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Chesapeake Bay Cruising

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Cruising the Chesapeake Bay, one of the ultimate cruising destinations

America's largest estuary offers more coastline than the country has overall

The Chesapeake Bay, immortalized by so many writers, artists, sailors, and naturalists, is a truly magical destination along the coastal shores of the United States. It is by far the largest estuary with the most coastline of any other Bay within our lands. In fact, its 11,600 miles of shoreline is more than the entire coastline of the US. It drains 64,000 square miles across six states. And although it averages only 21 feet in depth, it has deep channels that run to 100 feet accommodating the passage of submarines and commercial traffic of every description along its 200 mile length. Its width varies from 4 miles at the Bay Bridge to 30 miles at the Potomac . It has more than 150 rivers and streams feeding its rich grounds, and as much variety along its shores as any cruiser would wish to find. So what's not to like? Perhaps the heat, stillness and stifling humidity that characterizes the middle of the summer. But in the Spring and Fall, with the nice long season, it is hard to beat cruising on the Chesapeake.

Thomas Point Light, the quintessential Chesapeake Bay screwpile lighthouse.

From the north, where the mighty Susquehanna flows down from Pennsylvania; to the West, where the port cities of Baltimore, Annapolis, and Washington DC, lie along its tributaries; to the East, where civilization has barely affected the way of life in centuries; there is something for everyone.  And don’t forget Chessie and Chadwick, the Bay’s beloved mascots. 

Whereas the northern and western reaches are relatively highly populated, the eastern shore was isolated until the Bay bringes were built.  Even now, it continues to be more isolated from major metropolitan areas and far more rural than its western counterpart.  Much of the Eastern shore is still farmland that dates to land grants made in the early colonial settlement era.

The entire lower Chesapeake is even more remote, even with the remarkable Chesapeake Bay Bridge-Tunnel spanning the massive expanse at the Bay’s mouth.  What this means is that much of the Chesapeake offers an unspoiled beauty that is hard to imagine in these times and in such great proximity to centers of civilization as cosmopolitan as our nation’s capital.

The Chesapeake Bay has a natural cruising route for discovery.  From the northern approaches, it is possible to enter the Chesapeake from Delaware Bay through the C&D ( Chesapeake and Delaware ) Canal.  This is a traditional route for the “snowbirds” making their way down the ICW to winter the cold weather.  From there, although it is possible to transit the entire length of the Bay from dawn to dusk, the Chesapeake is set up as though made for leisurely hop scotch cruising from shore to shore down its entire length.  Think about the great fun of criss-crossing the Bay with short daily jaunts to charming cruising destinations.

Some Notable Cruising Destinations:

Chesapeake Bay aerial photo (center), showing the DelMarVa peninsula with Delaware Bay on the far side (top right). NASA image taken by MODIS.
  • C&D Canal to Havre de Grace at the mouth of the Susquehanna
  • Havre de Grace to the Sassafras River with its high banks
  • Sassafras to Baltimore's exciting inner harbor on the Patapsco
  • Baltimore to Rock Hall, a fisherman’s town where the food is as fresh as the day’s catch
  • Rock Hall to the Chester River and on to Gray' s Inn Creek, Langford Creek or the Corsica River
  • Chester River through the Kent Island Narrows to the unspoiled gunkholes along the Wye River where the crabbing is unparalled
  • Wye River to St. Michael's one of the most charming colonial towns on the Miles River of the Eastern Shore
  • St Michaels to Annapolis , arguably “the sailing capital of the world” (it is the capital of Maryland and a sailing mecca on par with Newport RI ) and home to the Naval Academy
  • Annapolis to Oxford on the Tred Avon, the quaint, sleepy, picturesque town that was the first port of entry into the colonial states, and on to the mighty Choptank River
  • Oxford to Solomons Island on the Patuxent, where you might run into a cruisers’ gathering and see submarines being tested en route
  • Solomons Island to Crisfield for the Crab Festival, and perhaps on to explore the lovely Nanticoke and Wicomico Rivers
  • Crisfield to Smith and Tangier Islands where you may still hear the lilt of Elizabethan English while crossing into Virginia
  • Smith and Tangier Islands to St Mary ’s City off the Potomac , then on to Washington DC if the adventurous spirit strikes

From here, one could spend another month or two exploring the rivers of the southern bay, all at a leisurely summer pace. But we’ll concentrate on the n orthern b ay for now and leave the southern reaches for dreaming.

We've had the distinct pleasure of sailing the Bay out of Oxford for many years as well as delivering two vessels from the Bay to Long Island Sound. The first time we headed north from Havre de Grace through the C&D Canal and out via the Delaware Bay to a Cape May stopover before continuing offshore around Montauk and into LIS "the long way around". The second time we headed south from Oxford and out the Bay's entrance with a stopover in Sandy Hook before proceeding into LIS via Manhattan and the East River. We'll share a comparison of the two routes as we develop content for this section. We'll also try to provide details for the major destinations on the Bay as we go along, so do stop back often. We welcome your input as well.


There are so many books, guides, and websites dedicated to this great body of water that it's really very difficult and presumptuous to recommend just a few. Nevertheless, those listed below are some of our favorites.

Related Links:

To read some musings about the differences between Long Island Sound and Chesapeake Bay.

Destinations on Chesapeake Bay:

More about Chesapeake Bay


Further reading:

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