by Captain Lisa Batchelor Frailey

Immortalized by writers, naturalists and artists, the Chesapeake Bay is America’s ultimate cruising destination.  Explorer Captain John Smith described it as “a faire bay encompassed but for the mouth with fruitful and delightsome land” when he created the first maps of the Chesapeake in 1608. A visit to the Chesapeake includes history, beautiful scenery, wildlife and plenty of action.

Origins and History

The Chesapeake Bay formed over 10,000 years ago when melting glaciers effectively “drowned” the Susquehanna River valley. It is the largest estuary in North America, extending 200 miles from Havre de Grace MD to Virginia Beach VA, and measuring 30 miles across at its widest.  Its 11,600 miles of shoreline exceed that of the entire US West coast – a gunkholer’s dream come true.

Chesapeake Bay is steeped in history, perhaps best captured in James Michener’s epic novel “Chesapeake.” The Chesapeake and most of the rivers feeding it carry names from the original Native American residents. English colonists seeking land and opportunity arrived in the Chesapeake region during the early 1600s.

Many towns along the Chesapeake played crucial roles in the War of Independence, the War of 1812 and the American Civil War. Privateers and pirates (including William Kidd and Edward Teach / Blackbeard) also played a big role in shaping the Bay.

Visitors can step back in time and explore the nation’s history in many museums and historic settlements throughout the Bay. Shoreline villages still host shipwrights, crab shanties, bascule bridges and scenic lighthouses. Classic oyster skipjacks, crab scrapers and oyster tongers ply the Bay as they did a century ago.

Seafood Nirvana

The Bay’s estuarine nature (the combination of tidal waters and freshwater influx) makes seafood fresh and plentiful; over 500 million pounds of seafood are harvested each year.  Savor the best crab dishes ever in the Chesapeake – known as the blue crab capital of the world. Try your hand at “chicken-necking” and catch crabs from your sailboat! Oysters are one of the Bay’s most valuable commercial fisheries, and you’ll find oysters served every way imaginable.  Another favorite is Rockfish – not only excellent sport for recreational and commercial fishermen, but also great eating.

Planning your Sail

You can reach the Chesapeake Bay by plane, train, car or boat.  Baltimore’s airport and rail station are most convenient for the northern reaches, and Norfolk for those starting south. Cruisers enter the Bay through the Chesapeake & Delaware Canal, or from the Atlantic at Cape Henry. The predominance of bareboat charter companies is located in Annapolis, but you’ll find ASA sailing schools and charter bases along the 200 mile length of the Bay. This distribution is ideal, as the Bay’s size and variety allows you to explore on many visits without ever repeating a destination.

Most charter bases operate from mid-April through October. While mid-summer weather is typically hot and humid, you’ll find good sailing winds throughout the season. Early Summer and Fall are favorites, and holiday weekends are in high demand. Prevailing winds are not distinct, but Southerly to Westerly winds are most common in the summer, heavily modified by sea breeze and local topography. Thunderstorms can be wild, so be sure to keep a weather eye and plan accordingly. Tides and currents are easy to manage, since the tidal range for most of the Bay is only about 1.5 feet.

Provisioning is simple; most charter bases have well-stocked grocery stores nearby. Be sure to plan for a few meals ashore to experience the local flavors and specialties.  Fuel, water, ice and pumpout stations are conveniently located throughout the Bay. Sailors can berth in marinas ranging from luxury resort to “mom ‘n pop”, anchorages or moorings in major harbors with water taxis, or secluded anchorages where herons are your closest companions.

Notable Cruising Destinations

The Chesapeake offers remote, unspoiled beauty in close proximity to cosmopolitan city centers. The variety is so diverse that it’s impossible to capture it all in a lifetime of cruising, much less to describe it in a single article. From north to south, here is a sampling of notable destinations to whet your appetite.

* Sail the Patapsco River into Baltimore Inner Harbor, featuring museums, shopping, dining, arts and major league sports in a waterfront urban setting.

* On the Eastern Shore, Rock Hall features the annual “Pirates and Wenches Fantasy Weekend”.

* Annapolis visitors can enjoy a bustling port town, state capital and the home of the US Naval Academy. Known for the National Sailing Hall of Fame and US Sailboat shows, Annapolis features the largest selection of bareboat charter yachts on the Chesapeake.

* “The Town that Fooled the British”, St Michaels is one of the most charming colonial towns on the Bay’s Eastern Shore. Visit the Chesapeake Bay Maritime Museum and wander the brick-paved sidewalks to browse shops and galleries.

* Glide through the bascule bridge at Kent Narrows, lined with workboats and skipjacks. Continue up the Choptank River to find abundant snug anchorages off the meandering tributaries of Broad Creek. Watch soaring osprey dive for fish, and keep your eyes open for celebrity estates!

* From the Choptank, follow the Tred Avon to the beautiful waterfront town of Oxford.  Marinas and restaurants nestle among tree-lined streets; don’t miss the iconic Cutts & Case Shipyard. If Oxford seems familiar, perhaps you’ve seen one of the many films set there.

* At the mouth of the Patuxent River, Solomons offers sailors a host of fine marinas and the world-famous Tiki Bar. Climb the Drum Point Screwpile lighthouse, take a cruise on a Skipjack, or wander through a sculpture garden featuring works from the Smithsonian.

* Enjoy a pile of steamed crabs in Crisfield, the “Crab Capital of the World”. Crisfield’s National Hard Crab Derby features feisty crabs racing on a track, and the largest boat-docking completion on the Chesapeake. Nearby Deal Island hosts the annual Skipjack race.

* Step back in time on Tangier Island, one of two island communities of watermen in the Chesapeake. You’ll hear a relic Elizabethan dialect still intact from the island’s original Cornish settlers. Distinctive crab shanties line the channel to the harbor; bikes and golf carts are the principal transportation ashore.

From cosmopolitan Baltimore to the time capsule of Tangier, the Chesapeake Bay is a cruiser’s dream. Capt John Smith’s words still ring true: “heaven and earth never agreed better to frame a place for man’s habitation.” Or, man’s sailing!