The San Sebastian River runs along the western edge of St. Augustine's downtown, forming a natural boundary between the historic district and the US-1 corridor before emptying into the Matanzas River near the Bridge of Lions. It is one of the lesser-known waterways in the St. Augustine area but an important one ecologically, historically, and recreationally. The river flows north to south through the city's western neighborhoods, passing beneath the US-1 bridge and feeding into the broader estuary system that characterizes coastal St. Augustine. The San Sebastian and its surrounding wetlands provide habitat for wading birds, dolphins that follow fish into the river from the Matanzas, manatees in warmer months, and a variety of fish species that make it productive for inshore fishing. San Sebastian Winery sits on the bank of the San Sebastian River, occupying a historic building that was once part of the Florida East Coast Railway operations. The winery offers free tours, tastings, and rooftop views across the river and the surrounding historic district - making it one of the most unusual and pleasant wine tasting experiences in Florida. The building's connection to Flagler's railroad history adds another layer to a visit. The river is navigable by kayak and small boat and can be paddled from several access points along its length. The western view of downtown St. Augustine from the San Sebastian River offers a completely different perspective on the city than the bayfront view most visitors know - the backs of historic buildings, the train depot, and the skyline seen from the industrial west side rather than the manicured bayfront. Fishing along the San Sebastian River targets redfish, trout, flounder, and sheepshead. The calmer waters and shallower depths make it particularly accessible for wade fishing and kayak fishing compared to the open Matanzas Bay. Highlights: Western boundary waterway of historic downtown St. Augustine San Sebastian Winery sits on the riverbank - free tours and tastings Kayak and small boat access from multiple points Excellent inshore fishing - redfish, trout, flounder, sheepshead Dolphin and manatee sightings common Connects to the Matanzas River and broader estuary system Unique westside perspective on downtown St. Augustine Historic Florida East Coast Railway building on the banks Less crowded alternative to Matanzas Bay for paddlers