New York City

New York City is the most concentrated urban experience on the planet. The key to a great trip is picking 2–3 neighborhoods and going deep rather than sprinting between landmarks. The best meals and moments will be unplanned — a slice at 2am, a stoop conversation, a subway musician who stops you cold. Plan the skeleton; let the city fill in the rest. Manhattan's neighborhoods have distinct personalities that make repeat visits feel like different cities. The West Village is the most livable-feeling part of Manhattan — brownstones, wine bars, the High Line nearby. Williamsburg in Brooklyn has the best rooftop bars and the densest concentration of interesting food in the five boroughs. The Lower East Side is still the most authentic version of what New York was before the money came back. Chinatown in Manhattan is functional, crowded, and has some of the cheapest good food in the city. The Met, MoMA, the Guggenheim, and the Whitney all deserve time. The 9/11 Memorial Museum is difficult and necessary. Central Park at rush hour during the week is a completely different experience from a Sunday morning — both worth having. The High Line is best on a weekday before the tourist crowds arrive. The subway goes everywhere and runs 24 hours — get a MetroCard or tap a card and use it constantly. Avoid taxis during rush hour; avoid Times Square whenever possible. Spend a morning at the Brooklyn Bridge, a night in the East Village, and at least one hour doing absolutely nothing in a coffee shop.