Quirky Cruise
December 17, 2020

The Chesapeake Bay — A Small-Ship Cruising Guide

The Chesapeake Bay

By Theodore W. Scull

In the eastern United States, the Chesapeake Bay, fringed by the states of Maryland and Virginia, forms the country’s largest estuary measuring 200 north-south miles. Its present brackish expanse, only about 3000 years old, combines salty seawater flowing northward from the Atlantic and fresh water rivers emptying in from all compass directions.

Chesapeake Bay

Hooper Strait screw-pile Lighthouse at the maritime museum, St. Michaels. * Photo: Ted Scull

The result produced a highly important ecological system and the location for some of the very earliest English North American settlements at the start of the 17th century. Later events did not turn out so well.

The British fought and lost two major wars in these waters — the War for American Independence and the War of 1812. Historical evidence of pioneering habitation can be seen today at Jamestown and forts and battle scars at Baltimore and Yorktown.


Abundant wildlife and undersea creatures place the Chesapeake in the forefront of natural attractions. Situated on the Atlantic Flyway, tens of thousands of ducks and geese stopover and some even winter in these waters. Meanwhile, beneath the surface lurks the succulent Chesapeake Bay blue crab and the soft-shell steamer clam.

Sadly, once abundant oysters have greatly decreased in numbers.

The shellfish industry produced highly specific types of work boats such as Chesapeake Bay bugeyes and skipjacks manned by clam diggers and dredge boats for catching crabs. Unusual six-sided screw-pile lighthouses (built on pilings literally screwed into the bedrock) protected the watermen from running aground on rocks and shoals. A few still exist exercising their warnings and on view at museums.

The attractive ports cities of Baltimore and Norfolk, the Maryland state capital and Naval Academy at Annapolis, and lovely Eastern Shore villages at Oxford and St. Michaels make for delightful cruising destinations.

Chesapeake Bay

An American Cruise Lines’ vessel at Baltimore’s Inner Harbor. * Photo: Ted Scull


Large blue water cruise liners and container ships use Baltimore and Norfolk as embarkation ports, but they put directly to the open sea because the Chesapeake outside the main shipping channels is too shallow to navigate.

Inland water cruising is the bailiwick of U.S. flag coastal ships.

Chesapeake Bay

A large Maersk container vessel loading at Baltimore’s container port. * Photo: Ted Scull

These small ships offer two types of cruises — one-week circuits, usually embarking and disembarking in Baltimore and, occasionally passing-through itineraries. The latter may begin in New York or Philadelphia to enter the Chesapeake via the Chesapeake and Delaware Canal, and after visiting several ports, exit in the south via the Chesapeake and Albemarle Canal, part of the Intracoastal Waterway leading onto the Carolinas, Georgia and Florida.

American-crewed, these small cruisers draw mostly North American passengers who have an interest in seeing their own country and travelling without the hassle of driving and or one and two-night stands on a coach tour.

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The library lounge aboard an American Cruise Lines’ vessel. * Photo: Ted Scull

The food runs from very good to excellent regional American fare using fresh ingredients served at one open sitting, and cabins, nearly all outside and of medium-size. Most open to a side promenade or a small private balcony.

Anticipate a genteel, social atmosphere and informal talks by local historians, in lieu of nightly theatre-style entertainment. The ships usually tie up for the night at a town landing allowing for evening strolls then sail in the wee hours to arrive at the next port after breakfast.


Our family and two others owned a farm on the Eastern Shore for many years, and we spent a lot time at Bennett Point, near Queenstown, when I was growing up. It was here where I first learned about slavery, as our property once had a deep-water landing, referred to as Shipman’s Hole, that allowed slave-carrying ships to nose right up to the shore.

Chesapeake Bay Cruise

I learned how to drive with this WWII surplus Army Command Car and  obviously not where not to drive. * Photo: Helen Sohngen Scull

My best memories are crabbing, clamming and fishing, learning to drive and how to operate a boat with an outboard motor and one with sails, and watching thousands of ducks and geese gather just off shore on their way north or south. The geese had to be watched carefully as should several hundred or more land on the winter wheat field, they could devour the crop in about 20 minutes.

Chesapeake Bay Cruise

Mother slurping an oyster and me looking in amazement. *Photo: Theodore C. Scull

Since selling the farm, I have been back to cruise this glorious bay four times as well as visiting by car over long weekends.

No inland water region is larger or has such intriguing diversity as the Chesapeake Bay.

The itinerary here follows roughly two that I have made by American Cruise Lines and Exploration Cruise Lines, the latter no longer in business.

