The Best Cities for Winter Sun
Ten places at their best between November and March, none of them a beach resort — and one at the bottom of the world where December is summer.
Winter sun usually means a beach and a wristband. These are cities and towns instead — places you'd want to walk around anyway, that happen to be at their best in the northern winter because that's their dry season.
Mexico is the deepest bench. Mérida and the Yucatán are dry and warm from November to March, before the heat builds in spring. Oaxaca's best months run from October to December, which also means its markets, mezcal and Day of the Dead fall inside them. San Miguel de Allende and Mexico City sit high on the central plateau: bright, dry days through the winter, cold enough after dark that you'll want a jacket, which surprises people every year.
Havana and Trinidad share Cuba's dry season, November to April, most of it after the hurricane season ends on 30 November. Go knowing that Cuba is in a hard place: power cuts and shortages mean hours change without notice, so confirm what matters the day before.
Chiang Mai and the mountain town of Pai are at their best in northern Thailand's cool, dry months from November to January or February. Go early in that window: from around February, crop burning across the region brings smoke haze that can last into April. Palm Springs is the American version — desert, mid-century architecture and a winter season that's the whole point of the place.
Puerto Natales is the odd one out. It's the gateway town to Torres del Paine in Chilean Patagonia, and its season runs November to March for the opposite reason to the rest of this list: down there, that's summer.
Merida
A pastel colonial capital that calls itself the safest city in Mexico, with cantinas older than the claim.
Oaxaca
Seven moles, a market that smells of chocolate and chillies, and mezcal from people who will show you the still.
San Miguel de Allende
A hill town smaller and quieter than its postcard pink church spire suggests, with a food scene out of proportion to its size.
Mexico City
Too large to see in one trip, so most people pick a neighborhood and live in it for a few days.
Havana
Paladares at the top of crumbling mansions, rumba on Sunday afternoons, and an ice-cream cathedral that opens when there's ice cream.
Trinidad
A sugar-boom colonial town of cobbles and pastel houses, where the local drink comes in a clay pot.
Chiang Mai
A walled old town ringed by villages that are still villages.
Pai
A small mountain town in Mae Hong Son that slows down on its own terms.
Palm Springs
A midcentury desert resort town two hours east of LA, built around pools, golf, and mountain views.
Puerto Natales
A working port on the Señoret Channel that exists mostly as the last stop before Torres del Paine, two hours north.