Cruising the Chesapeake Bay

The Chesapeake Bay has become an increasingly popular destination for cruisers over the past few years with the development of more “main stream” charter companies throughout the area. The bay offers hundreds, if not thousands, of destinations for cruisers, with everything from quiet anchorages to the big city environments of Baltimore and Washington D.C. With hundreds of miles of coastline to explore and the ability to never visit the same place twice, it’s no shock that many leisure sailors have their sights set on the Chesapeake these days.

If you’re thinking of chartering a boat for your bay cruise, I would suggest beginning your trip from Annapolis, Maryland’s capitol city and the “Sailing Capitol of the U.S.” as it has been commonly described. Annapolis offers a wide variety of well established charter companies from Sunsail to the Moorings and others like Lets Go Cruising. The best times for a bay cruise would most likely be in the late spring, late April through early June, or in the early to mid fall, September through October. Planning a trip around this timeline will allow you to avoid the heavy crowds of the summer season and to capitalize on the best weather that the region has to offer. The late spring typically sees the traditional Chesapeake Bay “sea breeze”, a moderate but dependable Southeasterly breeze, while the fall season enjoys brisk Northerly and Northwesterly winds. The last suggestion that I would make would be to select a boat with a relatively shallow draft, as the bay is generally very shallow. The sandy bottom is quite forgiving however, if you make an error in navigation. Don’t forget to bring your sailing gear however, because the weather does have the potential to turn quite chilly during both seasons.

A course due East from Annapolis, will bring you to the Kent Narrows, a very scenic location full of bars and restaurants. The area is very docking friendly with several marinas and mooring fields to choose from. Weekend activity in the Narrows can get quite busy, so plan accordingly. Additionally the area is very tidal with a rather strong current that rips through the narrow channel. Continuing South, around Tilghman Island, following the Choptank River to the Tred Avon River, will bring you to the quaint town of Oxford, on Maryland’s Eastern Shore. While in Oxford, take the time to visit the Tred Avon Yacht Club for dinner or a few drinks. If your visit to Oxford occurs in the fall, you may be able to watch some local Log Canoe racing, a very popular and traditional style of wooden Chesapeake Bay racing sailboats. Oxford is also very cruiser friendly with several marinas and anchorages to make a selection from. The town also offers a wide variety of bars and local restaurants.

Continuing on your Southerly route down the Bay, but on the Western shore, you could make a visit to Solomon’s Island, located on the Patuxent River. Solomon’s Island has become increasingly tourist friendly over the years and boasts a wide variety of seafood restaurants, marinas, and even a board walk along the river. The Calvert Marine Museum is worth a visit and even offers outdoor concerts and harbor cruises during the warmer months. Finding a quiet anchorage in the Patuxent River or a slip at one of Solomon’s Island’s marinas is not a problem, however, if your visit is during a weekend, it may be wise to call ahead to reserve a slip.

For your final destination before turning North, I would recommend visiting historic St. Mary’s City on the shores of the St. Mary’s River, just south of the Patuxent. This was the first colony on the Chesapeake and was Maryland’s capitol city before it was moved to Annapolis in 1695. English settlers arrived here on the Ark and the Dove, a replica of which is open to the public. The first capitol building is also an open attraction and a full replica of colonial life is available to see.