Annapolis weekend scene

Weekend itinerary

An Annapolis weekend itinerary

Arrive for a City Dock walk Friday, pair the Naval Academy and historic core Saturday, then cross to Eastport or sail Spa Creek before Sunday departure.

By Cal Mercer — a Second Star Guide itinerary

Annapolis fits maritime, civic, and neighborhood scenes into a two-night stay: City Dock, the Naval Academy, State Circle, Eastport, and Spa Creek.

Best length

2 nights

Two nights cover downtown, the Naval Academy, State Circle, Eastport, and one water outing without turning the weekend into a Chesapeake driving tour.

Stay

Historic Inns of Annapolis

Three connected historic properties around State Circle put brick streets, the State House, Main Street, and…

Main activity

City Dock, the Naval Academy, State Circle, and Spa Creek

The strongest first weekend combines civic Annapolis, Navy Annapolis, and the sailing city around Spa Creek.

Geography

Historic core and Spa Creek

Keep Friday around City Dock, Saturday between the Naval Academy and State Circle, and Sunday near Eastport or on the water.

Sailboats gathered around Annapolis City Dock
Friday belongs to Ego Alley, City Dock, and the brick streets climbing toward Church Circle.
Waterfront view near the United States Naval Academy in Annapolis
Saturday morning pairs the Naval Academy with the Maryland State House and historic streets.
Marina and boats in Annapolis Eastport
Eastport gives the weekend a working-marina counterpoint to downtown's civic landmarks.

Friday

Park, check in, and meet Annapolis at City Dock.

Walk Ego Alley while the boats return, follow Main Street uphill toward Church Circle, and keep dinner close enough that the car can stay put.

4:00 PM

Saturday

See the Naval Academy, State House, and the brick historic core.

Start with current Academy visitor access, continue through City Dock and State Circle, then save the later afternoon for a cruise, sail, or slower waterfront walk.

4:30 PM

Afternoon

Return to the water in late afternoon.

Take a scheduled sail or cruise when conditions suit, or walk City Dock and the Spa Creek bridge as masts gather against the evening sky.

Sunday

Cross to Eastport or take one last look from the water.

Eat breakfast, walk the Spa Creek bridge, look into the marinas, and leave before Washington-Baltimore traffic compresses the afternoon.