RELATED: Ted Chats with Captain George Coughlin about Small-Ship Cruising from the 1970s Onward.


Baltimore’s busy Inner Harbor provides a most exciting embarkation in the spring and autumn. Anchored by Harborplace’s large festival restaurant and shopping market pavilions, additional attractions include the National Aquarium, the U.S.S. Constellation, the last all-sail ship designed for the U. S. Navy; Maryland Science Center; major league baseball stadium at Camden Yards; and the B&O Railroad Museum centered around the country’s first railway station.

Great views of the Inner Harbor, sailing ships, excursion boats and water taxi traffic can be enjoyed free from nearby Federal Hill and for a fee from 27th floor of the World Trade Center.

Chesapeake Bay

An historic view from Baltimore’s WTC soon after it was opened as a viewing platform. * Photo: Ted Scull

The coastal cruises usually tie up adjacent to the National Aquarium with ample touring options before or after the cruise, including Washington, D.C., the nation’s capital, just three-quarters of an hour away by train.


At the start of the cruise, the ship slowly threads past Fell’s Point, a lively 19th-century waterfront community; Fort McHenry, which during the British bombardment in 1814 inspired Francis Scott Key to write the American national anthem, Star Spangled Banner; working container ships, tankers, coal carriers, cable layers, hospital vessels, military sealift command ships; and both active and shut down smokestack industries.

The ship then turns south to pass under the soaring twin spans of the Chesapeake Bay Bridge, providing the only fixed link between Maryland’s Western and Eastern Shores. The rotation of port calls will vary from cruise to cruise, but most itineraries visit them counter clockwise.

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Sailing beneath the Chesapeake Bay’ Bridges’ twin spans. * Photo: Ted Scull


Annapolis is home to the U.S. Naval Academy (founded in 1845) and the Maryland state capital with the oldest legislative house in continuous use, dating from 1772-1779. The uphill walk from the landing passes through the attractive city center, while the Naval Academy gates are a couple of blocks along the waterfront. A guided tour reveals impressive French-influenced architecture, the world’s largest dormitory (housing 4,000 midshipmen), and fascinating military traditions. 

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The Superintendent’s house at the US Naval Academy, Annapolis, MD. * Photo: Ted Scull


Then near the bottom end of the Chesapeake, the York and James rivers lead to Yorktown, Jamestown and Colonial Williamsburg.

Following defeat of the Spanish Armada, a permanent English settlement was established at Jamestown in 1607, the first in America, predating Plymouth in Massachusetts by 13 years. The initial exports – crops, salted fish and forest products – were not very successful, but when a shipload of tobacco made its way to England, the settlers, shippers and manufacturers had an overnight success. Tobacco plantations quickly developed and regular transatlantic trade blossomed, and the labor-intensive crop drew the first group of African slaves in 1619.

The region prospered and Williamsburg was founded. Now the world’s largest living museum, Colonial Williamsburg, made up of 500 restored and reconstructed public buildings, houses, workshops, and taverns, reveals 18th century life in what was once the wealthiest and most populous outpost in the British Empire.

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Williamsburg, Virginia and William & Mary College. * Photo Ted Scull

Nearby Yorktown, a once prosperous tobacco port and now a peaceful village surrounded by battlefields, became the definitive stand of the War for American Independence when George Washington defeated Lord Cornwallis in October 1781 directly leading the thirteen colonies to organize into the United States of America.


Crossing the vast waters of Hampton Roads leads to Newport News, Portsmouth and Norfolk with most ships tying up at Waterside, a festival waterfront market adjacent to downtown Norfolk. Within walking distance are the World War II battleship USS Wisconsin, Tugboat Museum, the memorial dedicated to General Douglas MacArthur and the Chrysler Museum’s fine collection of decorative arts and glass and American and European paintings.

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Battleship USS WISCONSIN at Norfolk, VA. * Photo: Ted Scull

From Waterside, the Elizabeth River Ferry crosses to Portsmouth for a stroll through an outstanding historic residential district, featuring mostly 19th-century wood, brick and stone domestic architecture executed in Colonial, Federal, Greek Revival, Georgian and Victorian styles. 

Chesapeake Bay

This waterfront sculpture is entitled The Tourists. * Photo: Ted Scull


Often referred to as the “Land of Pleasant Living,” the fertile soil provides farming as a serious commercial enterprise, gentlemen farmers, an industry that prospers on some of the best seafood anywhere, and an attractive region for retirement. My aunt retired to a Miles River waterfront property near Easton, and I visited her nearly every year over Presidents’ Weekend.

