New York City

Manhattan is a grid above 14th Street: numbered streets run east–west, avenues north–south, so addresses are self-explanatory once you know that Fifth Avenue splits east from west. Below 14th, the older street plan in the West Village, SoHo and the Financial District wanders, which is exactly why those areas are the nicest to walk.

Think in clusters. Lower Manhattan covers the 9/11 Memorial, Wall Street, the Staten Island Ferry and Chinatown. Midtown holds the postcard set: Grand Central, the Empire State Building, Bryant Park, Times Square, and the theatres. Upper East and West Sides flank Central Park and hold the big museums. Brooklyn (DUMBO, Williamsburg, Park Slope) is where you get the skyline views and a slower pace, and it is 15 minutes on the subway, not a day trip.

Base yourself in the East or West Village, Chelsea, Lower East Side or Brooklyn Heights / Williamsburg for a neighbourhood you would actually eat dinner in. Midtown is convenient and characterless; near Times Square is the one area worth avoiding for a hotel.

For the view, Top of the Rock beats the Empire State Building because it looks at the Empire State Building, with Central Park behind it. Summit One Vanderbilt is the mirrored, theatrical option; Edge at Hudson Yards is the outdoor ledge. Book a slot around 45 minutes before sunset and you get daylight and night from one ticket.

Central Park deserves half a day on foot: the Bethesda Terrace and Bow Bridge, the Ramble, Belvedere Castle, the Reservoir loop. The High Line works best walked south from 34th Street down to the Whitney, ending in the Meatpacking District for dinner.

The Staten Island Ferry is free and passes the Statue of Liberty; take it if you only want the photo. Pay for the ferry to Liberty Island and Ellis Island if you want the immigration museum, which is the more moving half of the trip. The 9/11 Memorial pools are free to visit; the museum below is heavy and excellent, and needs a couple of hours.

Times Square takes ten minutes. See it at night, once, then leave.

The Met is the one unmissable museum, and it is too big to finish: pick three wings (Egyptian, European paintings, the American Wing) and stop. The MoMA is compact and dense with famous 20th-century work. The American Museum of Natural History is the pick with children. Smaller and often better: the Frick, the Whitney, the Tenement Museum on the Lower East Side, and the Noguchi Museum in Queens.

For Broadway, the TKTS booth still sells same-day discounts, and most shows run their own digital lotteries and rush tickets, which are the cheapest legitimate route to a hit. Off-Broadway is smaller, cheaper and often more interesting. For live music, look at the Village Vanguard or Smalls for jazz, and Brooklyn venues for everything else.

You can eat brilliantly here for $5 or $500. The cheap end is the good end: a bagel with cream cheese or lox for breakfast, pizza by the slice, dollar-ish dumplings in Chinatown, a pastrami on rye at Katz's split between two people, halal cart chicken over rice at 2am, and the tacos and tortas of Sunset Park and Jackson Heights.

Queens is the single best eating borough in the country: Flushing for regional Chinese, Jackson Heights for Indian, Nepali and Colombian, Astoria for Greek and Egyptian. One subway ride, no reservation needed.

For anything notable at dinner, book two to four weeks out and take the 5:30pm or 9:45pm slots when the prime times are gone. Bar seats at good restaurants are often walk-in only, which is the reliable trick. Tipping is 18-20% and sales tax is added at the till, so mentally add roughly 30% to menu prices.

The subway runs 24 hours and is the fastest way to move. Tap a contactless card or phone at the turnstile with OMNY; fares cap automatically after 12 rides in a week, so no pass is needed. Check whether your train is local or express, and expect weekend reroutes.

Walk more than you plan to. Twenty blocks north–south is about a mile and takes 15-20 minutes, which is usually faster than a cab in Midtown. Buses are useful crosstown. Yellow cabs and rideshares are fine at night; the airport journeys are the ones worth pre-planning.

From JFK, the AirTrain plus the subway or LIRR is cheapest and reliable. Newark has AirTrain plus NJ Transit into Penn Station. LaGuardia has no train, so use the Q70 bus to the subway, or a cab. All three can take 60-90 minutes door to door in traffic.

September to early November is the best stretch: warm days, clear light, autumn colour in the park, and the cultural season starting. April to early June is the other good window. July and August are humid and heavy, though the city empties slightly and hotel rates soften. January and February are cold and grey but cheapest, and the museums are at their most pleasant.

Christmas through New Year is beautiful and completely full: the Rockefeller tree, the store windows, the skating rinks, and prices to match. Book months ahead if that is the trip you want.

Budget-wise, accommodation is the pain point, and hotel rooms are small for the money. Sights add up quickly, so consider a pass only if you genuinely plan four or more paid attractions. Many museums have suggested-donation or pay-what-you-wish hours, and the best days here cost almost nothing.

Four full days covers a first visit without rushing; five or six lets you add Brooklyn and Queens properly. If you want more of the region afterwards, the Florida guide is the easy winter-sun follow-on, and Washington DC, Boston and Philadelphia are all a few hours by train.