Browse the Map, but also…
Let’s break it down.
Annapolis has some very distinct areas & neighborhoods. Each is a different adventure.
Main Street is the town center, where the action happens in historic Annapolis. The brick street is lined with former Colonial homes, inns and warehouses that are now lively bars, restaurants, shops and boutiques.
Annapolis Harbor – “Ego Alley”
The Annapolis waterfront area is called “Ego Alley” because boaters traverse into the offshoot to take a lap, turn around at the end and go back out. Boaters enjoy the challenge of the pivot, and check out what’s happening in downtown Annapolis along the way. This is where you’ll find waterfront restaurants, some shops and little parks with great water views.
U.S. Naval Academy
The Naval Academy has regularly scheduled tours. You catch them at the Visitors Center. Check the academy website to see if they’re open to visitors any particular day. A full look-about of the campus can take a day. https://www.usnabsd.com/for-visitors/
Maryland State Capitol
State Circle is the capitol hill of Maryland. The State House (state capitol building) is center of the circle and the governor’s mansion is just outside it. The circle has great views of the city as well as some restaurants and a few shops. https://msa.maryland.gov/msa/mdstatehouse/html/home.html
If you want to stroll through time this is your walk-a-bout. This area has more restored historic homes than any other section of Annapolis. The merchant mansions are on top of the hill. The homes get smaller as you go downhill until you walk past wood-sided watermen houses and Colonial warehouses nearest the waterfront.
Maryland Avenue is the “Antique Row” section of Annapolis, down one of the spokes off State Circle. It’s a little off the beaten path, but a nice stop when touring the historic Colonial neighborhood.
Maritime Republic of Eastport
Eastport is a neighborhood of Annapolis across the Spa Creek bridge, an easy walk from downtown. They call themselves the Maritime Republic of Eastport and make an attempt to secede from the city every year. It turns into a big party. This neighborhood was created by watermen families and has been gentrified by modern boaters, with boaters’ bars, shops, museums and lots of live music during a normal year.
Lower West Street
West Street is the Arts District of Annapolis. But, (lower) West Street is where you’ll find Colonial bars, restaurants and lots of live music on weekends. Several of the bars are said to be haunted. The street is often closed to traffic during the summer for festivals and dining under the stars with tables set up on the street.
Upper West Street
This part of West Street is a “newer” section of town and is known for its hipster restaurants. It’s a bit too far to walk from downtown, but you’ll find trollies, pedicabs or electric carts circling the area to take you around downtown.