The best way to explore the bay on a chartered sailboat is from the heart of the city.. In Short With a fleet of 19 sailboats available for both skippered and bareboat charters, there's something for every sailor or sailing wannabe. The 23-foot Sonar is a swift little racing sloop--great for learning. The Hunter 310 is a 31-footer with a full galley that sleeps six. Large groups (up to 20 people) can charter a 43-foot cruising ketch for a sunset cruise out to Fort McHenry. For a half day on the Chesapeake, launch into the urban waters near Canton, explore the nooks of the Inner Harbor then venture out near the mouth of the bay.