Whatever the hour, start your day at Chick & Ruth’s Delly, a stalwart breakfast counter for homemade pies, award-winning crab cakes, and massive platters named after local politicians. (Order the “Congressman Elijah E. Cummings” for a one-pound ham steak, two eggs, potatoes, and toast.)
The best way to get to know “Naptown,” as its locally known, is to go off and explore. Partake in various Watermark walking tours to learn about African-American heritage or ghost lore, or hop aboard a classic Woodwind schooner to admire the city by water. We also recommend meandering the likes of Main Street and Maryland Avenue for historic-home browsing and boutique shopping (especially at McBride Gallery, KA-CHUNK!! Records, and Annebeth’s wine shop).
For your midday meal, it’s all about local seafood. At City Dock, grab a street-side booth at the circa-1740 Middleton Tavern—once patronized by founding fathers George Washington, Thomas Jefferson, and Benjamin Franklin—for people watching, oyster shooters, and lump-filled crab dip. For more world-class crab cakes, try Davis’ Pub in Eastport, while Cantler’s Riverside Inn across the Severn River is your destination for hard shells.
Often called a museum without walls, Annapolis is a history buff’s version of bliss. On State Circle, the Maryland State House once housed the Continental Congress and still serves as the General Assembly’s gathering place today. For more colonial history, saunter through the verdant gardens of the William Paca House and Historic London Town in nearby Edgewater. Of course, no trip is complete without a visit to the U.S. Naval Academy. Before football season rolls around, tour the grounds, museum, and campus chapel, where you can view the crypt of John Paul Jones, aka the father of the U.S. Navy.
To experience the best of the city’s restaurant renaissance, start with happy hour at Sailor Oyster Bar for craft cocktails and fancy takes on fish before moving onto your main course at Preserve. This farm-to-table eatery, featured on our list of 50 Best Restaurants, focuses on sustainable sourcing and seasonal dishes such as grilled Maryland blue catfish or coffee-glazed local beef. Enjoy dessert a few doors up at the Annapolis Ice Cream Company, with homemade flavors including blueberry and Key lime pie.
Live music abounds in Annapolis, with the original Rams Head Tavern featuring premier acts such as Taj Mahal and the Kingston Trio on its intimate stage. (On July 31, catch Baltimore’s own Thomas Dolby of “She Blinded Me With Science” fame.) Also check out the Metropolitan Kitchen & Lounge for up-and-coming artists, and the Annapolis Maritime Museum for summer evening concerts. The Annapolis Summer Garden Theater is another nightlife must, with al frecso plays beneath the stars.