Last Updated: October 24, 2025

Nestled at the southern tip of Pine Island in the laid-back community of St. James City, the Ragged Ass Saloon first opened its doors in 1954 and quickly became one of Southwest Florida’s favorite “Old Florida” waterfront hangouts. Located on the Monroe Canal, this open-air tiki-hut bar welcomed boaters, bikers, and locals seeking cold drinks, live music, and the kind of unhurried charm that defines island life.

The Ragged Ass Saloon was more than a bar — it was a way of life. With easy dock access, an open-air deck, and live entertainment under the palms, it drew visitors from Sanibel, Captiva, and Fort Myers. A 2016 News-Press review captured its vibe perfectly: pizza topped with green olives and banana peppers, pork wings, live music, and a loyal crowd arriving by boat or bike.

Before Hurricane Ian, the Ragged Ass represented the best of Pine Island’s personality — independent, unpretentious, and always welcoming. It wasn’t fancy, but it was unforgettable — the kind of place where dolphins passed through the canal, neighbors gathered for sunset beers, and island bands filled the air with tropical tunes.

When Hurricane Ian struck Southwest Florida in September 2022, Pine Island and its waterfront businesses were hit especially hard. The Ragged Ass Saloon suffered severe structural damage and ultimately closed permanently, marking the end of an era. For many longtime residents and seasonal visitors, its loss symbolized the profound impact of Ian on local culture, hospitality, and everyday island living.

But island resilience runs deep. In true Florida Gulf Coast fashion, the story doesn’t end there. According to Channel 3 and Yahoo News reports, the historic Ragged Ass Saloon property is now being reborn as a brand-new waterfront restaurant — a modern venue that honors the same Monroe Canal location while introducing a fresh dining experience.

The transformation reflects the broader recovery and revival of Pine Island. As new owners rebuild along the water, this reimagined restaurant will once again give visitors a place to dock their boats, enjoy a meal, and soak in the easygoing Old Florida spirit that made the original famous.

For visitors exploring St. James City, this new chapter offers the perfect excuse to revisit a classic spot and see how the island continues to evolve. For homebuyers and real-estate investors looking at Pine Island waterfront property, the rebirth of the Ragged Ass site is a tangible reminder of how communities adapt, rebuild, and thrive after a major storm.

As the new restaurant takes shape, the Monroe Canal remains as inviting as ever — lined with mangroves, fishing boats, and pastel-colored homes that capture the best of coastal Southwest Florida living. Whether you remember the old tiki bar or are discovering this corner of paradise for the first time, the Ragged Ass Saloon continues to embody the area’s enduring charm: resilience, character, and connection to the sea.

Visitors planning a trip to Pine Island should check local listings for updates on the restaurant’s official opening, dock access, and live-music schedule. Pair your stop with a stroll through St. James City’s art galleries, a visit to the Monroe Canal Marina, or a sunset boat ride along the Pine Island Sound.

While the original tiki-bar days are gone, the spirit of the Ragged Ass Saloon lives on — refreshed, rebuilt, and ready to welcome a new generation to Pine Island’s waterfront.