Begin your tour at Columbus Circle, where a monument to Christopher Columbus marks the gateway to the Upper West Side. Discover how this landmark was funded by Italian immigrant communities in the 1890s, setting the tone for a neighbourhood built by ambition and immigrant ingenuity.

Explore the USS Maine National Monument, where the likeness of Audrey Munson, America's first supermodel, appears twice. Learn the tragic story behind this once-celebrated figure whose image became a defining feature of early 20th-century American sculpture.

Walk through Lincoln Center's grand plaza, surrounded by the Metropolitan Opera House, David H. Koch Theater, and David Geffen Hall. Hear how the fictional gang wars of West Side Story were filmed among the rubble of the real neighbourhood demolished to build this extraordinary concentration of performance venues.

Pass the American Museum of Natural History, home to 32 million artefacts spread across more than twenty interconnected buildings. Take in the scale of one of the city's most iconic cultural institutions as you continue along the route.

Stop at the legendary Dakota, where John Lennon lived and died. Hear how even celebrities like Madonna and Cher were turned away by the building's notoriously selective co-op board.

Discover why the Ansonia once kept live seals in its lobby fountain and a farm on its roof. Learn how this extraordinary building attracted residents as varied as Babe Ruth, Igor Stravinsky, Arturo Toscanini, and Bette Midler across very different eras.

Learn how the Metropolitan Opera was founded out of Gilded Age spite, a rivalry that shaped one of the world's great opera houses. Take in its place at the heart of Lincoln Centre's plaza, alongside the David H. Koch Theatre and David Geffen Hall.

Bear right toward the entrance of Tavern on the Green, a landmark destination set inside Central Park itself. Learn how it hosted regulars like Mayor Fiorello La Guardia, Grace Kelly, and Fay Wray, plus neighbour John Lennon, who celebrated his birthday here with Yoko Ono in 1979.

End your tour at Zabar's on Broadway, the legendary New York culinary institution that has been feeding the Upper West Side since 1934. Soak in the atmosphere of this beloved neighbourhood landmark, famous for its smoked fish and old-school charm.