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Annapolis is such a charming town: Just large enough to keep you busy for a few days, while maintaining a human scale. With its quirky street plan (there is a plan), vistas, water everywhere, buildings spanning 350 years of architecture, the capital of Maryland, the seat of Anne Arundel County, and--of course--home to the United States Naval Academy, you'll have lots to keep you interested and busy. Annapolis is literally the city of Ann. It was so named by royal governor Francis Nicholson in 1695. Princess Ann was in line for the British throne so naming the Maryland capital after her was the politically savvy thing to do.
Annapolis doesn't have a parking problem if you know the secret: from Rt 50, take Exit 24A for Rowe Boulevard, cross two bridges, and then just follow signs for Visitors Center parking. The signs will lead you into the Gotts Court parking garage behind the visitors center. It's a six-level garage--you'll come in on the third level (with two levels below you where you'll find the empty parking spaces on a weekday--go down, not up!). This is the best parking deal in town, for a lot of reasons. Everything's an easy, beautiful walk from there. And if walking's a challenge, the city operates the Navy Blue Route which runs every 30 minutes. (But in 30 minutes you can also walk anywhere and back again.) If you take the Navy Blue Route to the Naval Academy main gate or to the dock area, and you want to return to your car in the garage, get off at the top of Main Street, at Church Circle. Walk around the church to your left and down West Street. (If you stay on the city trolley, you'll end up sitting at the stadium parking lot before it comes back downtown again.)
For a nice overview, take the trolley tour from the Visitors Center (26 West Street). Takes about an hour; goes everywhere, sees everything. Air conditioned; cushioned seats (not those slatted wooden seats like on some trolley tours). Additionally you should consider a walking tour of the Annapolis historic district with a colonial guide. This gives you the benefit of stopping in some of the historic houses and the Maryland State House. If you want to tour and eat good food, consider the Annapolis Food & History Tour.
The biggest attraction is the Naval Academy. It's a remarkable institution on a beautiful campus. Just bring a photo I.D. to get in the gate if you're over 21. Allow about half a day: 45 minutes in the Visitors Center to see the free film, visit the exhibits, do a little shopping, enjoy the boats going by in the harbor outside. Then take their 90 minute guided walking tour (recommended), or, if time is tight, get a brochure and tour on your own. The swim center, the chapel, the museum, and the dormitory are all free and open to the public. Tips: Don't miss the chapel--a beautiful architectural space. It closes at 4 o'clock (earlier than everything else on the yard). And Friday afternoons, you might run into a wedding rehersal and they won't let you in; ditto for most Saturdays. But Sundays the services are open to the public: Catholic mass is at 9 a.m.; Protestant service at 11 a.m. In the museum, don't miss the ship models on the ground floor (may not sound exciting, but check it out). You don't have to retrace your steps to the main gate to exit the Academy; you can also walk out Gate 3 onto Maryland Avenue.
Shopping is obvious on Main Street and in the dock area, but Maryland Avenue has nice antiquing and art galleries, design shops and specialty stores; a good coffee shop and a couple of good restaurants. The first block of West Street (where the Visitor Center is located) also has unique art galleries and several good restaurants.
In the dock area, allow some time in the Historic Annapolis Museum at 99 Main Street, a free orientation center with a little bit about everything about the history of the city in a three-story 1790s commercial building: black history, Civil War, the Golden Age, etc. Nice bathrooms, a gift shop, and an elevator, if steps are a challenge.
There are boat rides available in the dock area. You have your choice of motor vessels or sailing vessels; anywhere from 40 minutes to three hours on the water. Check with the Information Booth at the harbormaster's building (public toilets there, too). Nice for when you're tired and want to sit down (the boat rides, that is; though that would apply to the toilets too!).
Annapolis enjoyed a golden age of prosperity and affluence in the decades just before the Revolution. Examine lifestyles of the rich and famous, and their slaves, at the Hammond Harwood House, the William Paca House & Gardens, and the Chase-Lloyd House.
The restaurants downtown are mostly in the dock area and up Main Street. But there are also good selections in the first few blocks of West Street and along Severn Avenue and there's a "restaurant row" across the harbor in the Eastport neighborhood. Everyone has crab cakes and/or rockfish (aka striped bass) on the menu. Steamed crabs are available at Buddy's (inquire about the price; it can fluctuate wildly). But there's also really good Chinese, Italian, sushi, French, Thai, Indian, fusion, et al. Great saloons and fine dining--whatever suits your mood and wallet.
The not-so-obvious but surprisingly interesting attraction downtown is the State House, the capitol building with the black and white dome you see from all over. Open daily, 9-5. Show a photo I.D., and no pocket knives, please. Besides being the oldest state house in continuous legislative use in America, it was also the first peacetime capitol of the United States, when Congress met in Annapolis and officially ended the Revolution by ratifying the Treaty of Paris in what is now the Old Senate Chamber. George Washington resigned his commission to Congress and rode off to Mt. Vernon to be a farmer, deliberately establishing the civilian government's authority over the military--a sublime display of humility, and a pivotal event in Western civilization that stunned all of Europe. The Old Senate Chamber is restored to the exact moment in history when Washington resigned. There are nice exhibits in the State House about Congress' time in Annapolis, as well as exhibits on the construction of the dome (it's a dome-within-a-dome, constructed without any metal), Repousse silver, and Maryland history reflected in legislation like "the Jew Bill."
More on Annapolis is available from Visit Annapolis.
Annapolis sits on a peninsula formed by the Severn River and two creeks. The Severn is one of the "four rivers" in the Four Rivers Heritage Area--which stretches from the Bay Bridge and along the bay to the southern end of Anne Arundel County. In the heritage area, you'll find a concentration of historic sites, waterfront villages and restaurants, tobacco barns and corn fields, and Historic London Town & Gardens.
If you are looking for more information, Visit Annapolis offers a free visitor's guide that will help you find your way!