Boston

Boston is the most British-feeling big city in America and the easiest to do without a car. The historic core is small, flat and walkable: the Freedom Trail draws a literal red line on the pavement past 16 colonial and revolutionary sites, Beacon Hill’s gas lamps and cobbles are a 30-minute photo loop off the Common, and the North End packs the best dinners into a few Italian-American streets. You arrive expecting a fiddly American transfer and instead ride the free Silver Line bus straight in from Logan. The job of a good first trip is to walk most of it, eat in the North End, and not over-plan a city you can cross in an afternoon.

Two to three full days covers Boston comfortably: one for the Freedom Trail and Beacon Hill, one for Harvard and Cambridge across the river, and an evening for the North End. Where it really earns its place is as half of a pairing — fly into Boston, do New England, then take the Amtrak down to New York in three and a half to four hours rather than flying between them. The autumn is the headline draw: early-to-mid October for the foliage day trips out into the hills, though Boston’s own streets often hold their colour later, into early November.

Below, the structured planning — where to stay, the airport options, a realistic budget in pounds, and the autumn timing — picks up from here. Entry rules (the ESTA, why your GHIC is worthless in the US) live on the United States country guide.