Occasions
The best US luxury winter escapes
Where to go for a luxury winter trip, whether you want deep snow and a fireside or warm sun and a beach, across the best US destinations for the season.
The short answer
For a US winter escape it comes down to snow or sun. For snow, Aspen, Vail, Telluride, and Jackson Hole lead for world-class skiing and cozy luxury. For sun, Naples, the Florida Keys, and Miami offer warm beaches and blue water while the rest of the country freezes.
Winter splits luxury travelers into two camps, those who chase the snow and those who flee it. The good news is that the US does both exceptionally well.
For snow: the mountain towns
Aspen, Vail, and Telluride in Colorado, and Jackson Hole in Wyoming, are the country's great winter mountain towns: world-class skiing, cozy slopeside luxury, sleigh rides, and fireside dinners. Choose Vail for scale, Aspen for glamour, Telluride for quiet, and Jackson for wild beauty.
For sun: the warm coasts
When the goal is to escape winter entirely, Florida delivers. Naples offers calm Gulf beaches and golf, the Keys bring warm water and days on the boat, and Miami adds energy and nightlife, all while the rest of the country is under a coat.
How to choose
Pick snow if the trip is about activity and cozy evenings, and sun if it is about thawing out and slowing down. Either way, winter is peak season, so the best stays book early.
There are only two kinds of winter trip: the one you take toward the snow, and the one you take to get as far from it as possible.
Tell our planner which winter you are after and it will build a dated escape, the lodge or the beach house, the guides or the boat, sequenced and linked so the season works for you.
Your move
Turn this into a dated, bookable plan
Answer a few questions and get a day-by-day itinerary with a real pick and a booking link for every stay, table, and guide. Founding price, $29.
Common questions
What is the best winter vacation in the US?
For snow, Aspen, Vail, Telluride, and Jackson Hole lead. For sun, Naples, the Florida Keys, and Miami offer the warmest, easiest winter escapes.
Where is warm in the US in winter?
South Florida is the reliable warm-weather escape: Naples, the Florida Keys, and Miami all stay pleasant through winter, which is also their peak season.
When should you book a winter ski trip?
Book the winter holidays and President's Day weeks as far ahead as possible, ideally six months or more, since the best slopeside stays sell out first.
