New York City

New York is the destination clients most often under-plan, on the assumption that it's a city and cities sort themselves out. They mostly do, but Manhattan is 21km long, the subway is excellent but not always intuitive to first-timers, and a day built around 'Midtown in the morning, Brooklyn in the afternoon' loses an hour or more just moving between them. I ask clients to pick two or three neighbourhoods a day and let the rest go, rather than chasing a list that spans the whole island - it's the single biggest difference between a trip that feels frantic and one that doesn't.

Weather shapes the trip more than people expect from a temperate-sounding city. Summer is genuinely hot and humid, with July highs regularly near 30°C and enough haze that skyline views from open-air observation decks can disappoint; winter is properly cold, with wind off the rivers making it feel colder still, but it's also when the city is at its most atmospheric, around the holidays especially. Spring and autumn are the reliable sweet spot - April/May and late September/October give comfortable walking weather without summer's crowds at the big-ticket sights.

December is the one month that breaks the usual crowd logic: it's cold, but Rockefeller Center, the holiday windows on Fifth Avenue, and the general atmosphere pull in enough visitors that hotel rates and sight lines both get squeezed, on top of the summer peak. For a first trip I usually route it as Midtown/Downtown (3 nights) covering the Empire State Building, 9/11 Memorial, and Broadway, then a couple of days split between Central Park/Upper Manhattan and Brooklyn - and I always ask about mobility and stamina up front, since this is a trip built on walking and stairs more than most city breaks.