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.