Chesapeake Bay
America’s Great Estuary
REED’s RECOMMENDS: With its thousands of anchorages, small
harbors and an anchor-friendly bottom of good, sticky mud, there
are few places as pleasurable to the cruising sailor with an open-
ended itinerary to explore as is the Chesapeake Bay. With its light
airs and afternoon storms in the summer, there’s ample opportunity
to use all your skills, with an anchorage always nearby.
One of the high-water marks of the sailing calendar is the annual
Great Chesapeake Bay Schooner Race, held every year in early Oc-
tober. The 127 nm race begins at the Chesapeake Bay Bridge at An-
napolis and finishes in Hampton Roads. Whether you volunteer to
crew or simply watch the fleet from your boat, it is a stirring event.
On your way down the bay, the islands of Smith and Tangier (in
the area of 35°N, 75°W) offer a window into a lifestyle nearly van-
ished, that of the watermen, making their living by harvesting the
Chesapeake Bay blue crab and oysters. To enter Smith Island, follow
the “Big Thoroughfare” and respect all buoyage. Call the very afford-
able Smith Island Marina on VHF68 for directions and 410-425-4220
for reservations. With less than 400 residents, Smith Island is a quiet,
pleasant place that has still escaped the attention of most of the rest
of the world.
Just across the state line is the more populated Virginia island of
Tangier. While it is more of a “destination” for tourists than its larger
neighbor, Smith Island, it may be the least touristy vacation island
you’ve ever seen. Somewhat easier to enter, the James Parks Marina,
slightly more expensive than the Smith Island Marina but just as
friendly, can be reached at 767-891-2581 or VHF 16. You won’t be able
to say you have had a proper visit to Tangier Island without lunch or
dinner at Hilda Crockett’s Chesapeake House. Food is served family-
style; make a reservation at 757-891-2331 and show up hungry.
Sailors heading south for the winter should time their cruise with a
layover to visit the US Sailboat Show, held each year over Columbus
Day weekend at the City Docks in the salty town of Annapolis (the
US Powerboat Show is the following weekend). Join the locals for
beers and laughs when the boats leave their slips as the show closes at
6 p.m. sharp on Columbus Day; it’s a raucous sight that must be seen
to be believed.
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