Midshipmen in Annapolis are not the town’s only snappy dressers. An hour east of Washington, Annapolis is a good place for a shopping day trip.
Take a tip from a local and stop first at Weekend Living (167-G Jennifer Rd., 410-571-1555; weekend-living.com), across from Annapolis Mall (take the Parole exit). It stocks hip lines like Diane von Furstenberg, prep classics by CK Bradley, and a large selection of housewares and jewelry.
Then head downtown via West Street. In this up-and-coming area, you’ll find Astrid (175 West St., 410-626-9726), which carries impossible-to-find Australian designer Aurelio Costarella.
Keep walking toward Main Street and you’ll come across locally designed jewelry and affordable handbags at Lilac Bijoux (145 Main St., 410-263-3309; lilacbijoux.com). Other good stops are Diva (30 Market Space, 410-280-9195; modadiva.com), for trendy women’s apparel, and Zachary’s (100 Main St., 410-266-5555; zacharysjewelers.com) for sparkly gems. Prepsters love the Lilly Pulitzer store the Pink Crab (16 Market Space, 410-216-9994; thepinkcrab.com).
Stroll through the gates of the US Naval Academy (with a photo ID) and glimpse tailored sailors on your way to boutiques like Sitting Pretty (35 Maryland Ave., 410-267-1722; shopsittingpretty.com), with its Milly party dresses and decadent cashmere sweaters. Browse hot home-decor items at Vie Necessary Luxuries (86 Maryland Ave., 410-269-6100) or the tchotchkes at nationally known artist Natalie Silitch (66 Maryland Ave., 410-263-7177; nataliesilitch.com).
Johnson’s (79 Maryland Ave., 410-263-6390; johnsonsontheavenue.com) is famous for its naval uniforms and yachting apparel, and trendsters shouldn’t miss Madison Boutique (47 Maryland Ave., 410 -295-7878).
Hungry? Annapolis Ice Cream Company (196 Main St., 443-482-3895; annapolisicecream.com) has to-die-for flavors like apple pie and s’mores. For more of a meal, try Asian fusion at Tsunami (51 West St., 410-990-9868), a great steak at Lewnes’ (401 Fourth St., 410-263-1617; lewnessteakhouse.com), or oysters at local favorite McGarvey’s (8 Market Space, 410-263-5700; www.mcgarveyssaloon.com). A short boat or taxi ride away are steamed crabs at Jimmy Cantler’s Riverside Inn (458 Forest Beach Rd., 410-757-1311; cantlers.com).