Chesapeake Bay

Opening oysters is not difficult – once you learn the ropes. * Photo: Ted Scull

For many visitors, the famed Eastern Shore holds the most interest with charming towns tucked up tidal rivers that prospered and grew with the lucrative shellfish and farming industries.

At the small town of Crisfield, crab pickers still hand pick the succulent big lump backfin blue crab meat for canning and shipping worldwide. In the late spring, the crab sloughs its shell and before it hardens, eating a whole one in this soft state is considered a great delicacy. Sautéing a pair is my favorite springtime meal.

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Fishing and shell fishing boats on the Eastern Shore of Maryland. * Photo: Ted Scull

From the town pier, a local passenger, mail and cargo boat heads out to Tangier Island, a tiny community of 800 that made its living, and some still do, by crabbing, clamming and oystering. Until recently, some of the oldest residents had Elizabethan tones in their accent, the result of three nearly four hundred years of relative isolation.


Cambridge, located up the Choptank River, is the Dorchester County seat with several streets of fine houses built by rich politicians and captains of industry. But the primary excuse to call here is to access the Blackwater National Wildlife Refuge, home to duck species by the score, Canada and snow geese, bald eagles (US national symbol), golden eagles and osprey (a large fish hawk).


Then at tiny Oxford, facing the Tred Avon, the ship docks alongside the Oxford-Bellevue Ferry landing and dating to 1683, the privately-owned operation qualifies as the oldest of its kind in North America.

Chesapeake Bay

Robert Morris Inn at Oxford, Maryland. * Photo: Ted Scull

Just up the ramp, the Robert Morris Inn, with 18th-century origins, is a notable draw for its restaurant and tavern, and the namesake owner was a major financier of the War for American Independence. My wife and I had a delightful birthday celebration stay there a number of years ago.

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The Oxford ferry to Bellevue is about to cross the Tred Avon River. * Photo: Ted Scull

A peaceful walk through the village of 700 mostly prosperous fisherfolk and retired and weekend residents reveals a great variety of residential architecture, a tiny commercial center of three stores and a major yacht building and repair yard.


St. Michaels, often referred to as the town that fooled the British, is usually the final call on the cruise. As a shipbuilding center, St. Michaels-built warships captured or sank 500 British merchant ships during two wars, prompting a retaliatory attack in August 1813. In anticipation, the citizens darkened the town and hung lanterns to one side high in the trees, to draw away the British guns. The ruse worked and the town was spared, and today the town is a popular weekend destination, and Talbot Street prospers as a small store shopping Mecca.

Chesapeake Bay

A handsome Victorian house at St. Michaels. * Photo: Ted Scull

Back in the days of our farm stays, the only reason we ventured to St. Michaels was to refill the fuel tanks for the outboard motors. It was about a 20-minute run by water and 45 minutes by road.


The cruise ships tie up at the Chesapeake Bay Maritime Museum and its exhibits tell the watermen’s story with two dozen types of workboats, exhibits about duck hunting and the related wooden duck decoy craft, and memorabilia recalling the steamboat era, once the bay’s primary means of transportation before sealed roads and bridges.

The museum’s centerpiece is the 1879-built Hooper Strait Lighthouse, a handsome hexagonal wooden tower cottage built on stilts. A visit inside shows the isolated life of the keeper and his family who once lived well out in the bay.

Chesapeake Bay

Clams and Oysters awaiting eager customers on the Eastern Shore. * Photo: Ted Scull


The Chesapeake Bay is rich in British American history dating from the earliest days of white settlement, then through two major wars, and the period of British aid to the South during the War Between the States. Ecologically, it is one of American richest breeding grounds for shore birds and shellfish, and in the last three decades, the waters have become increasingly popular for well-heeled retirees who come to reside adjacent to working farms.

The Chesapeake Bay Foundation plays a major hand in looking after the region through Education, Advocacy, Litigation and Restoration.

American Cruise Lines is currently the sole operator of Chesapeake Bay itineraries. Three members of its fleet share the 8-day/7-night cruises that operate from Baltimore in May and October and November.


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Posted In:

All Feature Articles, American and Canadian Waterways, Coastal America, Coastal Feature Articles, North America

1 Comment

  1. Anne Kalosh - 2 weeks ago

    Very informative and interesting! It makes me want to explore my own backyard (I’m a D.C. resident) much more thoroughly. Thanks, Ted, for the great color, history and personal notes that always make your stories stand out!

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