If you’re looking for some romanticism to write home about, tap into the storybook charms of downtown Manhattan and Brooklyn Heights.
9:30 a.m.: Wake up to old-fashioned eats. Tuck into omelettes ($13$16) or blueberry-packed pancakes ($15) at Friend of a Farmer, a country-inn restaurant on picturesque Irving Place, off Gramercy Park. In summer, request a seat outside; in winter, snuggle up to one of two working fireplaces.
10:30 a.m.: Relive a movie moment. After picking up some farm-fresh fruit or baked goods at the Union Square Greenmarket (Mondays, Wednesdays, Fridays, and Saturdays), walk one block west to Fifth Avenue, then hang a left until you reach the arch in Washington Square Park. It’s time for your When Harry Met Sally moment.
11:30 a.m.: Get in touch with Village history. Go west on Waverly Place, then take a left on Seventh Avenue until you hit Bleecker Street. (Detour on tiny Jones Street to reenact the arm-in-arm cover of Bob Dylan’s Freewheelin' album.) On Bleecker (familiar to anyone who’s watched Sex and the City), continue west before looping south on Hudson Street, home to St. Luke's garden. Just beyond the “St. Luke’s School” sign is a footpath leading to a well-tended green spacea spot made for stolen kisses or, if you’re really feeling it, a proposal.
1:30 p.m.: While away some time near Wall Street. By cab or subway, haul down to lower Manhattan for lunch at Financier Patisserie on Stone Street, a pedestrian lane that’s part New York, part European town square. Sit outside while the raucous Wall Street traders spill out of nearby pubs and wine bars. We recommend the Fraisier ($4.50)—a French pastry of vanilla biscuits, fresh strawberries, and Grand Marnier–infused mousse—for dessert.
3 p.m.: Take in views of New York Harbor. Stroll through Battery Park, which lines the southern perimeter of Manhattan, then tuck into the Dead Rabbit for a specialty cocktail—it’s a world-class cocktail joint, boutique beer bar, and familial Celtic pub, all under one roof.
7 p.m.: Cross the river to the River Café. Back at sea level, take a fifteen-minute ride on the New York Water Taxi to Brooklyn. You can pick up one of the company’s checkered yellow boats at Slip 6 in Battery Park, then motor around the tip of Manhattan to Fulton Ferry Landing. Dine on lobster, caviar, and handmade chocolates at the legendary River Café, which sits prettily under the Brooklyn Bridge. (Call ahead for a reservation.)
9 p.m.: Make the most of the moon over Manhattan. Take a postprandial stroll along the Brooklyn Heights Promenade (it’s uphill, but only ten minutes away). Once there, you can enjoy the unbeatable Gotham skyline from the city’s most perfectly placed walkway.