Ask anyone outside of the Mid-Atlantic to name the capital of Maryland, and they’ll probably tell you all about Baltimore. But they’re wrong — the capital is the historic waterfront city of Annapolis, home to the United States Naval Academy, the United States Powerboat (and Sailboat) Shows, blue crabs galore and taverns so old, George Washington once drank in them. But the city of 38,000 has much more to offer than sailing ships and nattily attired midshipmen. An easy weekend escape from cities such as Washington, D.C., Richmond or Philadelphia, Annapolis offers waterfront dining, drinking, shopping and culture aplenty.
Be sure to make your reservations in the heart of the historic city’s downtown. The only hotel on the Chesapeake Bay is the Annapolis Marriott Waterfront, and it happens to be one of the nicest as well, fresh from a $1.6 million upgrade that just finished in May of this year, bringing a redesigned lobby, fresh linens and nautical design touches to the hotel. Request the water view rooms with a balcony to take full advantage of your location. Trend seekers might also consider the Westin Annapolis hotel in the up-and-coming West Street neighborhood, located within walking distance from the city’s trendiest restaurants and bars such as Rams Head Tavern and Metropolitan Kitchen & Lounge.
From either hotel, walking around downtown is a breeze, but you can also keep the car parked and utilize the complimentary downtown shuttle from the Westin if you’d prefer to spend a bit less time on foot. Start your first day at the City Dock at the foot of Main Street. Pause to take in “Ego Alley,” named for the size of the boats docking at the harbor. Walk up Main, browsing local boutiques like Horse, which offers designer names for women such as Parker, Rebecca Taylor and Tibi, or local favorite Laurance Clothing for men — think Peter Millar and Vineyard Vines, perfect for fitting in with Annapolis’ preppy, sailing chic style.
Re-fuel along the way at Walter and Nancy Giera’s Annapolis Ice Cream Company — the Mint Oreo and Apple Pie are standout flavors, all made in house. Take your cone or cup to go and wind your way around Church Circle at the top of Main and head past historic St. John’s College to Maryland Avenue. If you wish, pause on the lawn and recall one of the area’s most eagerly anticipated annual events, a croquet match between the midshipmen of the Naval Academy and the liberal arts “Johnnies” of St. John’s. Browse along the design boutiques and art galleries before heading back to your hotel for a cocktail or brief rest.
But don’t linger too long. It’s time to hop in a cab or your car and head across the bridge for a crab picking at Jimmy Cantler’s Riverside Inn, a local favorite for steamed hard-shell crabs, or, if you prefer a more fine dining atmosphere, a martini and fresh seafood at the Severn Inn. Sit in the bar for a more casual atmosphere and spectacular sunset views. The Asian tapas plate appetizer with tuna sashimi, crab spring roll, spicy tuna roll and crispy calamari is a must-try.
Start day two with a coffee and your walking shoes. You’ll want to stroll through some of the city’s historic sites, such as the William Paca House and its stunning summer garden ($10 for adults) or the Naval Academy, where you can enjoy a public tour ($10 for adults, $8 for children) that includes a visit to the crypt of Revolutionary War hero John Paul Jones. If you can, try to catch a daily “formation,” where the entire crowd of nearly 4,000 Midshipmen assembles before lunchtime.
Then, the day is yours. If you want to head out on the water, try one of the Watermark Cruises; a 40-minute excursion ($14 for adults, $6 for children) leaves just about every hour from the city dock and cruises along the Annapolis harbor. Bring your camera to snap pictures of the area’s native blue herons, the massive cruisers that dock at the Annapolis Yacht Club and the majestic Chesapeake Bay Bridge. If you’re an experienced yachtsman, use South River Boat Rentals to pilot your own vessel, powered by your choice of motor or sail (rates start at $160). Prefer a landlubbers’ excursion? A 20-minute drive lands you at the area’s first casino, Maryland Live!, which, as of mid-April, offers table games. Attached to the area’s largest outlet mall, Arundel Mills, the vibrant and new casino is a must visit. But skip dinner at the mall; instead, head back for a local’s night out.
The small plates and cocktails (don’t miss the pizzas) at the intimate Vin 909 are always a hit, and the restaurant is a short cab ride from either hotel. If being on the water or at the tables has given you more of an appetite, try the clubby Lewnes Steakhouse (a local destination since 1921) instead, where you’ll find perfectly-charred steaks and shareable side dishes like crisped pommes frites. Or, opt for another night of seafood at the much-loved O’Learys, where you’ll want to try the local delicacy, Rockfish, served whole with herbs, garlic and Kalamata olives.
From there, the night is yours. Westin guests should end with a nightcap at one of the popular bars along the strip by the hotel. Level is a safe bet for cocktails made with fresh local herbs; try the Peach Basil Collins, with Old Tom gin, peach, basil, lemon sour mix and a splash of soda. Marriott guests can sip a signature “Painkiller,” a mixture of rum and fruit juice, at Pusser’s Caribbean Grille, the dock bar in the hotel.
Photos Courtesy of Annapolis Marriott Waterfront Hotel, iStock/KevinMarlowe, iStock/Michael Bagley