Best Places to Retire by the Bay

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

Wednesday Night Races on the Chesapeake Bay near Annapolis. (Photo: Visit Annapolis)

Annapolis, Md.

Population 39,000


Pop. 39,000

Fall in Annapolis

Maryland’s colonial-era capital busies itself in the shadow of the oldest state house in continuous use, thrums with the rumble of speedboats showing off in Ego Alley, and features streets full of uniformed Navy midshipmen most of the year. There’s lots to see and do in the historic Anne Arundel County seat, so retirees looking for a host of cultural and recreational options should consider the “Sailing Capital of the World.” It’s also the largest town on our list, and because of its size, there are options to consider within this option. The Annapolis suburb of Parole, for example, is Niche’s #4 place to retire in the state. Annapolis draws high marks on the AARP Index, particularly for healthcare (63) and civic engagement (62), but its subpar housing score (49) is a reflection that this can be an expensive place to buy or rent.

AARP Livability: 58

Niche rating: A overall

Less costly Shore alternative—Salisbury, Md. (pop. 33,000) has historic neighborhoods, a walkable downtown with college-town flair, and the Shore’s largest hospital—all with housing costing a third or more less than its western shore counterpart. These are just some of the reasons why U.S. News & World Report has the Wicomico County seat on its “Best Places to Retire” list.