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Chartering Chesapeake Bay

Chesapeake Bay is a body of water than can be both intimate and absolutely enormous all at the same time: a cruising ground where you can enjoy a first-class meal one night and rough it on the hook the next, without ever having to sail more than a few miles.
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Annapolis is a true hub of sailing activity

A big and little body of water—all at the same time

Looks can be deceiving on the Chesapeake. It’s a body of water than can be both intimate and absolutely enormous all at the same time: a cruising ground where you can enjoy a first-class meal one night and rough it on the hook the next, without ever having to sail more than a few miles. It’s the kind of place that will continue to surprise even the saltiest of sailors after a lifetime of exploration.

Integral to any Chesapeake charter is the bay’s deeply crenelated shoreline. Countless bays and creeks provide literally hundreds of anchorages large and small, not to mention the raison d’être for the dozens of shore side communities—also both large and small—that play such an important role in the life of the bay.

Ground zero for chartering and sailing in this part of the world is Annapolis, Maryland, home of the U.S. Naval Academy and a number of different charter companies, boatyards and new-boat sales offices—many of them in the quaint community of Eastport, on the other side of the mooring field in front of “Ego Alley,” the thin strip of water in front of the Annapolis harbormaster’s office.

Annapolis itself makes for an excellent stop and is more than worth the price of either a mooring or the motor in from the anchorage off the Naval Academy. (Or, if you can swing it, a slip at one of the town’s many marinas.) For those who have only experienced the town as part of the annual boat show, Annapolis without crowds is a true gem, replete with historic buildings (including, of course, the Academy itself), quiet cobblestone streets and fine restaurants. Early spring and late fall, when most other cruisers have turned their attention elsewhere, can be an especially magical time.

Beyond Annapolis, there are any number of destinations within striking distance, ranging from urban hubs like Baltimore to untold nameless creeks. Directly to the east lies Kent Island, and to the east of that lie Eastern Bay and the town of St. Michaels—a community so steeped in tradition it has to be seen to be believed. Granted, at the height of the tourist season, getting a slip or a table at one of the community’s fine restaurants can be a challenge. But there’s no beating the place for energy, and like Annapolis, in the off-season, the timeless quiet can be nothing less than surreal. Other great destinations along Maryland’s Eastern Shore include Oxford and Cambridge—pleasant towns that boast marinas dotted with characteristic Bay-area boats, Main Streets lined with great shops and friendly people, and restaurants with mouth-watering local blue crabs, clams and oysters.

Meanwhile, directly south of Annapolis lies the historic Thomas Point screw-pile lighthouse, which originally dates back to 1825 and marks the shoal guarding the approaches to the South and Rhode Rivers, both of which offer a number of nooks and crannies where you can drop the hook for the night. Never mind the occasional powerboat that will drop by for a couple of hours and possibly play its music a bit too loud. They always seem to leave as the sun goes down, leaving the sailors with the wooded shore and twinkling lights of the beach houses to themselves.

Beyond that, explore! If a particular sliver of blue toward the edge of the chart strikes your fancy, give it a look. Just be sure to take some care as you do so. While the main channels in the Chesapeake are well marked—in large part to facilitate the passage of the bay’s not insubstantial commercial traffic—things can get a bit dicey along the periphery, where dredging is nonexistent and the mud and silt have a way of piling up. I’ll never forget the time a couple of buddies and I bumped along the bottom for what felt like a half-dozen boat lengths while reaching out of what we’d thought was a nice deep creek off Eastern Bay. Alas, the water in this part of the world is utterly opaque, so you’re inevitably gunkholing by braille. But hey, ain’t that what life and chartering are supposed to be, an adventure?

Read about more charters in the United States:New EnglandSan FranciscoGrand Traverse Bay, San Juan

For highlights, advice and charter company links go to:Five Charter Destinations in the United States

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