The Chesapeake Bay: a sailors’ heaven

author: Chiara Filippi

Cover: Annapolis Sailing Boat Show (credits

If you travel east from Washington DC, at less than an hour drive, you find yourself in Annapolis, the capital of the State of Maryland. Annapolis, so called after princess Anne of Denmark and Norway, future queen of England became in 1694 capital of the royal colony and during the 18th century flourished both economically and politically.

The town became the capital of the United States of America for a very short period at the end of the 18th century, and it was in Annapolis that John Shaw designed the first stars and stripes version of the American flag.

Today Annapolis remains a very important historic centre and it well symbolizes the British colonial heritage of the first 13 States. And it is also here that in 1845 the US Naval Academy was founded.

Annapolis and the Naval Academy from the Bay
Sailing boats in Oxford’s marina

Annapolis owes its fortune to the Chesapeake Bay and from this strategic position the town developed and grew over the centuries. The Bay that extends from Maryland to Virgina, it is 320 km long and more than 150 between rivers and streams flow into it.

It is, in fact, the largest estuary in the United States. It is home to a large number of animals and plants and it definitely is a paradise for nature lovers and water sports’ fans. Fishing for crabs and catching oysters are two of the main economic resources of the area.

Nothing better than dock the boat and enjoy the traditional Maryland’s steamed blue crabs

The Chesapeake Bay on the East coast, together with the San Francisco Bay on the West Coast, is also known to be one of the favorite spots for sailing enthusiasts. Thanks to its natural shape, the Bay allows sailors to cruise protected from the extreme weather conditions of the Atlantic Ocean, but its 48km are wide enough to let them enjoy the winds on long rides on the bay’s waters.

Many rivers end in the bay and provide idyllic views and peaceful and recluse creeks where to drop the anchor and escape the frenzy of everyday’s life.

There are many marinas and ports to dock your boat to

On the shores of the Bay you will find fishermen’s villages and pretty little towns such as St. Michael, Oxford, Deale and Rock Hall, all of them reachable by boat. There are many marinas and small ports where to dock the boat, to enjoy a stroll and visit these well-preserved historic towns.

Visitors can also indulge in the famous Maryland crab cakes and steamed blue crabs in one of the many restaurants. These restaurants can even be reached by boat as many of them have their own piers.

Sunset on Pirates Cove
Strolling or biking is another way to visit the pretty villages of the bay

There are several sailing schools, yacht clubs and charter companies operating on the Bay that rent all kind of boats: from small Lasers or Optimists for 1 or 2 people to big sailing boats and multihulls for larger groups.

Every year Annapolis hosts six Boat Shows two of which, one in April and another one in October, are entirely dedicated to sailing boats. More than hundred boats are docked in front of the city centre and there are numerous exhibitor stands to visit.

Sailing on the Choptank river

Every year, between April and November the small towns and villages organize various events and festival that are worth visiting. Among the many, we would like to o mention the Seafood festival of Tilghman, the Antique and Classic Boat Festival of St. Michaels, the Governor’s Cup Yacht Race from Annapolis to St. Mary’s City and the notorious Oyster Festival of Urbanna.

A typical Inn in a village (about 1876)

The Chesapeake Bay is undoubtedly a must for any American sailors and it is an ideal place both for American history and to discover nature. Exploring the Bay by boat it is also a different and original way to see a different side of American culture and traditions, by delving into its sailing world which is so similar, and yet so different, from the Mediterranean and the European one.

Anchored in the Tred Avon river

Originally published at on May 19, 2016.

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