Winter Is Coming: Now Is the Time to Start Planning
I know… Fall literally started just yesterday. Thinking about where you’ll be sipping a cocktail in January or wandering through a Christmas market in December might be the last thing on your mind.
But when it comes to travel, winter really isn’t that far away.
If a November getaway, holiday trip, or post-holiday escape is on your mind, now is the time to start planning for Winter 2026–27. And no, that doesn’t mean you need every dinner reservation and excursion figured out today. It means getting the important pieces in place while you still have choices.
The best hotels, preferred room categories, convenient flights, private tours, and those little extras that can turn a good vacation into an incredible one don’t always stick around.
So, where should you go? Several destinations are already gaining plenty of attention for 2026 travel, and these are some of my favorites for the winter months.
November: The Underrated Time to Get Away
November might be one of my favorite months for a city-focused trip. The summer crowds have disappeared from many destinations, temperatures are more comfortable, and you can often experience a completely different side of a city.
Rome, Italy is a perfect example. Imagine long lunches, incredible hotels, evenings with a glass of wine, and exploring the city without the intensity of the summer heat. Rome continues to be one of the most sought-after international destinations, and November gives you an opportunity to experience it at a slower pace and without the crowds that the summer brings.
For something completely different, there’s Bangkok, Thailand, which has emerged as one of the most-booked cities for 2026 travel. Bangkok is a fantastic choice if you love incredible food, beautiful luxury hotels, culture, shopping, and a trip that feels truly different from your everyday life. It’s also an easy starting point for a larger Thailand itinerary.
Madrid, Spain is another city I think deserves more attention, especially for travelers who have already checked Paris or Rome off their lists. Add Lisbon, Portugal, Buenos Aires, Argentina, and Marrakech, Morocco, and November suddenly gives you some very interesting possibilities.
Marrakech in particular is one to watch. Gorgeous riads, beautiful resorts, rooftop dinners, private guides, spas, markets and desert experiences make it a great choice for travelers looking for something luxurious without choosing the traditional European vacation. Also, the temperatures are comfortable in November for top tier exploring.
December: Lean Into the Holidays (or Escape Them)
December gives you two completely different ways to travel.
You can fully embrace the holiday season in places like London, Paris, Tokyo, Vienna, and New York City. Think Christmas markets, decorated hotels, holiday afternoon teas, festive dinners, shopping, lights and all of those experiences that somehow feel even better in December.
If a European Christmas market has been sitting on your travel wish list, Vienna would be high on mine. And this is exactly the type of trip where planning ahead matters. Location, hotel choice and the experiences you build around your stay can completely change the trip. Plus, you can make a whole trip of Christmas markets if you would like by starting in Vienna and making your way to Germany and Brusssels.
But maybe your idea of December has absolutely nothing to do with coats and Christmas markets.
In that case, let’s talk about St. Lucia.
St. Lucia has been seeing a major increase in traveler interest, and it’s easy to understand why. This is the kind of Caribbean trip where I would lean into the experience: a beautiful resort, a room with a view, private transfers, a boat day, spa time, and absolutely nowhere you have to be.
Sometimes luxury is a five-star hotel. Sometimes it’s simply waking up and having no idea what day it is. Or sometimes, it’s both.
January: Escape Winter Completely
By January, I am firmly in the camp of going somewhere warm (even though I live in Florida now, the North East is still in my bones).
Dubai is an obvious choice for travelers looking for sunshine with a serious luxury factor. Beautiful resorts, beach clubs, incredible restaurants, shopping and over-the-top experiences make winter one of the best times to experience the city. It is also one of the most comfortable times of the year (temperature wise) to visit, which is a big deal over there.
If you want something closer to home, Nassau, Bahamas makes for an easy escape. Whether that means Atlantis, Baha Mar, or a quieter luxury experience, you can be on a beach without committing to a major long-haul trip.
For travelers who want food, culture and city life instead of a resort, Mexico City is one of my favorites on this list. Stay somewhere beautiful, plan a few incredible meals, explore the neighborhoods and museums, and build in enough time to actually enjoy the city instead of racing through a checklist.
And then there are the bigger January adventures.
Cape Town, South Africa is in the middle of summer. Costa Rica combines volcanoes, rainforest, wildlife, hot springs and the beach into one trip. And Cartagena, Colombia brings together Caribbean weather, colorful architecture, history, great food and beautiful hotels. And, it is closer to the United States than many would think!
These are the kinds of trips that can make January feel a lot less like January, which we all know is the longest month of the year.
Why Start Planning Now?
Because luxury travel isn’t just about choosing the most expensive hotel.
To me, luxury is having options.
It’s getting the room category you actually wanted. It’s taking the nonstop flight instead of piecing together an inconvenient itinerary. It’s having the private guide available on the day that makes sense. It’s securing the restaurant you were excited about, arranging seamless transportation, and creating an itinerary that has enough structure to make things easy without scheduling every minute of your vacation.
The earlier we start, the more opportunities we have to make those choices.
You don't necessarily need to book every component of your Winter 2026–27 vacation today. But if you're considering traveling in November, December or January, now is the time to start the conversation.
Because the best trips usually aren't the ones we throw together at the last minute.
They're the ones where all the little details come together so seamlessly that, once you arrive, all you have to do is enjoy them.
Thinking about a winter escape? Let’s start planning.