The affluent neighbourhood of Georgetown seems to have stood the test of time, maybe due to the fact that it’s completely inaccessible by DC Metro.
Hop in an Uber and ask to be dropped off at the Chesapeake and Ohio Canal (or C+O Canal to locals) for a serene stroll down by the Potomac River.
Afterwards, head over to historic Clyde’s of Georgetown on M Street for brunch and a Bloody Mary.
Post-brunch, pop into Martin’s Tavern on Wisconsin Avenue, to see the booth where then-senator John F. Kennedy popped the question to Jacqueline Bouvier in 1953.
The couple lived in Georgetown during the years before JFK became president.
Georgetown is also one of DC’s best neighbourhoods for shopping, sporting boutiques that would impress even the most discerning fashionista.
Hit up AllSaints for butter-soft leather jackets, Billy Reid for styles from the deep-south and if you can’t commit, visit one of the few brick-and-mortar locations of web-based Rent the Runway.
Later, spend the twilight hours strolling the picturesque grounds of Georgetown University, the oldest Catholic and Jesuit university in the United States.