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Sailing Chesapeake Bay

Chesapeake Bay stretches along the mid-Atlantic coast of the United States, welcoming sailors from all over the world year after year. The Bay has been a haven for watermen and recreational sailors for hundreds of years. It was on these shores that Jamestown was settled, and on the Bay’s tributaries, you’ll find some of the nation’s most famous cities, like Washington D.C. and Baltimore.
The Bay can roughly be divided into three sections: northern, central, and southern. Generally speaking, the Bay is surrounded by rural farmland and woodlands, with many creeks and shallow rivers awaiting exploration. Towns and ports of call along the Bay are small communities that once hosted watermen, with a few major cities and tourist stops along the way. Cruising the Bay is quiet and peaceful and away from it all, but when you want to go to town, there’s always something to see and do.
The northern bay is relatively narrow, with many creeks and rivers on each side. It is connected to the east to Delaware Bay via the man-made C&D Canal. Main ports in the area include Chesapeake City, Havre De Grace, Baltimore, and Rock Hall. The Chesapeake Bay Bridge separates the northern and central parts of the Bay. The Bridge connects Annapolis, the sailing capital of the Bay, if not the world, with the eastern shore of Maryland. On the northern and central Bay, you will find the eastern shore much more rural than the western shores. The farther you head south, the more rural everything becomes. Central Bay ports of call include Annapolis, St. Michaels, and Solomons.
The southern Bay includes all points south of the mouth of the Potomac River. The Potomac, the Bay’s largest tributary, is navigable northward to beyond Washington D.C. It also marks the Maryland/Virginia state line. Beyond this point, Chesapeake Bay becomes much wider and more rural. Several large rivers, including the Rappahannock, feed the Bay. Small fishing ports and marine centers, like Tangier Island and Deltaville, dot the banks. A little farther along, the major ports in the area include Yorktown, Hampton Roads, Norfolk, and Portsmouth.

Chesapeake Bay Sailing Tips

While you can enjoy sailing Chesapeake Bay year-round, the primary sailing seasons are the spring, summer, and fall. During the winter months, the Bay is subject to strong Nor’ easter storm systems, and the temperatures regularly dip below 30 degrees. Some creeks, especially in the northern Bay, ice over. Spring and autumn months are pleasant and mild, with fresh breezes and beautiful sailing. The cruising is excellent in summer, though the wind tends to be light and there is more thunderstorm activity. Summers can be hot and humid, but they provide an excellent time for beachcombing and swimming.
The Bay’s geography may deceive you into believing that you are cruising one of the more populated areas in the United States. However, the shores of Chesapeake Bay are charmingly rural. Large cities and ports are few and far between. The small towns ofter offer a relaxing getaway. Many marinas here provide courtesy cars for provisioning.
The many tributaries and winding creeks off of the Bay offer years of exploration. It is a true gunk-holers paradise.

Navigation on the Bay

Navigationally, the Bay is a fun and easy destination. The smaller tributaries and creeks are shallow, and care must always be exercised near the mouths of creeks and channels. Shoals are difficult to see, but channel markers and navigational charts are accurate here.
Sailing Chesapeake Bay usually involves navigating in and out of these tributaries to find the ports and anchorages that are protected and comfortable. Anchorages can be found in every nook and cranny along the creeks and rivers, where the woodlands and terrain provide protection from winds and seas.
As with any cruising, an eye must be kept on the weather. Cold fronts roll through regularly during spring and fall. Occasionally, a strong Nor’ easter or a tropical system affects the Bay.
The southern Bay and the mouth of the Potomac, in particular, are the most challenging areas. These are wide-open spaces. The rivers flowing into the Bay move a lot of water, and while the rivers are tidal for many miles inland, steep choppy seas can build up when wind opposes current. Plan crossing major rivers at minimum flow, or when the wind is favorable.
It should also be noted that a major shipping lane lies in the center of Chesapeake Bay. The ships travel north from the Chesapeake Bay Bridge-Tunnel, along the main channel, and onto the northern port in Baltimore. As recreational sailors, it’s best to give the ships a wide berth and remember that they are moving far faster than they appear to be.
Chesapeake Bay remains a large fishery. You will see many watermen plying these waters, setting their traps and hunting their prey. Blue crab and oysters are the primary targets. During the season, you will see oyster dredges working the rivers slowly, and you will see many crab pots. These floats are attached to the trap on the seafloor, and the watermen pull them up to harvest their crabs. In the meantime, they present an exciting navigational challenge: zig-zag your way through them without fouling your propeller. Marked channels are usually clear, but a constant watch is required.

