Assawoman Bay is a coastal saltwater bay located along the Delaware and Maryland border, connected to the larger inland bays system. For paddlers, the primary access is through its southern portion, known as Little Assawoman Bay, and the connecting Assawoman Canal. The bay is a broad, open water body with significant exposure to wind, making conditions highly dependent on weather. Paddlers must be mindful of wind and the resulting wave fetch across the open water, as well as motorboat traffic, particularly in marked channels. The area is a brackish water estuary and saltmarsh, featuring long stretches of marsh grasses and pine woods along its shores.

Several public launch sites provide access. In Delaware, key launches include the Assawoman Recreation Area within Fenwick Island State Park, which requires a daily park entry fee, and the free launches at Sassafras Landing, Strawberry Landing, and Mulberry Landing within the Assawoman Wildlife Area. The Assawoman Canal, a four-mile long, dredged waterway connecting Indian River Bay to Little Assawoman Bay, offers protected paddling with launches at the Assawoman Canal Trailhead on New Road and the Guy Street boat ramp below the Jefferson Bridge. The canal is narrow, calm, and lined with trees, providing shade and a different experience from the open bay.

Tides significantly influence paddling conditions, with the nearest reference tide tables being for Indian River Inlet. Currents are present, notably stronger at the northern end of the Assawoman Canal, so planning a trip with the tide is advised. The open bay features salt marsh islands and numerous small creeks and cuts within the wildlife area, ideal for exploration. Wildlife is abundant, with opportunities to see various bird species. The overall experience ranges from exposed, wind-affected paddling in the open bay to calm, sheltered travel in the canal and marsh creeks. Paddlers should always be prepared for changing weather, wind, and tides, and remain vigilant for boat traffic.