Chesapeake Bay Boating

Whether you’re local to the Chesapeake Bay area or just visiting, one of the best ways to experience the region and the lifestyle is to get out on the water.

The Chesapeake Bay, immortalized by countless writers, artists, sailors and naturalists, is a truly magical destination along the coastal shores of the United States. It is the largest estuary with the most coastline of any other bay in the U.S.  It has more than 150 rivers and streams which feed its rich grounds and as much variety along its shores as any cruiser would wish to find.

Cruising The Chesapeake Bay

Cruising boaters can select from many boating destinations, from Maryland to Virginia, there’s plenty to see and do. Check out Chesapeake Bay cruising destinations here and cruising guides here.

Chesapeake Bay Charter Fishing

If you don’t captain your own boat there are plenty of fishing charter boats that operate throughout the Chesapeake Bay region. If you want to ensure that you have a great day on the water, taking a charter is a wonderful option. Charter Captains know where to find the fish and the best ways to catch them. Find Chesapeake Bay fishing charters here.

Paddling The Chesapeake Bay

The Chesapeake Bay is full of shallow, protected waters which make it perfect for canoeing, kayaking and paddle boarding. By exploring the bay in these smaller crafts it allows you to really get up close to nature and navigate through areas that larger boats are unable to. Find more about paddling the bay here.

Racing on The Bay

The Chesapeake Bay also offers a wealth of sailing and motorboat racing opportunities. The Chesapeake Bay Yacht Racing Association helps organize and manage races in more than 50 different classes of boats. Find out more about racing on the Chesapeake Bay here.

Boating Courses and Schools

If you’re interested in learning how to operate a boat or to increase your boating skills there are plenty of certified boating schools and classes in the region. Courses are available to teach basic boating skills, sailing and navigating. Check out boating schools here.


The Chesapeake Bay region is filled with marinas. This makes having a boat or visiting by boat easy since there are countless of places to dock. Most marinas provide a combination of boat slips for locals who keep their boat there long term and also for transients who only need to dock for a night or two. Find a list of Chesapeake Bay marinas here.