Staten Island: Staten Island Ferry
Manhattan: South Street Seaport Museum
Bronx: Mike's Deli
Queens: Gantry Plaza State Park
Brooklyn: The Pencil Factory
1 You can’t call yourself a true New Yorker until you’ve set foot in every single borough—and it’s possible to cross all five off in one daylong trek. Start off by cruising across New York Harbor on the Staten Island Ferry (South St at Whitehall St, siferry.com), from which you can marvel at sights like the Statue of Liberty. After disembarking, hang a right on Richmond Terrace to amble through St. George’s small historic district. A pretty stretch is St. Marks Place between Nicholas Street and Westervelt Avenue, where the stately mansions date to the late 19th century.
2 Catch the ferry back to Manhattan and walk along the East River waterfront from Battery Park to the recently reopened South Street Seaport Museum (12 Fulton St between South and Water Sts; 212-748-8600, seany.org) to learn how New Yorkers used to traverse the boroughs. The film installation “Time and Tide” captures waterfront scenes dating as far back as 1903.
3 Head to the Fulton St subway and prepare for a haul up to the Bronx. (Transfer from the 4 to the D at Yankee Stadium, and get out at Fordham Rd.) A 20-minute walk gives you time to work up an appetite: The Italian-American wonderland around Arthur Avenue is teeming with shops selling cured meats, pastries and other goodies. Stop by Mike’s Deli (2344 Arthur Ave between Crescent Ave and E 187th St, 718-295-5033) for the Big Vinny’s Favorite ($8.25), a sub overstuffed with ricotta salata, sopresatta and roasted peppers.
4 Hop back on the D at the Fordham Rd stop and—after a quick transfer to the 7 at Bryant Park—cross the river to Long Island City, where Gantry Plaza State Park (48th Ave at the East River, 718-786-6385) awaits. After a brief tour around the reclaimed massive gantries—which were used to move railroad cars from barges—take a load off on a wooden chaise lounge.
5 Drag yourself off of your perch—you’re almost finished!—and walk along 49th Avenue to the Pulaski Bridge, which connects Long Island City and Greenpoint. Admire the view of midtown before heading onto the historically Polish end of Manhattan Avenue. Tuck into a plate of specialties such as pierogi ($6), kielbasa ($8) and stuffed cabbage ($6.50) at Karczma (136 Greenpoint Ave between Franklin St and Manhattan Ave, karczmabrooklyn.com) before straggling to local bar The Pencil Factory (142 Franklin St at Greenpoint Ave, pencilfactorybar.com). Have a seat at one of the wooden tables and raise a glass to seeing more of the city in one day than many do in a lifetime.