‘Tis the Season
Christmas in July and the Secret to Festive Season Travel
Planning the Holidays Before They Plan You
A beautiful display at The Ritz-Carlton Chicago last year.
For all my planners out there, you likely already have your holidays mapped out, and applause to you. 🙂
But if you’re anything like the rest of us, you’re still trying to figure out how to squeeze in one more long weekend before summer is over, let alone whether you’re hosting Thanksgiving, Hanukkah, Christmas, or your annual festive gathering.
As your resident planner, I’m here to tell you that the holiday season has a booking window unlike any other.
In the travel world, we often refer to it as festive season, which is roughly Thanksgiving through New Year’s. It’s when cities put their best decorations forward, Christmas markets and ice skating rinks overtake plazas, and hotels transform their lobbies into destinations all their own. One of my favorite Chicago traditions was spending a Saturday hopping from one beautifully decorated hotel lobby bar to another. Every property tried to outdo the next, and somehow each felt magical in its own way.
It’s also one of my favorite times of year to help clients plan because every family celebrates differently.
Some dream of Christmas markets and midnight Mass in another language. Others want sunshine, a beach chair, and someone else cooking dinner. Some want to gather three generations under one roof. Others are looking for a quiet escape after a busy year.
I love hosting. There’s something incredibly satisfying about setting the table, planning the menu, and welcoming people into your home. But I’ve also learned that traditions don’t have to look the same every year. Some years you have the energy to host. Other years, it’s nice to be the one who’s welcomed. Ironically, experiencing both has made me appreciate each even more.
There’s no “right” holiday destination. There’s only the one that’s right for your family this year.
Why Holiday Travel Books Differently
Unlike summer travel, holiday travel is compressed into a relatively short window. Schools dictate schedules, families often have fixed vacation dates, and everyone is trying to travel at the same time.
That means the first things to disappear aren’t usually flights. The below are the first to go:
The best room categories
Connecting rooms for families
Villas and multi-bedroom accommodations
Christmas and New Year’s dining reservations
Ski instructors
Rental cars
Private guides and festive experiences
Premium airline seats and award availability
If you’re traveling with grandparents, multiple families, or have your heart set on one specific hotel, now is the time to start planning. There are only so many adjoining rooms, suites, villas, and holiday experiences available. Miracles can happen, but having options is much more enjoyable than hoping for one.
The good news? Some properties are already offering early booking promotions for the holiday season. Sea Island, for example, recently released a 25% advance booking offer for select accommodations. The earlier you plan, the more likely you are to find both the room you want and the experience you’ve imagined.
Beside, during this Florida heat, doesn’t a crisp snowfall, a mug of mulled wine, and a cozy turtleneck sound at least a little appealing? After many years of delayed or canceled flights to the Midwest, I’m still #teambeach for Christmas!
What Do You Want the Holidays to Feel Like?
One of the first questions I ask clients isn’t, “Where do you want to go?”
It’s, “What do you want the holidays to feel like?”
The answer almost always leads us to the destination.
If your family loves classic holiday traditions ...
Some families want the kind of Christmas they’ve imagined since they were children.
In NYC years ago in front of Rockefeller Center.
New York City remains iconic for good reason. Between the Rockefeller Center tree, Fifth Avenue holiday windows, Bryant Park Winter Village, the Radio City Christmas Spectacular, and beautifully decorated luxury hotels, the city fully embraces the season. So many properties do Christmas well, but standouts from past trips include The Lotte Palace in Midtown, The Ritz-Carlton NoMad, and The Carlyle on the Upper East Side.
In NYC, the festive atmosphere extends far beyond the famous attractions, it is woven into the entire city.
Across the Atlantic, London transforms into one of Europe’s great holiday destinations (cue one of my favorite holiday movies, Love Actually). Regent Street sparkles overhead, Hyde Park transforms into Winter Wonderland with its giant ice rink and holiday attractions, Fortnum & Mason becomes the spot for afternoon tea, Borough Market is dressed for the season, and evenings at the theatre in the West End, it’s a city that truly embraces the holidays.
