Boats sailing in Annapolis, Maryland (Glowimages)

Annapolis and Chesapeake Bay, Maryland (Paul Souders/Photodisc)

Annapolis Maryland Main Street (Hemera)

Boats in Chesapeake Bay Annapolis (iStockphoto)

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What to do in Annapolis

Cradling the past and present, Annapolis is where 20-somethings gather in restored colonial-style bars and where luxury clothing with uppity price tags is hawked behind 18th-century, red-brick storefronts. And no matter where you turn, the state’s most overstated contribution to culinary America, the Maryland Blue Crab, is served. Though quaint and antiquated, the cobblestones are best suited for walking, as car traffic can quickly jam. Walk along the waterfront of the Chesapeake Bay, which locals recognize as the best way in and out of the city. The experience is made all the more authentic by the long-standing presence of the United States Naval Academy. The campus along the Severn River is open for daily tours—an activity that speaks to the time-worn elegance of the city as new-recruit midshipmen march in traditional dress blues.

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