Downtown Naples
Since the 1950s, Fifth Avenue South and Third Street South have been the center of Naples identity — a blend of seaside elegance and small-town charm. Early visitors arrived by boat at the Naples Pier, trading with the Seminole long before boutique storefronts and fine restaurants lined the sidewalks. The district’s architecture preserves that legacy of understated luxury, where history meets high style.
In recent years, the city’s cultural core has expanded to include the Naples Design District. This creative corridor, known for its artisan studios, galleries and modern dining spots captures Naples’ evolution from a quiet fishing village to one of the Gulf Coast’s most sophisticated destinations.
Downtown Bonita Springs
Old 41 Road has been the center of Bonita Springs for years and has never been afraid of transformation. In the 1930s, visitors flocked to the Everglades Wonder Gardens, where flamingos and alligators basked in lush greenery. Almost a century later, the reimagined Wonder Gardens remains a centerpiece of the town — honoring the past while serving as a modern botanical and wildlife attraction.
Nearby, the historic Shangri-La Hotel still evokes Bonita’s early reputation for health and hospitality. Around it, a new era of vitality thrives in the preserved buildings, which have been transformed into niche restaurants, breweries and cocktail lounges. Riverside Park is home to concerts, festivals and community groups, while new ventures, such as Sugarshack Downtown, feature live music, craft beer and a welcoming, hometown vibe.
Fort Myers Historic River District
Fort Myers’ Historic River District reflects a rare success story — a downtown saved from decline through preservation and pride. Once overshadowed by suburban growth, its century-old buildings have become home to restaurants, galleries and festivals.
The Edison & Ford Winter Estates helped spark that revival — the 1915 vaudeville house transformed into The Florida Repertory Theatre, the old federal building became an art center and restaurants like The Veranda tell a story of endurance and reinvention. Today, the River District features rooftop lounges, outdoor markets and places like Bay Street Yard.
Downtown Punta Gorda
Founded in the 1800s, Punta Gorda preserves its roots as a harbor town with colorful murals that depict settlers, fishermen and the lives of early settlers. Marion Avenue’s lineup of eclectic shops and restaurants — including longtime favorites like The Perfect Caper and Celtic Ray Public House — echoes both history and evolution.
Across the river, Sunseeker Resort Charlotte Harbor draws new energy to the waterfront while honoring the town’s maritime legacy. Rooftop lounges at the Wyvern Hotel and the lively TT’s Tiki Bar at Four Points by Sheraton embrace life on the water. At the same time, Laishley Park and the surrounding trails provide opportunities to enjoy nature.
Boca Grande
Boca Grande began as the home of tarpon fishing, grand hotels and railroad tycoons escaping northern winters. The Gasparilla Inn, built in 1913, still conveys refined sophistication, and the old rail line now doubles as a scenic bike and golf cart path.
Today, the downtown area features shops, pastel architecture and canopy-lined streets. The Johann Fust Library, century-old churches and the Port Boca Grande Lighthouse & Museum reflect the rich history of Boca Grande. Today, visitors enjoy a timeless mix of elegance and unhurried charm.
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