It’s also one of those destinations where planning ahead matters. Tickets for holiday performances, special events, and festive hotel packages often sell out months in advance.
For travelers drawn to Christmas markets, Strasbourg’s Christmas market has welcomed visitors since the 16th century, filling the historic center with hundreds of wooden chalets selling handmade ornaments, mulled wine, and Alsatian specialties. Vienna offers an entirely different atmosphere, where markets spill across grand squares in front of the Rathaus and Schönbrunn Palace, making it one of Europe’s most elegant festive destinations.
If togetherness matters more than the destination ...
Some of the best holiday trips aren’t about checking landmarks off a list.
They’re about slowing down.
One of my favorite client trips last December wasn’t international at all. Three generations gathered at Sea Island, Georgia, where mornings began with bike rides beneath the live oaks, afternoons were filled with cooking classes and horseback riding lessons, and evenings ended around the fire pits.
They came home talking less about what they did and more about how relaxed everyone felt. Nobody had to host. Nobody had to cook. Everyone simply got to be together.
Other favorites include Blackberry Farm in Tennessee and The Greenbrier in West Virginia, where exceptional hospitality becomes part of the holiday tradition, which needs at least a 12-month lead time.
If you’d rather trade snow boots for sandals ...
For some families, the perfect holiday means sunshine instead of snow.
St. Barths comes alive during festive season, with beautiful villas, exceptional restaurants, beach clubs, and one of the Caribbean’s most celebrated New Year’s weekends. In Nassau, the highlight of festive season is Junkanoo (December 26-31), a vibrant celebration of Bahamian culture with elaborate costumes, live music, dancing, and late-night street parades.
And if complete relaxation is the goal, and you have the time to travel, the Maldives deliver overwater villas, extraordinary service, and festive celebrations without sacrificing tranquility. Resorts like Four Seasons, Patina, and Soneva create elaborate festive programming around the holidays, but their best villas disappear long before December arrives. This is a bucket-list destination and for good reason!
Closer to home, the ABC islands (Aruba, Bonaire and Curacao) offer a unique European feel outside the hurricane belt. They bring in massive Christmas trees, offer caroling, and celebrate Dutch holiday traditions, making them an appealing option anytime but especially during the holiday season.
If your family loves adventure ...
Holiday travel doesn’t have to revolve around decorations.
The Finnish Lapland is one of the few places that can deliver nearly every childhood winter dream at once: glass igloos, husky sledding, reindeer encounters, and the Northern Lights overhead. Most travelers know Santa’s Village in Rovaniemi, but many of the most special properties sit even farther north, where the skies become the main attraction.
Or perhaps this year’s newsletters have convinced you to consider the American West. Luxury ranches, Jackson, Yellowstone, and Big Sky offer a completely different holiday atmosphere with snow-covered mountains, roaring fireplaces, sleigh rides to dinner, skiing, and days spent outdoors together.
If New Year’s is the celebration...
Some destinations truly come alive as the calendar turns.
Edinburgh’s Hogmanay remains one of the world’s most distinctive New Year’s celebrations, blending concerts, torchlight processions, and centuries-old Scottish traditions. Tokyo offers an entirely different energy, balancing city celebrations with meaningful cultural traditions as one year ends and another begins.
Worth Knowing
One of the biggest misconceptions about holiday travel is that booking early is about getting the best price.
More often, it’s about getting the trip you actually want.
The villa that comfortably fits everyone.
The connecting rooms.
The suite you’ve been dreaming about.
The table for Christmas dinner.
Holiday travel is one of the few times each year where availability and not necessarily price becomes the deciding factor.
Looking Ahead
If holiday travel has been on your mind, July is actually one of the best times to start the conversation.
Even if you’re not ready to book tomorrow, talking through your priorities now gives us the flexibility to find the destination that best matches how you want to celebrate.
Whether that’s strolling through a European Christmas market, gathering the family around a table at Sea Island, celebrating Hanukkah somewhere warm, or welcoming the New Year halfway around the world, the memories created during the holidays have a way of becoming the stories families tell for years.
The earlier we begin planning, the more options we have to create the version that feels exactly right for yours.
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