Vacation on Chesapeake Bay for Singles 50 and Over

chesapeake-bay-mapSummer is here and our thoughts turn to vacation. A great place to vacation for singles 50 and over (or for anyone for that matter) is the Chesapeake Bay region. If you like water-oriented recreation, fresh air, great seafood, beautiful vistas, boating, fishing, bay cruises, quaint historic towns and sunsets over water, then the Chesapeake Bay is for you! And if you’re from the Northeast or Mid-Atlantic regions of the U.S. the Chesapeake is particularly convenient. If you’re from elsewhere, fly to Washington D.C., Baltimore or Philly and the Chesapeake Bay is at your door step or a short drive away.

Particular points of interest are Baltimore and the Inner Harbor, Annapolis and the Naval Academy, Maryland’s Eastern Shore, the West Shore of the Chesapeake south of Annapolis, and Virginia’s Chesapeake shoreline. But also, the bay itself offers great fishing, boating, ecological tours and beautiful vistas.

First a few words about the bay. Chesapeake Bay is an estuary, the largest in North America, second largest in world. (The largest estuary in the world is the Rio de la Plata, between Buenos Aires and Colonia, Uruguay.) An estuary is a partly enclosed coastal body of brackish water with one or more rivers or streams flowing into it, and with a free connection to the open sea. The Chesapeake Bay is approximately 200 miles (300 km) long from its northern headwaters in the Susquehanna River to its outlet in the Atlantic Ocean. Total shoreline including tidal areas is 3,190 miles according to the National Oceanic and Atmosphereic Administration (NOAA), representing a surface area of 4,479 square miles, (whereas California’s coastline is 3,427 miles). The bay is spanned twice, in Maryland by the Chesapeake Bay Bridge from Sandy Point (near Annapolis) to Kent Island, and in Virginia by the Chesapeake Bay Bridge-Tunnel connecting Virginia Beach to Cape Charles.

An excellent way to get an overall sense of what the bay has to offer is through the travel site “Trip Advisor”. Also the Maryland-based page at is a useful information source. Another excellent source of information is Fodor’s “Virginia and Maryland”. You will need to dig through the various sections of this book to extract information on Chesapeake Bay attractions since there is no one section devoted to the bay. A word of caution, when you go protect yourself against those pesty mosquitoes by using plenty of bug repellent and you should not have a problem.

baltimore-harborBaltimore, Maryland is the largest city on the bay and an interesting city in its own right. In recent decades the city went through a major revitalization program in which older industrial buildings and sites were converted to stadiums and shopping malls. The city’s famous Inner Harbor, now a thriving recreational and residential venue, was once an old and deteriorating industrial harbor. The Inner Harbor is a great place to start your tour of the bay and its recreational offerings. Visit Baltimore Harbor Attractions for more information. The Inner Harbor features excellent hotels, restaurants – especially if you love of seafood and Maryland soft shell crab – museums and historic neighborhoods near downtown. Water taxis are a great and inexpensive way to see the harbor and to travel from one destination to another.

annapolisNext on the bay is Annapolis, Maryland, the state’s capital and home of the United States Naval Academy. Annapolis is considered the sailing capital of the Mid-Atlantic and one can rent cruises of the bay for the day or charter sail boats for longer periods. Annapolis is 350 years young. It is a vibrant city, proud of its charming colonial heritage, and offers visitors the finest in dining, accommodations, shopping and entertainment. The city has numerous excellent bed-and-breakfast establishments as well as major hotels. See Visit Annapolis for more information on where to stay, dine and visit.

Not far south of Annapolis along the western shore of the bay is the town of Chesapeake Beach. Their website is here. Chesapeake Beach offers “quiet secluded beaches, waterfront restaurants, succulent seafood, water park activities and events, and quaint, historic, hometown quality of life” The waterfront park can provide a fun attraction for the grandkids, but it can also mean families with children will frequent the local hotels, if that is an issue. Although it can also mean the kids go to the water park instead of jumping in the pool yelling “Marco Polo!” Check out Chesapeake Beach Resort and Spa.

Across the bay on Maryland’s Eastern Shore lies the attractive town of St. Michaels, which was once a shipbuilding center (two websites of interest are or St. Michaels is one of the region’s premier leisure time destinations. Its narrow streets are lined with cafes, shops, boutiques, waterfront restaurants and art galleries. See the Chesapeake Bay Maritime Museum. The Museum offers exhibits, demonstrations, boat rides on the Miles River, and annual festivals that celebrate Chesapeake Bay culture, boats, seafood, and history. For excellent waterfront accommodations look into The Inn at Perry Cabin and the Victorianna Inn on the St. Michael’s harbor, an attractive bed and breakfast inn.

st-michaels-harborBack on the western shore of the Chesapeake and to the south lies the Virginia coast of the bay, easily as picturesque but less populated until you reach Virginia City where the bay and the Atlantic join. See this site for more. If you’re a history buff you can visit George Washington’s birthplace and the estate of Confederate General Robert E. Lee, Westmoreland State Park with its beach, Caledon Natural Area with its trails to the Potomac River, and charter boats, which show off the charm of this region. But if you want a relaxing resort on the bay check out The Tides Inn in Irvington, VA. They describe themselves as “Nestled on a private peninsula overlooking Carter Creek with a view all the way to the Chesapeake Bay”.

Finally, the Chesapeake Bay offers unparalleled opportunities to learn about the ecology of the bay. See its ecology at work by touring it and learning about the bay at Discover Chesapeake Bay, Chesapeake Bay Ecology Center, and Chesapeake Bay, or the Institute of Marine and Environmental Technology at Baltimore’s Inner Harbor. Also sign up for any of the many chartered tours of the bay.

Have a great trip and tell us about your experiences!
Bob Rodino

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