The bus tours cost forty dollars, sit in traffic, and deliver a commentary you could get from a phone. New York is dense enough that walking is faster than driving for most of Manhattan between eight in the morning and seven at night, and it is the only way to notice anything.
Five routes below. Each takes two to three hours at a sightseeing pace, each ends somewhere you would want to eat, and none of them needs a guide.
1. Lower Manhattan: the seventeenth-century town
Start: Bowling Green (4/5). Finish: Brooklyn Bridge. About 2 hours.
This is the only part of Manhattan that ignores the grid, because it was laid out before the grid existed.
Start at Bowling Green, the city’s first park, a small oval that was a Dutch cattle market. The Charging Bull stands just north of it. Behind you, the old Custom House holds the National Museum of the American Indian, free, in one of the best interiors downtown.
North on Broadway to Trinity Church, whose spire closes the view down Wall Street. Hamilton is in the churchyard.
East along Wall Street — a Dutch stockade line, which is why it bends — past the Stock Exchange façade to Federal Hall, where Washington was inaugurated. Free.
South on Broad Street, which was a canal, then east to Stone Street, a pedestrianised alley of nineteenth-century buildings, and Fraunces Tavern where Washington said goodbye to his officers.
North through the Seaport on the East River — cobbles, Federal-era buildings, tall ships — and finish at the Brooklyn Bridge approach.
2. Greenwich Village: the streets that beat the grid
Start: West 4th St (A/B/C/D/E/F/M). Finish: Union Square. About 2 hours.
Washington Square Park first — the arch, the fountain, the chess tables, and about 20,000 bodies underneath from when it was a potter’s field.
West on Washington Square North past the Row, then into the bent streets: Bedford Street for number 75½, the narrowest house in New York at nine and a half feet; Grove Court, a private mews behind an iron gate; Commerce Street, which bends for no visible reason.
Christopher Street for the Stonewall Inn, a National Monument, and the Gay Liberation Monument in Christopher Park opposite.
North to Jefferson Market Library, a Gothic former courthouse, then east along Bleecker — the folk circuit of the early 1960s — and MacDougal, past the Café Wha?
North through Washington Mews, a cobbled lane of converted stables, and up to Union Square.
3. Midtown Art Deco
Start: Grand Central (4/5/6/7/S). Finish: Columbus Circle. About 2.5 hours.
Grand Central Terminal — the concourse, the backwards ceiling, the whispering gallery, and the dirty patch left uncleaned.
East on 42nd to the Chrysler Building lobby, then back west a few blocks to look at the crown from a distance, which is the only place it reads properly.
New York Public Library and Bryant Park.
North on Fifth to Rockefeller Center via the Channel Gardens, which is how it was designed to be approached. Look at Lee Lawrie’s Atlas facing St Patrick’s Cathedral across the road, and go into the lobby of 30 Rock for the Sert murals.
West to Radio City, then north on Sixth or through the Fifth Avenue shops to Grand Army Plaza and Columbus Circle.
4. The Brooklyn waterfront
Start: High St (A/C). Finish: Atlantic Avenue. About 2.5 hours.
Down into DUMBO for the Washington Street view of the Manhattan Bridge, the Belgian block streets, and Jane’s Carousel.
South along Brooklyn Bridge Park — 1.3 miles of former shipping piers, with the Granite Prospect on Pier 1 giving the best free skyline view in the city.
Climb to the Brooklyn Heights Promenade at any of the stairs, and walk it north to south, cantilevered over the expressway.
Into Brooklyn Heights — America’s first historic district, brownstones from the 1820s. Plymouth Church on Orange Street, a station on the Underground Railroad.
Finish on Montague Street or continue south to Atlantic Avenue for the Middle Eastern food shops.
5. Harlem
Start: 125th St (2/3). Finish: 145th St. About 2 hours.
125th Street east to west: the Apollo Theater, the Studio Museum, the Adam Clayton Powell Jr. State Office Building.
North on Malcolm X Boulevard to the Schomburg Center — free, and its exhibitions are serious. Langston Hughes’s ashes are under the lobby floor.
Strivers’ Row — West 138th and 139th between Adam Clayton Powell and Frederick Douglass Boulevards. Row houses from 1891 by three architects including Stanford White, and the best domestic architecture in Manhattan north of the Village. The rear alleys still have signs reading “Private Road, Walk Your Horses.”
North into Sugar Hill, where Duke Ellington and Thurgood Marshall lived, and finish at the Morris-Jumel Mansion at 160th if you have the legs — 1765, the oldest house in Manhattan, and Washington’s headquarters in 1776.
Eat on Frederick Douglass Boulevard or at Sylvia’s on Lenox.
Practical
Twenty blocks is a mile north–south. Crosstown blocks are roughly three times as long as they look on a map.
Ten to twelve miles a day is a normal New York sightseeing total, which is more walking than most people do in a week at home. Shoes matter more than anything else you pack.
Public toilets barely exist. Use museums, department stores, hotel lobbies, Bryant Park and chain coffee shops, and go when you see one.
Crossing the road: most avenues and streets are one way, so traffic comes from a single direction, and it is often not the one your instinct expects. Cyclists go the wrong way down one-way streets constantly and quietly.