Annapolis is:

The answer, obviously, is ‘e.’ While Maryland’s capital is worth visiting year-round, Annapolis really shines in summer, when its 17 miles of shoreline, longstanding boating culture and devotion to Chesapeake seafood come fully alive. In just two hours from home, you could be picking through a tray of spice-crusted blues, overlooking the pontoons and sailboats drifting by on the water. Start the car.

Raspberry-peach scones zigzagged with icing, strawberry-rhubarb galette, and other warm-weather pastries line the counter at Curate, a beloved five-year-old cafe (and adjacent bottle shop) on West Street. Whether you want to start your Annapolis trip with a quick cappuccino and white chocolate-ube muffin, or something heartier like the quiche filled with corn, zucchini and feta, Curate’s got you covered for your first stop in town.

📍 141 West St., Suite 101, Annapolis, Md. 21401

Conveniently positioned between the waterfront and the Naval Academy campus, 134 Prince has only five rooms within its 19th-century manor house. Original wood floors, brick fireplaces, and built-in cabinetry sets a historic backdrop, but this isn’t some doily-covered relic. The crisp linens, clean lines, and quiet neutrals of the suites keep things feeling fresh rather than dusty.

📍 134 Prince George St., Annapolis, Md. 21401

The Naval Academy is inseparable from Annapolis itself. While visitors can’t just roll up to classrooms or training exercises, the U.S. Naval Academy Museum offers a glimpse into the world with its collection of model ships, battle artifacts, naval paintings, and wreck treasures, including items from the USS Saginaw, a retired warship that got wrecked on a reef near Hawaii in 1870.

📍 118 Maryland Ave., Annapolis, Md. 21402

The public almost lost access to Greenbury Point Conservation Area, a biodiverse peninsula where the Severn River and Mill Creek empty into the Chesapeake, when the Navy wanted to turn it into a golf course. Maryland’s congresspeople kiboshed that plan, and the tranquil preserve remains open to all. Start at the nature center, where the trails roll out from, and bring binoculars for spotting bald eagles, double-crested cormorants, blue herons, and more.

📍 Greenbury Point Nature Center, Annapolis, Md. 21402

You can’t go to Annapolis and not get out on the water, but given very few of us travel with our twin-masted sailboats, you’ll be able to catch a ride on Woodwind and Woodwind II. These sister vessels have multiple daily departures through summer from the Annapolis yacht harbor into the Chesapeake Both have bars onboard, which means sunset cocktails are handled. Visiting during the week instead of the weekend? Book a ticket for the weekly Wednesday-night race, when dozens of boats fill the bay for a wind-powered regatta.

📍 80 Compromise St., Annapolis, Md. 21401

A general store in the 1920s, a bar since the ‘40s, and in its current iteration since 1986, Davis’ Pub is a touchstone of the Eastpoint neighborhood. Lacrosse gloves and hockey masks dangle from the open rafters. Neon beer signs and Orioles memorabilia color the walls. And the crowd is an easygoing mix of locals, boaters, crab tourists, Naval Academy staff, and visiting parents. The food’s great — especially the Chesapeake Bay Retriever hot dog loaded with crab dip — but this is really about grabbing a Natty Boh and soaking up the room.

📍 400 Chester Ave., Annapolis, Md. 21403

We’d contest there’s no better place in the world to sit and pick crabs than a butcher paper-covered picnic table on the back deck at Cantler’s Riverside Inn. Located on Mill Creek, a scenic residential inlet of the Chesapeake, the crabhouse has been steaming blues since 1974 and maintains the feel of a low-key neighborhood joint (cherry wood bar, drop ceilings, church-hall chairs). Soft pretzels come topped with broiled crab dip, and pots of mussels overflow, but of course the hard shells are the raison d’etre. The crustacean, whose daily sizes and prices are listed on a chalkboard, arrive blasted with J.O. Spice, the lesser known (but more locally popular) Old Bay analog. Ask for sides of butter and vinegar and settle in. No finer Annapolis evening exists.

📍 458 Forest Beach Rd., Annapolis, Md. 21409