Weekends on the Water: Annapolis, Maryland

Join CBM for a weekend exploration around Annapolis, Maryland. Sponsored by Pocket Yacht.

Fast facts

  • Located where the Bay meets the Severn River, just south of the Chesapeake Bay Bridge
  • Established in 1649 and incorporated as a city in 1708
  • One of the first cities to be named a National Historic Landmark District
  • Home of the world’s original in-water sailboat and powerboat shows, held each October
Video by Zion Pyatt.

Captain Kate is onboard the Cutwater C-288 Coupe sold by the Pocket Yacht Company.

What Makes It Unique

For most people who love the Bay, a visit to Annapolis is a given. All those boats, restaurants, shops and history—what’s not to love? Yet many boaters leave their vessels at home, opting instead to pile the family into the car and wrestle the weekend traffic so they can hunt for a good parking space at City Dock to start the fun. Then a few hours later, it’s time to head home. Why? Because the thought of navigating the busy waters of Annapolis Harbor is intimidating. But that’s a mistake, because America’s Sailing Capital is even better when you visit by water, as it was originally intended.

Even if you’ve made the road trip to Annapolis, it’s key to understand how the city is laid out if you are arriving by water. The Eastport neighborhood lies snugged between Back Creek and Spa Creek, just inside the mouth of the Severn River. West Annapolis stretches farther up the Severn. Historic downtown Annapolis and the U.S. Naval Academy lie on the north side of Spa Creek. The city’s largest marinas, as well most of its service and repair yards, lie along both sides of Back Creek. All of this is connected by water taxis or can be accessed with your dinghy, which you can tie up at any number of dinghy landings throughout the two creeks. READ MORE HERE