For a town of only 40,000 people, Annapolis boasts a proud resume: Colonial past, military esteem, world-class sailing. The Chesapeake Bay brought Puritan exiles here in 1649 after they tired of Anglican dominance in Virginia. The Puritans are gone, replaced by Maryland politicos, boaters, sailmakers, Naval Academy midshipmen — and tourists. It’s much busier now than in 1845, when Navy officials established the academy in this “healthy” location, far from “the temptations and distractions” of big cities. The recently renovated Maryland State House — where Gen. George Washington resigned his commission, establishing the democratic principle of civilian control of the military — towers over the town. But the chief attraction is the Chesapeake Bay, formed 35 million years ago, whose shores have sheltered humans for 11,000 years. Today’s visitors to Annapolis can sail the bay’s waters, tour a colonial mansion, enjoy top-notch restaurants and pop into bustling bars. The town is so compact, you may not need your car until it’s time to drive home.

If a helicopter dropped you blindfolded anywhere in Annapolis, your feet would lead you to the water’s edge, at the base of Main Street. So start there, at Ego Alley, a narrow waterway that brings people and shops close to boats (both moored and moving). Check out the sculpture of the writer Alex Haley reading to children. While celebratory, the work also acknowledges a dark era: the selling of Africans arriving by ship. Haley learned that his ancestor, Kunta Kinte, was sold into slavery here in 1767, inspiring his famous book and the miniseries “Roots.” Next, cross Dock Street to get ice cream at Storm Bros., an Annapolis tradition. If the line snakes out the door, don’t fret. You can idly watch Ego Alley’s boaters glide past the tourist crowd (and provide comedy if they can’t manage the tight maneuvering space).

Take the 40-minute narrated cruise on the Harbor Queen excursion boat ($25 for adults, $10 for children, departs hourly), at the end of City Dock, a focal point of downtown that’s lined by restaurants and shops. The narration describes key sights and history — especially of the Naval Academy — as the boat cruises through Spa Creek, the Severn River and a large mooring field where recreational sailboats and powerboats anchor for the night. You’ll get a good view of the four-mile-long Chesapeake Bay Bridge, connecting Maryland’s mainland and Eastern Shore. Frequently, large container ships and tankers are anchored in the bay’s deeper parts, awaiting their opening to steam 30 miles north to Baltimore’s ports to unload and pick up cargo.

Walk a mile across Spa Creek Bridge to Eastport or, better yet, take the Annapolis Water Taxi (from Dock Street, $4). Ask for the Tecumseh stop, then walk to nearby Davis' Pub (4th Street and Chester Avenue). This neighborhood favorite has a water view, local beers and prized soft pretzels slathered with crab dip. For dinner you could try the often-packed Boatyard Bar & Grill, which claims to sell 100,000 crab cakes a year. Admire the countless mounted flags, photos and fish. Burgers are $19; crabcake or swordfish entrees, $36. Or if you prefer a tonier atmosphere, cross the street to O'Learys Seafood, an Annapolis fixture (reservations recommended). The shrimp and grits ($36) are scrumptious, the sea scallops ($46) dandy. The most popular dish is the combo of crispy rockfish (Maryland striped bass) and crab cake ($46).

Take the water taxi back to City Dock and stroll to one of Main Street’s many bars. For a great nighttime view of Ego Alley and the harbor, choose the Choptank. One of the town’s newer and more gleaming spots, it has bars and outdoor seating on two roomy waterfront levels. For a wider choice of whiskeys and other spirits, try Dry 85. They offer more than 60 bourbons, and about as many ryes. One of Main Street’s liveliest spots is easily overlooked. Fox's Den is just a narrow door on the street. But downstairs you’ll find a big, buzzy space with a bar and tables shared by locals and out-of-towners. While regulars dine on pizza from the wood-fired oven, you can focus on the beers, wines and bourbons.

Boating on Spa Creek at sunset. The creek flows through Annapolis and into the Chesapeake at the mouth of the Severn River.

OK, here’s the deal: You don’t go to Chick & Ruth's delly (as they spell it) for memorable food. You go for the kitsch and tradition. This narrow, nearly claustrophobic institution is famous for being stubbornly famous. It’s been churning out breakfasts, lunches and dinners for 60 years, long after its founders, Chick and Ruth Levitt, passed away. Sandwiches are named for state politicians, including those who went to prison. Each morning, around 9:30, a staffer leads the room in the Pledge of Allegiance. You don’t have to stand, but everyone does. (You’re next to the U.S. Naval Academy, after all.) Go for the all-day breakfast, and keep it simple (unless you simply must have a crab cake and waffles for $30). They don’t take reservations, and the line is sometimes out the door.