Best Bay Marinas and Ports

Northern Bay

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If you’re looking for the biggest, most vibrant city on the Bay, you can’t miss Baltimore’s Inner Harbor. Tucked up the Patapsco River, you’ll find this city’s waterfront to be one of the most diverse and exciting around. Several major marinas are ready to host you right in the middle of the action. Major attractions include the National Aquarium, the Maryland Science Museum, and the historic Fells Point area of the city.
Nestled up the Chester River on the Eastern Shore, Chestertown may be the complete opposite of Baltimore. This is an old, quiet town. The revitalized downtown area is within walking distance from the marina. Strolling the beautiful streets, you’ll find a weekly farmer’s market and numerous cafes, fine dining establishments, and knick-knack shops. The city marina has updated floating docks. You can also anchor in the river, but protection is limited if the wind pipes up.
Rock Hall has etched out its reputation as a sailing destination. This little town on the north side of the Bay Bridge nearly has more marinas than it has residents. You’ll find quaint shops, seafood restaurants, and any marine service you require.

Central Bay

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Annapolis is the capital of Maryland and the sailing center of the Bay. The gorgeous downtown stretches uphill from the city marina and docks, ending in the stately capitol building. The streets are busy with activity, and shopping and dining are never far from hand. Don’t miss a tour of the US Naval Academy.
Once off the Bay and the Severn River, moorings line the inner harbor along Spa Creek. Across Spa Creek, the neighboring Eastport offers many more dining choices. A little quieter than Annapolis, Eastport is worth walking around too.
If you’d rather stay outside of town and tour via land, don’t miss the Herrington Harbor marinas. Herrington Harbour North and South are located near the town of Deale on Maryland’s western shore. These are mega marinas, full of sailors, both resident and transient.
Across the Bay, on the Miles River, lies the city of St. Michaels. If there is one Chesapeake Bay port that you can’t miss, it’s St. Michaels. The main harbor has several marina choices, as well as the Chesapeake Bay Maritime Museum.
St. Michaels is popular with visitors who drive or sail in, and it’s busy on holiday weekends. The streets are lined with shops, cafes, and wonderful restaurants. Don’t miss the winery, local craft brewery, or the distillery. Their Sailor’s Rum is especially tasty.
Back on the western shore, off the Patuxent River, lies the town of Solomons. Lying at approximately the half-way point on the Bay and with an easy harbor entrance, Solomons is a popular layover point for cruisers. Once inside the protection of Back Creek, you’ll find marinas lining both shores. Don’t miss the Calvert Marine Museum, which has many exhibits on the Bay’s natural history in addition to boatbuilding techniques and an original screw-pile lighthouse.

Southern Bay

The last stop on the eastern shore, Cape Charles started as a railroad town. Freight was loaded onto barges here for the trip across the mouth of the Bay. Of course, that was before the Chesapeake Bay Bridge-Tunnel was constructed. Today Cape Charles is a quiet getaway for sailors and land-based visitors alike. You’ll find delicious restaurants, and a local brewery and cidery. The sunsets from the beach at Cape Charles are pretty spectacular, too.
Heading south, the first major cities you’ll arrive at include Yorktown and Hampton. Several marinas serve the area. From here, visiting the nation’s historic triangle, with the towns of Yorktown, Jamestown, and Williamsburg is easy and enjoyable.
After the tranquility of sailing Chesapeake Bay, entering the harbor at Norfolk is a bit of an eye-opening experience. The secure Navy port is lined with aircraft carriers, warships, and support ships of every size and shape. The commercial port is abuzz with activity at all hours. Nevertheless, this is a busy waterway that connects Chesapeake Bay with the Atlantic Intracoastal Waterway ICW. The waterway’s Mile Zero starting point is here, and it then runs south all the way to Key West, Florida.
At this point on the Elizabeth River, the charming town of Portsmouth lies to the west and busy Norfolk to the east. Both have welcoming marinas that allow you to explore, shop, and dine.

Sailing Clubs, Groups, and Events

Numerous clubs and groups call Chesapeake Bay home. When you land in the Bay, be sure to pick up on the local free publications at your marina. Several travel magazines are boater specific. Spinsheet, a local magazine for sailors, is based in Annapolis and features everything you need about sailing Chesapeake Bay. They maintain an active list of sailing clubs and groups on the Bay, as well as current events and happenings every month of the year.
If you’re looking to meet up with other sailors, by no means should you miss the United States Sailboat Show, held in Annapolis every October. This is the largest boat show in the US, and it takes over most of the harbor and mooring field.


Chesapeake Bay is one of America’s cruising gems. There are miles and miles of wonderful exploring and wide open sailing. Wonderful restaurants, with fresh oysters and crabs, are never more than a few hours away. Whether you’re just looking for a new adventure, or a tropical traveler looking for some protection during the next hurricane season, Chesapeake Bay has something for everyone.


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