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Sightsee in Style

Well-heeled visitors can spend the morning browsing interesting shops on Maryland Avenue, such as Vie Necessary Luxuries (86 Maryland Ave.; 410-269-6100) and Bailey’s Maryland Avenue (62 Maryland Ave.; 410-280-8845). Then loosen your belt with a cut of prime beef at Lewnes’ Steakhouse (401 Fourth St.; 410-263-1617) before catching the sunset on the Schooner Woodwind (80 Compromise St.; 410-263-7837) as it sails the Chesapeake.

Past Meets Present

Let the Colonial-dressed guides at Watermark Tours (410-268-7601) lead you through historic Annapolis, around the US Naval Academy, and into the Maryland State House. Switch from cobblestones to contemporary cuisine with dinner at Hell Point Seafood (12 Dock St.; 410-990-9888) before catching a live music act at Rams Head Tavern (33 West St.; 410-268-4545).

A Day on the Water

Learn the sailing ropes in a weekend course at J World Annapolis (213 Eastern Ave.; 410-280-2040) or reel in the big one at Megabite Charters (410-721-3386), 30 minutes away in Edgewater. For dinner, head to Cantler’s Riverside Inn (458 Forest Beach Rd.; 410-757-1311) for the capital’s best blue crabs.

Bring the Kids

Arrgh! Step aboard the Sea Gypsy with Pirate Adventures on the Chesapeake (311 Third St.; 410-263-0002), where children don eye patches and hunt for hidden treasure on the weekends. Then grab a bite at the casual, kid-friendly Boatyard Bar & Grill (400 Fourth St.; 410-216-6206). Finally, head to Storm Bros. Ice Cream Factory (130 Dock St.; 410-263-3376) for a cone, sundae, or float.

This article first appeared in the October 2009 issue of The Washingtonian. For more articles from that issue, click here.