Annapolis
Annapolis has a vibe. Certain cities do. Songs are written about New York City’s vibe. San Francisco too. No songs about Annapolis; it’s not that big, but it is historic, lively and fun.
6 Reasons to Visit Annapolis
Not a History Snooze
Here’s where the vibe comes in. Annapolis is the confluence of history, commerce, political power and boating.

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Annapolis was the commercial powerhouse of the Chesapeake Bay, essentially putting other commercial centers around Bay out of business. That fizzled when ships got too big for Annapolis’ little harbor and started docking in Baltimore.

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While its commercial vigor fizzled a bit, Annapolis is still a political powerhouse. The Continental Congress met in Annapolis to ratify the “Treaty of Paris,” formalizing separation from Great Britain.
More Original 18th Century Buildings Than Any Other U.S. City
Five of the Colonial Georgian mansions in Annapolis are open to the public. Others are still used for homes or have been turned into offices, shops or restaurants.
“Sailing Capital of the World”
Actually, Annapolis competes with Newport, Rhode Island, for the title. Newport has hosted America’s Cup regattas, while Annapolis leads in number of boats compared to the population..
But the Annapolis city council settled the issue by passing a proclamation in 1995. So, there you go Newport.
Historic Higher Learning
Downtown Annapolis is the home of the U.S. Naval Academy and St. John’s College, a 300-year-old liberal arts college unlike no other in the country..
St. John’s was created before colleges had curriculums and it hasn’t changed. Students study the “great books” toward a liberal arts degree.
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The result is a vibrant nightlife. Nearly every bar — and there are a lot of them — have music every weekend. Walking about you’ll find casual hipsters, formally-dressed midshipmen and mid-life boaters in their athletic wear.Shops & Eateries
The historic downtown is full of unique boutiques and restaurants. Internationally renowned Hobo bags started here and still has their original shop downtown.


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While Main Street in historic downtown is home to an unusual number of colonial bars.
The main places to see are City Dock (the waterfront), Main Street (the business/shopping district), State Circle (state capitol area), U.S. Naval Academy, Eastport (historic neighborhood of former watermen homes & boaters’ bars), and West Street (uptown area of bars & restaurants).
Cool Tours Abound
The Visitor’s Center (26 West Street) is a good place to start. It has public restrooms and people standing by to answer questions. You’ll find ghost tours, home tours, food tours and even a scavenger hunt tour. Here’s a list of walking, boating, Segway, cycling, kayaking tours.

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What’s on Main Street?
City Dock/Ego Alley (downtown waterfront)
State Circle (state capitol area)
. West Street (hipster area)
. Maryland Avenue (antique row)
. Eastport (historic waterman-neighborhood)
. Colonial Annapolis
. U.S. Naval Academy
. Haunted Houses & Pubs
. What Else?
. Getting Around
