Chokoloskee Bay is a roughly 10-mile long coastal bay located in southwest Florida, tucked between Everglades City and the Ten Thousand Islands archipelago. It serves as a primary gateway for paddling into the extensive mangrove maze of the Ten Thousand Islands National Wildlife Refuge and the Everglades National Park's Wilderness Waterway. The bay's open water faces directly onto the Gulf of Mexico, making paddling conditions subject to significant wind and strong tidal currents. Checking tide charts is strongly recommended, as tides will influence the timing and difficulty of trips; for routes leading into the backcountry, paddling downstream is advised on an outgoing tide to utilize the tidal flow. The area is characterized by a mix of open water, deep tidal channels, and mangrove shorelines.

Primary public launch points include the Gulf Coast Visitor Center in Everglades City, the causeway along Smallwood Drive on Chokoloskee Island, and facilities like Chokoloskee Island Park & Marina and Glades Haven RV Park. The Gulf Coast Visitor Center is a common starting point for ranger-guided tours and multi-day wilderness trips. Paddlers should be prepared for strenuous conditions, as the bay is exposed, with potential for strong winds and a notable fetch. Powerboat and airboat traffic is abundant, requiring caution, especially when crossing marked channels. The paddling difficulty is generally considered moderate to difficult due to these combined factors of wind, tide, and boat traffic.

The bay provides access to several established routes. A popular day trip is the paddle trail from Chokoloskee Bay to Sandfly Island. For multi-day expeditions, paddlers can follow the marked channels south from the bay into the Wilderness Waterway, with destinations like Sunday Bay Chickee and Sweetwater Bay Chickee. The best time for paddling is during the dry season from November through April, with December through March being ideal due to cooler temperatures, lower humidity, and fewer mosquitoes. A wilderness permit is required for all overnight camping, which can be reserved in advance. Wildlife viewing is a key attraction, with opportunities to see a variety of birds, fish, and other animals along the mangrove edges.