Best Places to Retire by the Bay

Looking to settle down on the Bay? Here are a dozen places to check out.

Looking to settle down on the Bay? Here are a dozen places to check out.

Sittin’ on the dock of the Bay watching the tide roll away … Any number of people who love the Chesapeake dream of making Otis Redding’s words their reality when retirement comes knocking. Could it get much better than relaxing in retired bliss, grabbing a meal at a cute bistro, getting in a leisurely nine holes, or maybe puttering about on your boat?

If you want to retire in Chesapeake Bay country, the decision to make is where, exactly. The region offers a lot to retirees, with urban, suburban, and small-town options for every pocketbook. That means there really isn’t one question to ask yourself but rather several jumbled together. Do you want to get away from it all, or to it all? How will your healthcare needs be met? Will there be fun things to do and other retirees around to do it with? Will you need a car for every errand or is walking an option? And last but not least, what can you afford?

We’ve taken some of the work out of determining where to spend your post-work days on or near the Chesapeake, by turning first to the numbers. Numerous organizations and websites crunch the data on communities to rank or grade them. The AARP Livability Index, for example, examines facts and figures related to an individual community’s housing, neighborhoods, transportation options, environment, health, engagement, and opportunity. While scores technically range from 0-100, anything above 50 is good. (The Index’s highest rated place in the nation—Madison, Wisconsin—only earns 66.) Another cruncher, does a similar analysis, providing overall grades while also scoring places as particularly suited for retirees. We pulled in accolades from a few other sources, and finally added our own intimate knowledge of the region to create a list of retirement bright spots, while providing alternatives for each pick that are either cheaper or geographically different. (The populations are rounded estimates.) If you are looking forward to taking it easy every day, take a look at these options.