If you're planning a Chesapeake Bay sailing charter, one of the first decisions you'll face is whether to sail from Annapolis or Maryland's Eastern Shore. While Annapolis is often the best-known sailing destination on the Bay, a Rock Hall sailing charter offers a very different experience—one defined by open water, quieter surroundings, and a more authentic connection to the Chesapeake.

Both locations share the same Bay, but once you're on the water, the differences become clear.

The Chesapeake Bay is one of the East Coast’s best destinations for relaxing day trips, scenic waterfront towns, sailing adventures, fresh seafood, and outdoor experiences. Whether you’re planning a romantic getaway, a family outing, or simply looking for a break from city life, the Bay offers countless ways to spend a memorable day on the water. From private sailing charters to historic towns and island escapes, here are five of the best things to do on the Chesapeake Bay.

Sailing and exploring the Chester River on the Northern Chesapeake Bay