Captiva Island

A visitor gets a delightful taste of one of Southwest Florida’s most treasured destinations

From left: Chambless takes in the view at her hotel, South Seas Island Resort; a sunny lunch at South Seas' poolside restaurant, The Pointe; the Old Captiva House restaurant.

Along the Southwest Florida coast, sunseekers have sought out the islands, beaches, and neighborhoods of Fort Myers for generations. Blissful discoveries are abundant, from endless white-sand shores and peaceful, mangrove-lined channels to lively hubs for eating, drinking, and adventuring on land. Among the area’s many barrier islands, the secluded Captiva Island is known for having some of Florida’s most pristine beaches, as well as a small but charming village full of character. For a firsthand experience of this Gulf of Mexico gem, Garden & Gun partnered with Charleston, South Carolina–based lifestyle blogger Kristin Chambless, who eagerly planned a midwinter escape to the warm, palm-studded locale.

Captiva is easily accessed by car—a scenic journey in itself, taking travelers over the Sanibel Causeway and through the beautiful island of Sanibel. Once on Captiva Drive, visitors are greeted with the sight of flowering bougainvillea and other tropical blooms, as well as the charming (often pastel-painted) shops and restaurants that populate the island’s heart. 

Vessels docked at one of South Seas' marinas.

Upon arrival, Chambless checked in to South Seas Island Resort, a chic retreat with a classic Old Florida feel on the northern tip of the island. Surrounded by a 330-acre wildlife preserve, the resort grants access to some of the island’s finest natural wonders, be it dolphins cresting along the beach, manatees coasting through the backwaters, or excellent shell hunting on two and a half miles of private beach. South Seas offers a slew of desirable amenities on-site—including three glistening pools, world-class golf and tennis facilities, and a spa and fitness center—as well as bike, golf cart, and boat rentals to help guests better explore the rest of the island. 

While natural beauty may be what draws visitors to Captiva, the island’s dining scene is not to be overlooked. During her trip, Chambless visited some of Captiva’s most popular spots, with the highlight being Old Captiva House. “A restaurant so nice, we went twice!” she says with a laugh. “Captiva House is everything I look for—and love—when I travel.” Located at ’Tween Waters Island Resort & Spa, a historic inn opened in 1931, the recently reimagined restaurant is listed on the National Register of Historic Places, with much of its original architecture intact. The menu features some of the most elevated cuisine on the island, including dishes such as handmade lobster ravioli in tomato-ginger broth, cioppino (or fisherman’s stew) studded with fresh-caught delicacies, and pan-seared branzino on a bed of mushroom risotto.

From left: South Seas' on-site convenience shop, Ships Store; Chambless enjoys the Gulf breeze from her balcony; classic Old Florida architecture on the South Seas property.

For breakfast, the iconic Keylime Bistro was a must-stop. Known for its bright, multicolored paint job and lively atmosphere, the restaurant is nestled in the heart of the island’s historic district. “Any place that serves breakfast until 2:00 p.m. is my kind of place,” says Chambless, who was charmed by the extensive menu of diner-style standards. Back at South Seas, a lazy day poolside is enhanced by lunch at The Pointe, where a covered patio and plentiful deck tables offer respite from the sun. Between dips, Chambless enjoyed a Cobb salad (and a side of fries for good measure), paired with a view of the Pine Island Sound from the pool deck. Just beyond the dining area, the resort’s private beach beckons, along with complimentary lounge chairs and umbrellas reserved for hotel guests. 

A blue-sky afternoon at the South Seas dock.

However travelers spend their evening—indulging in a white-tablecloth meal or strolling the beach barefoot at sunset—a drink or a late-night snack at RC Otter’s makes for the perfect finale. “We stopped in to RC Otter’s after dinner for a nightcap and were greeted with live music and dancing,” Chambless says. “It’s a local favorite, to be sure.” Embodying Captiva’s eclectic spirit, the restaurant is another rainbow-hued space, sure to delight patrons of all ages. And for those looking to experience more of the island’s quirkier side, nothing can compete with the Bubble Room. “We heard from multiple sources that the Bubble Room was not to be missed,” says Chambless of the institution, founded in 1979. A self-described “multi-theme” restaurant, the Bubble Room is chock-full of everything from Christmas decor to cinema memorabilia to toys and collector’s items several generations old. Ostentatious interior aside, the restaurant may be best known for its generously sliced cakes, created daily in an on-site bakery. 

Together, the trip’s activities amounted to a getaway Chambless won’t soon forget. “Captiva Island was such a picturesque escape,” she says. “It really embodied that Old Florida charm I love.” To discover even more on this pint-size island and in its surrounding region, and to plan your own Southwest Florida trip, visit