Wisconsin to 18th Street: D.C. by Neighbourhood

Drop your bags at your Georgetown base and get your bearings on the brick-paved streets before the day begins in earnest.

Start the morning in the formal gardens and Byzantine collection at Dumbarton Oaks — a grand 19th-century estate that quietly anchors upper Georgetown. The terraced grounds alone are worth arriving early for.

Walk north up Wisconsin Avenue to the soaring neo-Gothic cathedral that crowns the city's highest ridge. Take your time with the nave's kaleidoscopic rose windows and the tower views over the rooftops stretching back toward the river.

Head back down toward M Street for a relaxed Italian lunch at Pines of Florence — a warm room on M Street Northwest that's worth the short walk from the Georgetown main drag.

Catch a rideshare or the D6 bus east along P Street and drop onto 14th Street NW — the stretch between P and U Street that has become the city's most concentrated dining and culture corridor.

A short detour off the corridor brings you to this remarkable institution — the only major museum in the world dedicated exclusively to women artists. The permanent collection spans five centuries and the building itself, a former Masonic temple, is architecturally striking.

Double back to the 14th Street–Logan Circle neighbourhood and pull up a stool at Stoney's on P Street — a no-frills neighbourhood bar that has anchored this block through every wave of change the corridor has seen.

End the evening with dinner at Via Sophia on 14th Street, one of the corridor's most talked-about Italian-leaning tables. A great place to linger over pasta and wine after a full day on foot.

Start the second day slowly around the Dupont Circle fountain, grabbing coffee from any of the cafés lining Connecticut Avenue before the crowds arrive.

Walk or take a short rideshare down to the Potomac waterfront and the Kennedy Center — D.C.'s great riverside arts palace. The free rooftop terrace offers one of the most arresting views of the river and the Virginia hills beyond, and the Grand Foyer is open to visitors throughout the day.

Back in Dupont Circle, Al Tiramisu on P Street has served neighbourhood regulars and embassy staffers for years with Northern Italian cooking that earns every reservation. A proper sit-down lunch — the kind that makes the afternoon feel earned.

Head down to the Mall for the Hirshhorn — the Smithsonian's contemporary art museum housed in a striking cylindrical building. The sunken sculpture garden outside is free and endlessly photogenic, and the galleries inside turn over regularly with major modern shows.

Make your way back north to Logan Circle and stop into Cafe Saint-Ex on 14th Street — named for the aviator-author, with a downstairs bar that has the low-lit ease of a good neighbourhood local. A perfect place to decompress before crossing into Adams Morgan.

Walk up Columbia Road into Adams Morgan and take a table at Akira Ramen & Izakaya on 18th Street. The izakaya format — small plates, rich broths, good sake — suits a long final evening perfectly, and the room buzzes without ever feeling frantic.

Finish the trip the way Adams Morgan intended: at Madam's Organ, the neighbourhood's most characterful bar, where live blues and R&B fill the front room most nights. Step in for one last drink and let the music close out the weekend.