The City Dock in Annapolis' harbor is known to locals as Ego Alley. This is where the captains come to show off their boats and people throw bread to feed the ducks. There are plenty of coffee shops to grab a cup of joe and take a seat and watch people stroll by. This is the prime people watching spot of Annapolis. The entire City Dock area is an impossibly quaint place to spend a few hours exploring: walk on the narrow cobblestone side streets, browse the local shops, and check out the adorable row houses.
With its sleek design and glass patio (one of the coolest rooftops in Annapolis), Metropolitan adds a modern touch to the historic area.
A nanobrewery and restaurant in Eastport, right outside downtown Annapolis. Lovely outdoor patio for tasting beers and spying on dogs.
Historic Irish pub located steps from State Circle. $6 Guinness pours and hearty grub.
Long-standing neighborhood pub by the water. Try their famous crab cake pretzels!
If you are looking to enjoy some of Maryland's famous crabs, look no further than Cantler's. An Annapolis, Maryland icon, Cantler’s waterfront crab house has been serving the area’s freshest seafood to watermen, boaters, and land lovers alike for nearly four decades.