Man of War Harbor is a coastal anchorage located on the north side of Key West, Florida, providing a sheltered area for paddlers relative to the more exposed surrounding waters. The harbor is bordered by Wisteria Island and Fleming Key, with the area north of Wisteria Island and behind its shoals noted for offering calmer conditions. Access for launching and landing is primarily via shorelines, as the harbor is a designated anchorage for larger vessels; there is no formal public boat ramp. A water taxi service operates to and from the harbor, reachable on VHF Channel 68, which can be used for shuttle logistics. The overall character is that of a busy, working anchorage close to a major tourist destination, with Key West Bight Marina and the Historic Seaport a short distance away.

Paddlers must be highly attentive to significant boat traffic, including large tour boats that generate substantial wakes, especially when transiting the marked channels leading into the harbor. The area east of Wisteria Island is noted to be more exposed to powerboat wakes. Wind is a major factor, with forecasts frequently indicating strong winds and significant gusts, requiring experienced paddling skills. While the harbor offers a lee from the wind compared to open water, conditions can still be challenging. The water temperature is consistently warm, with forecasts in August showing temperatures exceeding 31°C (88°F). Portuguese Man of War jellyfish are present in the adjacent waters, which is the likely namesake for the harbor and represents a stinging hazard.

From Man of War Harbor, paddlers can access numerous Key West attractions via short crossings. Destinations within reach include Mallory Square, Duval Street, the Southernmost Point buoy, Fort Zachary Taylor State Park, and the Historic Seaport. These crossings will involve navigating active channels with consistent boat traffic. The harbor itself provides views of Fleming Key, where military operations are sometimes conducted. Given the urban, high-traffic environment and exposure to wind and waves, this area is best suited for confident paddlers with solid boat-handling skills in dynamic conditions.