Weekend Trip Idea: Annapolis Maryland

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I’m a sucker for a good harbor town and duly impressed by military pomp and circumstance.  Annapolis Maryland has both of these, and since Preakness is this weekend, I’m Maryland-theming the blog.

Annapolis, a town of just under 40,000, is located on the Chesapeake Bay just 26 miles south of Baltimore and 29 miles east of Washington DC, is probably best known as the home of the United States Naval Academy.

If you’ve never been to one of the military academies, they’re impressively kept, and picture-like in their pristineness.  I’ve never been to the Naval Academy but have been to West Point several times.  You could easily spend a couple of hours wandering the grounds, admiring the monuments, and reading the hundreds of plaques and historical markers; the entire campus is something of a living museum.

Downtown Annapolis is bisected by “Ego Alley”, a narrow waterway surrounded by shops, eateries, and bars, where boats come to dock.  Several trip advisor posters warn that it’s full of “rich jerks in fancy boats” wearing ridiculous boaters and pastel shorts”, so if that sort of thing makes your blood boil, maybe avoid Annapolis.  Me? Well, being a rich jerk with a fancy boat is basically my life goal and I spend 75% of the summer dressing like I’m a Kennedy on my way to the cape, so I’d feel right at home.  I could also watch boats come and go for hours.  It’s like a nautical themed tranquilizer.

This is how I pack for Preakness...I BELONG ON A YACHT.
This is how I pack for Preakness…I BELONG ON A YACHT.

If you’re looking for a more active vacation repertoire, Annapolis offers several options.  You can charter a boat for the day.  If you really want to become an old pro at the yacht club, enroll in a weekend long program at the Annapolis sailing school and the historical kayak tours of the harbor get really great reviews online from a multitude of websites.

If I were you (and I realize I’m not), I’d plan my trip around whatever act is at the Ram’s Head Tavern.  It’s a pub and restaurant that doubles as a small time concert act.  I just skimmed through their schedule and they get pretty decent acts.  They recently hosted the Spin Doctors and let me tell you, nothing is better than a 90’s one hit wonder concert.  I speak from experience here.

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