Estero Bay is a large, open coastal bay in southwest Florida, characterized by shallow, clear saltwater and extensive mangrove shorelines. The bay is a designated paddling trail, with the nine-mile route considered suitable for intermediate paddlers comfortable with open water conditions. The primary paddling experience involves navigating from the sheltered tributaries into the exposed bay, where wind can be a significant factor. The bay's western side is bordered by barrier islands, including Lovers Key State Park and Big Hickory Island, which provide some protection but also create long, open fetches where wind-driven waves can build.

Key launch points for accessing the bay include the Estero River via Estero River Outfitters or Koreshan State Park, and the Imperial River via Riverside Park, Depot Park, or the Imperial Boat Ramp in Bonita Springs. From Koreshan State Park, it is approximately 4.5 miles down the Estero River to reach the bay. The bay itself offers a mix of environments, from the maze-like mangrove tunnels and backwaters of Hell Peckney Bay, which are sheltered from boat traffic, to open crossings to destinations like Mound Key, an archaeological island located about 4.5 miles west of Koreshan. Paddlers must be prepared for powerboat traffic, especially near channels and passes, and should exercise caution when crossing these busier waterways. The Estero River, while a beginner-friendly spring-fed tidal river, has noted safety concerns regarding boat traffic once it approaches the bay near the West Bay Club area.

Tidal currents are a primary consideration for trip planning, as the bay and its tributaries are tidal. Guided tours and rental operations schedule departures around tidal conditions. Paddling against a strong tidal current, especially when combined with wind, can be challenging. The water is generally clear and shallow in many areas, allowing for visibility of marine life like starfish and sand dollars. Wildlife sightings commonly include dolphins, manatees, and a wide variety of birds. The area has historical significance, featuring sites like the Koreshan State Historic Site and the Calusa shell middens on Mound Key. Facilities are available at state parks and local outfitters, which offer rentals, launches, and guided trips. For a first venture into the complex mangrove backwaters, joining a guided tour is recommended.