Tour the Maryland State House (free with photo ID). See where George Washington resigned his commission. Plaques will tell you the building’s top — assembled with wooden pegs, not nails — is the nation’s largest wooden dome. Maryland legislators still convene here January through April. In the floor, look for ancient snail fossils that were embedded in the stone eons ago and included by builders to highlight Maryland’s coastal geology. Next, walk to the nearby Banneker-Douglass-Tubman Museum, which celebrates African American History (free; closed Sundays). Harriet Tubman’s name was recently added to those of the scientist Benjamin Banneker and the abolitionist Frederick Douglass. Tiny but worthwhile, the museum in 2025 features works by the Washington-based multi-media artist Jabari Jefferson. His website says he searches local communities for discarded items and “believes in the transfer of energy in the materials from their previous owners.”

You’re in the self-proclaimed Sailing Capital of America, so join the fun with a two-hour sail on a 74-foot schooner, the Woodwind (or its sister, Woodwind II), which can accommodate up to 48 passengers. Leaving from the Annapolis Waterfront Hotel’s dock several times a day, the boat will cruise past the Naval Academy before venturing into the bay. Depending on the wind, it might head north toward (and possibly under) the Chesapeake Bay Bridge. Or it might turn south, toward Thomas Point Lighthouse, still active after 150 years. Smaller sailboats often race on weekends, and your captain will take care not to hinder them. Passengers can help hoist the sails and even steer. Here’s your chance to learn some sailing basics: Why are you heading this way if your ultimate goal is over there? What’s the difference between tacking and jibing? Tickets are $79.65 on Saturdays, $75.25 on Sundays.

Once you’re back on land, take a five-minute walk to the U.S. Naval Academy (free with photo ID). Tour the visitor center, Preble Hall museum and the main Chapel, which includes the crypt of the Navy icon John Paul Jones. The fun YouTube video Naptown Funk, which has great street scenes of Annapolis, informs us that undergraduates are called midshipmen, or mids, not cadets. The Chapel is handsome, even if the mids no longer must attend Sunday services. One of the stained-glass windows depicts the future disciples Peter and Andrew mending their nets, awaiting Jesus’s call to become “fishers of men.” The Levy Center and Jewish Chapel “supports the moral development of midshipmen.”

Take the town’s free purple-pink shuttle bus up West Street to Sailor Oyster Bar for the best raw bivalves in town, and a yummy smoked white fish dip with crackers. The atmosphere is warm, the beer is cold. For dinner, walk a few doors farther up West Street to Leo Annapolis. The owners Brian and Hilarey Leonard opened this restaurant two years ago, procuring meats and produce from local suppliers — and oysters and scallops from the Chesapeake — whenever possible. The Oysters Rockefeller ($27), smash burger ($19), ricotta gnocchi ($27), coulotte steak ($36) and fried grits ($10) won’t disappoint. Try the citrus-marinated beet salad ($17), and the “Best Days of Our Lives” bourbon cocktail ($14) from the handsomely stocked bar. Reservations recommended.

Take the shuttle bus (or stroll, it’s downhill) back toward the water. For a quiet after-dinner coffee, dessert or nightcap, stop by 49 West. They often have local musicians in the cozy back room. For a louder, rowdier scene, try Stan and Joe's Saloon. The free, live bands start at 9:45. For bigger-name concerts, check the calendar in advance for the Rams Head on Stage. The 2025 summer lineup includes the Smithereens, Kasey Chambers, Orleans and tribute bands to Steely Dan and Billy Joel. Prices vary. Even if you don’t see the stage acts, the adjacent Rams Head bar and restaurant is one of Annapolis’s biggest and most popular bar scenes.

Members of the Annapolis Living Historians participate in “A Garden Party with the Pacas,” a reenactment at the William Paca House & Garden.

After a latte and pastry at one of the town’s many coffee shops, head to the historic William Paca House & Garden. Paca — who signed the Declaration of Independence and was Maryland’s third governor — helped design the impressive home built in the 1760s. Restoration began in 1965, and it’s now a National Historic Landmark. Guides describe a typical day for the wealthy owners, middle-class craftsmen and enslaved servants who intermingled in the house. The two-acre garden has terraced landscapes with boxwoods, a latticework bridge over a fish-shaped pond, a wilderness section and a two-story summer house. A guided tour of the house and access to the garden is $12 for adults, $7 for children. Garden access only is $5.

Now that you have traversed Main Street a few times, duck into some of its shops that offer art, Irish goods, dresses, fudge, sailing gear, and countless gifts and T-shirts. Mills Fine Wine and Spirits has good selections, knowledgeable staffers and frequent tastings. On a street where businesses often come and go, Hats in the Belfry has thrived for 46 years by selling, yes, hats, emphasizing those designed and made in Italy. Similarly impressive, McBride Gallery has been selling paintings, sculptures and other artworks — some featuring local nautical scenes — at 215 Main for four decades. Sailors and landlubbers can lust after the latest jackets and other gear for foul or fair weather — and conduct a battle of the brands — by bouncing between Helly Hansen and Musto, only three doors apart. A few steps off Main Street, at 40 State Circle, the Annapolis Pottery has good selections, including Chesapeake-inspired chowder bowls and various pieces with images of crabs, scallops and other sea creatures.