The Best Places to Sail on the Bay
With its reach extending from Virginia in the south to Maryland in the north, the Chesapeake Bay is the largest estuary in the United States. Its interior coastline of 11,600 miles provides more sightseeing opportunities than the rest of America’s coastline combined. A year-round draw for tourists and vacationers, the bay offers a particularly enchanting allure during the fall with the changing colors of the autumn leaves and the crisp freshness of the seaborne air. Such qualities, coupled with off-season hospitality prices, lend the bay a certain measure of popularity – particularly among sailing and other ocean-going enthusiasts. The bay accommodates with numerous available destinations, ranging from the popular and suburban to the positively isolated.
One could easily spend months exploring any given portion of the Chesapeake and its tributaries, and still leave various sights and experiences un-sampled. What follows is a compilation of a few noteworthy travel destinations, popular among sailing enthusiasts and “landlubbers” alike… but perhaps uniquely enjoyable from the perspective of a waterways approach.
Solomons Island is a smooth 49 nautical miles (nm) from Port Annapolis. It lies just within the mouth of the Patuxent, along the western side of the bay, which leads in turn to a variety of other pleasant destinations. Further up the Patuxent, about 8 nm in, one comes to Broomes Island. Broomes is a small, pleasantly rural community, known to many for the mouth-watering fare available at Stoney’s Seafood House – a popular destination for over 20 years.
The Pearl of the Chesapeake, Rock Hall is a waterfront town located directly on the bay’s eastern shoreline, 19 nm from Port Annapolis. The local Fall Festival is not to be missed, and rural Rock Hall offers a variety of annual festivals and celebrations deeply rooted in long-standing tradition – among them, the “Pirates and Wenches Fantasy Weekend” festival in August. The town also offers a wide variety of restaurants, marinas and marine-related activities, kayak and sailboat rentals, wildlife refuges, and rustic bed-and-breakfasts.
The Chesapeake Bay’s largest island, Kent Island is located almost directly across the bay from Annapolis. The town’s modest suburban population is quite proud of their heritage – boasting locations and individuals of note going back to the late 18th century. Among the many surviving historical locations are the Cray House, the old Stevensville Post Office, and the Stevensville Train Depot; some of these locations offer rare insights into early post and plank construction methods. The island additionally offers a wide variety of scenic hiking trails, and the usual array of suburban shopping and fine dining experiences.
Baltimore is a leisurely 29 nm from Port Annapolis. Along the way, you can enjoy some of the most scenic landscapes that the northwestern portions of the Chesapeake have to offer. Baltimore offers a rich local culture, and the full range of amenities of modern city life. It’s also a city with a rich historical tradition, going back to the days of America’s founding and prior colonial life. Fort McHenry, birthplace of the national anthem of the United States, sits in the mouth of the Baltimore Harbor. It’s an excellent addition to anybody’s itinerary for a weekend excursion.
If you’re up for a longer cruise along the Chesapeake’s calm waters, you’ll find Chesapeake City, 52 nm northeast of Port Annapolis. Chesapeake City is actually split in half by the C&D Canal, which was built in 1839. The town hosts numerous old homes from that era of US history, which exist today as quaint, thoroughly enjoyable bed & breakfasts. There is a local historical museum, and several places on the national register of historic places – including the canal’s Old Luck Pump House.
Queenstown lies along the eastern coastline of the Chesapeake, almost directly east of Port Annapolis, and well worth the visit. Queenstown offers beautiful scenery and particularly rich history. Though its present population numbers only a few hundred, Queenstown was once the seat of Queen Anne’s County, and it was a major hub for trade in the 1700s. Several buildings from the town’s early history sit on the historic register, including Bloomingdale, Bowlingly, and the local St. Peter’s Church. If history isn’t your thing, the Queenstown Premium Outlets offers dozens of major name-brand shopping options. There are also several local golf courses of repute, including two 18-hole options with scenic views of the harbor: The Lakes and The River.
The episcopal parish established in Talbot County in 1677 led eventually to the founding of the town of St. Michaels in the mid-18th century, as well as being the direct inspiration for its name. 27 nm from Port Annapolis, the town’s major industries once included shipbuilding and tobacco farming. The town is an early example of urban planning in the New World, and features concepts in urban development that were innovative at the time – such as the presence of a large central square, or “town commons.” St. Michaels’ attractions include the Chesapeake Bay Maritime Museum, well worth the visit, along with several historical civilian and naval vessels.
Sharps Light is a lighthouse set nearly 3 miles south of Tilghman Island, on a concrete foundation set into the bay itself. Its located 22 nm southeast of Port Annapolis, making it a worthy landmark for anyone’s weekend excursion in the Chesapeake’s southeastern quarter. A 1977 ice flow caused the lighthouse to tilt dramatically, evoking an effect similar to that of the Leaning Tower of Pisa. The third lighthouse to be built on that location, the Sharps Island Light – a sparkplug lighthouse dating to 1882 – was deactivated in 2010. Under the guidelines of the National Historic Lighthouse Preservation Act, the location has been up for sale since 2006.
The three-mile-long Rhode River is found 11 nm south and slightly west of Port Annapolis. One of the earliest points of Maryland settlement, having been originally surveyed in the mid-17th century, Rhode River offers seven named tributaries and coves. Each of these is beautifully scenic and very welcoming for short individual trips – or perhaps a weekend-long adventure. Among the river’s attractions is the recently opened Franklin Point State Park, just off of Dent Road (which is available for daytime use, per individual agreement with the Maryland Park Service).
There are dozens, if not hundreds, of other viable destinations lining the nearly twelve thousand miles of coastline along the edges of the Chesapeake Bay; it is almost a certainty that there will always be something new to see and experience. With careful planning, even a day cruise along the Chesapeake Bay can become a series of exciting adventures!