May 10, 2016

The Destination: Annapolis, MD

Why not spend Memorial Day on the water? The historic harbor town of Annapolis boasts great local cuisine, shopping, and recreational activities

Located on the Chesapeake Bay at the mouth of the Severn River, Annapolis is just 25 miles from Baltimore and 30 miles from Washington, D.C. It’s the state capital of Maryland, and it once served as the capital of the United States for a year. Needless to say, the city is steeped in history and culture, and it’s perfect for a Memorial Day Weekend getaway.

When it comes to lodging, travel experts recommend the Historic Inns of Annapolis, a trio of landmark boutique inns in the city’s quaint downtown district (prices are in the $175-$350 range). Alternatively, you could try one of the city’s many charming B&Bs.


Downtown District

The city’s quaint, historic downtown district is a great place to indulge in some retail therapy. The area abounds with quirky boutiques and specialty shops; you’ll find great fashion, antiques, art, and seasonal gifts.  


Annapolis City Dock

Boasting over 533 miles of shoreline, Annapolis is a prime destination for boating enthusiasts. All sorts of eye-catching vessels tie up at the city dock during the warm months, and it’s definitely worth taking a stroll down to the water to take a look.


Schooner Woodwind

Annapolis is “America’s Sailing Capital,” and you’d be remiss if you didn’t set aside some time for a true sailing experience on your trip. Schooner Woodwind Sailing Cruises offers two-hour public sails from the historic Annapolis waterfront into the Chesapeake Bay. You can take a sunset trip, go on the overnight “Boat and Breakfast” sail, or enjoy a wine-tasting cruise. Whichever option you choose, you’ll get a firsthand look at the region’s beautiful coastline.


U.S. Naval Academy

The fabled U.S. Naval Academy is among the city’s most famed attractions, and it’s a must-see for first-time visitors. Book a tour of the grounds to soak up the history of the place and hear stories of famous alumni like Senator John McCain and President Jimmy Carter. If you visit during the school year, be sure to catch the young men in uniform at noon formation in front of Bancroft Hall.


Chesapeake Crabs

You can’t visit Annapolis without getting in on some fresh Maryland Blue Crabs. Jimmy Cantler’s Riverside Inn is an iconic waterfront restaurant that offers a range of delectable seafood: Blue Crabs, crab cakes, clams, oysters, lobster, and scallops, to name a few options. The Boatyard Bar & Grill is another favorite among sailors and boaters, and its famous crab cakes won’t disappoint.

For more information about the best dining, shopping, lodging, and recreational options in Annapolis, check out