Category: Big-City Itineraries

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Big American cities reward a plan. The subway map, the museum queues and the one neighborhood that deserves a full afternoon are the difference between a trip that flows and one spent in transit. Every guide in this section is a day-by-day itinerary for first-time visitors, built around real walking distances, sensible neighborhood bases and the stops that are worth the time.

You will find routes for New York, Los Angeles, Chicago, Las Vegas, Miami, Orlando, Boston and San Diego, each with where to stay, how to get around without a car where that is possible, and what to skip. If a city is on your list for a long weekend, start with the four-day version and trim from there.

Two things hold true across almost every big US city. First, the best base is rarely the most famous neighborhood: in New York a stay near a good subway line beats a tiny room in Times Square, and in Los Angeles you pick an area for the drives you will actually do. Second, the shortest realistic stay is three nights, because the first half day goes to arrival and the last to leaving.

If you are comparing cities for a first big-city trip, New York gives the densest sightseeing, Chicago the best architecture and food for the price, Las Vegas the easiest short break, and Miami and San Diego the best mix of city and beach.

Start with: New York City itinerary, Chicago itinerary, Las Vegas itinerary, Miami itinerary

Part of USA Destinations & National Parks guides. Browse the other topics there to keep planning.