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Guide to Annapolis, Maryland

No longer a sleepy town full of boats and midshipmen, Annapolis is now a hot spot for day trips and overnights.

Long known as a world sailing capital, Annapolis is no longer a sleepy town full of boats and midshipmen. Now home to hundreds of new condos, high-class shopping, and three restaurants on the 2007 100 Very Best Restaurants list, this suburb is rapidly becoming a hot spot for Washingtonians to live and play. But, even if you’re not interested in moving, it’s well worth the short drive for a weekend outing.

If you’re headed for a day-long visit of dining, shopping, and overall sightseeing, there are four main areas you must explore:

1. Main Street, the slanted central arm of Annapolis packed with shops and restaurants;

2. Maryland Avenue, the tiny cobblestone path just off State Circle filled with interior design shops, art galleries, and boutiques;

3. The M.R.E. (Maritime Republic of Eastport), just over the drawbridge, a tiny fisherman’s village of charming old homes and restaurants; and of course,

4. The Waterfront, best seen from the docks of Ego Alley or the grounds of the United States Naval Academy.


The Pink Crab (16 Market Space; 410-216-9994). If one didn’t know better, it would be easy to confuse the popped-collar prepsters of Annapolis with their Georgetown counterparts. Regardless of community, this is where they all shop—find the complete line of Lily Pulitzer, Vineyard Vines for ladies, as well as Eliza B. flip flops and other essential prep accoutrements. It’s one-stop shopping that will help you get all “decked” out to go yachting!

Sitting Pretty (35 Maryland Ave.; 410-267-1722). “No clothes are worth dying for. Some, however, are worth living for,” says this store’s slogan. And, it just might be true. You’ll find fancy frocks by names like Tory Burch and Milly, as well as snuggly cashmere sweaters and luxe handbags. Extra friendly sales help makes this boutique a must-stop.

Weekend Living (167 Jennifer Rd.; 410-571-1555). Despite the unlikely location, (a strip center across from the Annapolis Mall) Weekend Living is an underrated gem—stocking everything from cocktail dresses to candelabras. Names like Diane Von Furstenberg, Tadashi, Zelda, and the substantial selection of house wares and jewelry make it worth the extra stop.


Cantler’s Riverside Inn (458 Forest Beach Rd.; 410-757-1311). For over three decades, Jimmy Cantler’s Riverside Inn has served the most famous steamed blue crabs in the region. No matter the weather, hop a boat or make the short drive to this tiny hotspot and order up a bushel (or three) for the table. Plan ahead and make a reservation— come warm weather, Cantler’s is always busy.

Chick & Ruth’s Delly (165 Main St.; 410-269-6737). This Main Street fixture has long been known for two things—their “famous” sandwiches, named for noteworthy locals like Maryland governor Martin O’Malley (roast beef) or Senator Ben Cardin (reuben) and the daily recitation of the Pledge of Allegiance, at 8:30 Monday through Friday; 9:30 on weekends.

Lewnes’ Steakhouse (401 Fourth St.; 410-263-1617). Those yearning for the steakhouses of old will get their fill (literally) at Lewnes’, one of three Annapolis restaurants to net a spot on the 2007 100 Very Best List and the only one to remain on the 2008 list. Find thick juicy cuts of prime beef and generously portioned sides at this local favorite.

McGarvey’s Saloon & Oyster Bar (8 Market Space.; 410-263-5700). Order the “Baker’s Dozen” and learn to shoot like a local—oysters on the half shell, that is. Not quite down with the raw? Try bubbling hot Chesapeake Crab Dip or grab a drink in this red wood building that’s been brimming with drinkers and diners since 1776. It’s the favorite hangout of the Blue Angel pilots.

Tsunami (51 West St.; 410-990-9868). Asian fusion is nothing new, but it isn’t the just food that draws people to city-chic Tsunami; it’s the martinis. This dimly-lit favorite opened in 2004 as part of the West Street expansion and continues to draw a happy hour crowd.


The Blue Angels (Every May). The highlight of Naval Academy commissioning week for many Annapolitans, the annual one-hour show by the Navy’s Blue Angels is always guaranteed to draw a crowd. Watch from the Academy fields or pick a waterfront restaurant and prepare to be amazed—the dips, spins, and up to 700 MPH speed of these five Boeing F/A-18 Hornets are nothing short of awe-inspiring.

The Boat Show (Yacht – June 5-8, 2008; Sailboat – October 9-13, 2008; Power – October 16-19, 2008). The annual boat shows draw thousands each year when this sleepy sailing capital turns into a gigantic floating parking lot for hundreds of new boats. From dinghies to ocean cruisers and boat hooks to sail cloths, this is one event every Washingtonian should attend at least once.

Ram’s Head Tavern (33 West St.; 410-268-4545). This local tavern brings small-town feel (and an on-site brewery) to big name acts. Check the schedule for listings, showing everything from country to comedy to cover bands. Since each show seats less than one hundred, you’re even guaranteed great seats!

William Paca House (186 Prince George St.; 410-267-7619). This historic home might not be Dumbarton Oaks or Hillwood, but the gardens rival some of the best on the east coast. The annual garden sale, held on Mother’s Day weekend, allows visitors to purchase clippings from this famous pleasure garden, which has been in existence since the 1700’s.


Start the day with a latte or scone from City Dock Coffee (18 Market Space; 410-269-0969) or a leisurely Sunday brunch at waterfront Carrol’s Creek (410 Severn Ave., 410-263-8102).

If you want to entertain the kiddies, check out Pirate Adventures on the Chesapeake (410-263-0002)—your very own swashbuckling cruise, complete with pirate garb and face painting. Six cruises daily; $18 per person, $10 under age 3.

If just viewing the water is more your style, walk through the campus of the United States Naval Academy—and if the Gothic architecture and expansive views of the Chesapeake Bay aren’t enough, there’s always plenty of eye candy (the men-in-uniform variety). History buffs might enjoy a guided tour, available through the Armel-Leftwich Visitor Center (click for a tour schedule).

Be sure not to miss out on exploring the town itself. Stroll up Main Street and shop for trendy women’s apparel at several boutiques, or stop in at Zachary’s (100 Main St.; 301-261-2278) for some sparkly gems. Find unique Alpaca sweaters at Alpaca International (206 Main St.; 410-216-9898), and check out local art at Gallery 1683 (151 Main St., 410-280-2140).

Snag to-die-for homemade ice cream (think apple pie or s’mores) at Annapolis Ice Cream Company (196 Main St.; 443-482-3895) and eat it on your way to Maryland Avenue, located just off State Circle and jam-packed with antique stores, art galleries, and trendy boutiques.

Some favorites? In the home department, don’t miss interior design and gift boutique Vie…Necessary Luxuries (86 Maryland Ave., 410-269-6100) or the hearth (and heart) warming tchotchkes at nationally-known artist Natalie Silitch’s (66 Maryland Ave.; 410-263-7177). More of a clothes hound? Score hip men’s wear at Vertu (46 Maryland Ave.; 410-263-3494) or trendy tops at Madison (47 Maryland Ave., 410-295-7878).

Complete the day with a cocktail hour. In nice weather, head to the Pusser’s (80 Compromise St.;  410-626-0004), a Caribbean-themed restaurant on the docks of the waterfront Marriott hotel, for “Painkillers,” their signature drink made with home made rum and enjoy watching the sun set over the Naval Academy, located just across the water.

As you head home, you’ll wonder—why has Annapolis been kept a secret for so long?

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This article is part of Washingtonian’s Visitors’ Guide. For more articles like it, click here.