From snow-covered mountain lodges to Caribbean beaches, a little flexibility can open up some wonderful possibilities for Christmas and New Year’s travel.
The festive season is one of my favorite times of year to travel. Hotels take on a different atmosphere, families find time to be together, and familiar destinations have a way of feeling entirely new.
It is also a season that requires a lot more planning and strategy.
Christmas and New Year’s are among the most sought-after travel periods of the year, and many of the world’s leading hotels operate with different booking requirements during these weeks. Minimum stays are longer, arrival dates may be restricted, and the most desirable accommodations are often reserved well in advance.
But you can approach festive travel in ways that open up possibilities, especially if you have some flexibility with your dates. I’ve enjoyed looking back at my December travels over the years: chasing the sun in the BVI with Gil, and family skiing in the Spanish Pyrenees.
Following our recent conversations with hotel partners at Virtuoso Travel Week, the RTLM team has been revisiting some of our favorite destinations for the holidays, from the mountains of the American West and Switzerland to the beaches of Mexico and the Caribbean.
Here is where we would start.
Understanding the Festive Season
In the hotel world, the festive season generally refers to the peak holiday period surrounding Christmas and New Year’s, although the exact dates and booking policies vary by property.
At popular ski resorts, five-night minimum stays are common during peak holiday periods. Warm-weather resorts in Mexico and the Caribbean frequently require seven nights or longer, particularly for stays spanning Christmas and New Year’s.
Some properties also have fixed arrival and departure dates, while others apply different minimums to specific room categories or private residences.
This is why searching for a few nights over Christmas can produce surprisingly limited results, even when a hotel has rooms available for a longer stay. Knowing how these booking patterns work gives us more ways to approach the trip.
Consider Leaving Before the Christmas Rush
One of the first things I suggest is looking a little earlier.
Traveling earlier in December can put you ahead of the biggest Christmas arrivals. Depending on the property, those dates may also give us more flexibility with length of stay and accommodation options.
For families who have some flexibility around school schedules, a few days can make a meaningful difference.
It won’t automatically eliminate festive minimum stays, but it gives us another set of dates to work with.
Make January the Holiday
If your schedule allows, consider traveling just after the New Year.
Many holiday guests begin heading home after New Year’s Day, and some hotels transition out of their peak booking periods. That can mean greater flexibility with length of stay and accommodation options.
This timing is particularly good for couples who would rather celebrate New Year’s at home and depart when everyone else is returning to reality.
Don’t Get Too Attached to One Destination or Hotel
This is probably my biggest piece of advice for festive travel: decide what matters most first.
If the entire family wants to ski, we can look at several mountain destinations. If the priority is a villa where three generations can spend Christmas together, that gives us another set of options. If you are a couple looking for somewhere quiet and warm, we should start there.
Flexibility with dates and destinations gives us much more to work with.
Sometimes the answer is a combination. Spend a few nights in a city before heading to the mountains, arrive at the beach before the Christmas rush, or turn the first week of January into the holiday instead.
Then we can get to the fun part: deciding where to go.
A Winter Holiday Closer to Home
For a traditional ski holiday, Madeline Hotel & Residences, Auberge Collection puts you in Mountain Village in Telluride. Four Seasons Resort and Residences Jackson Hole is another favorite when skiing is the focus of the trip.
If you like the idea of the mountains but don’t necessarily want everyone clipping into skis each morning, The Ranch at Rock Creek in Montana and The Lodge at Blue Sky, Auberge Collection in Utah give you more ways to spend a winter day outdoors.
For couples, Twin Farms in Vermont offers something quieter: individually designed accommodations, snowy countryside and plenty of reason to stay close to the fire.
A Swiss Christmas: Markets, Mountains & the Magic of Winter
For a completely different kind of winter, you can look across the Atlantic. I love Switzerland at this time of year, and Zurich makes an easy starting point.
Zurich + Lucerne
Give yourself a few nights at Mandarin Oriental Savoy, Zurich, right on Paradeplatz, for Christmas markets, shopping and dinners in the city. The markets are scattered throughout Zurich, so you can wander between the stalls in the old town and the Christkindlimarkt at the main train station.
For a softer take on a Swiss winter, continue to Mandarin Oriental Palace, Lucerne.
The hotel is set on Lake Lucerne, giving you the mountains without committing everyone to a full week of skiing. The concierge can arrange a private horse-drawn carriage through the snow, chocolate making, outdoor raclette or a day skiing in Andermatt, Sedrun and Disentis. There is even a visit to a family-run Swiss farm, where children can feed the cows and collect eggs before tasting what the family produces there.
I particularly like this combination for couples or families where some want to ski, and others would be perfectly happy staying closer to the lake.
Zurich + St. Moritz
Go a touch further to St. Moritz for a magical winter wonderland Christmas.
Follow the Christmas Markets Along the Rhine
If Christmas markets are more your speed than ski slopes, continue the journey with Scenic River Cruises. Their festive itineraries bring you from Zurich through Europe’s Christmas-market destinations. Spend your days exploring historic old towns strung with lights and tasting regional festive specialities, then wake up somewhere new the next morning, without packing and unpacking every few days.
A Different Kind of Christmas
Of course, a festive holiday doesn’t have to involve snow. Sometimes it’s good to change things up and go somewhere unexpected.
Amangiri in southern Utah is one of my favorite suggestions for couples looking for privacy and a complete change of scenery. The desert and vast open skies bring their own kind of festive.
In California, Rancho Valencia offers gardens, tennis, and Southern California weather, while San Ysidro Ranch is great for a romantic few days above Santa Barbara. The gardens, private cottages, and foothills setting caught my attention during Virtuoso Travel Week.
Meadowood Napa Valley makes sense for couples who would happily organize the holiday around wine country and good meals.
On the other coast, The Breakers offers the classic Palm Beach Christmas, particularly for families who want warm weather without leaving the US.
And then there is New York. A few nights in the city for restaurants, theater, shopping, and the energy of Christmas in Manhattan can be a trip in itself.
Mexico & the Caribbean: Following the Sunshine
For many of our clients, festive travel means warm weather, a great beach, and the chance to settle into one place for a week or longer.
Mexico and the Caribbean remain important destinations for Christmas and New Year’s, although this is also where those festive booking patterns can become particularly important.
The Riviera Maya, Mexico
The Riviera Maya is a place very close to my heart. I lived here in the early 90s and brought the RTLM Team here for our Festive Team Retreat last December (early in the month, following our own advice!).
The St. Regis Kanai Resort and The Riviera Maya EDITION at Kanai are two properties our team knows both through our relationships with their hotel teams and our own time in the destination.
The two have distinctly different personalities, which gives us options depending on who is traveling and what they want from the holiday. Those hotel relationships also matter during a busy period like festive, when knowing the people looking after our clients gives us another point of contact on the ground.
Cap Maison, St. Lucia
Cap Maison is another property that came onto our festive radar through Virtuoso Travel Week.
Gil Jr. recently spent time with co-owner Rufus Gobat learning more about the resort’s rooms, suites and villas, as well as the experiences available around St. Lucia.
For couples or families who want to combine beach time with getting out and exploring the island, this is one we would investigate.
Grand Cayman
Grand Cayman becomes particularly interesting for foodies, if your dates can extend into January.
The Ritz-Carlton, Grand Cayman hosts Cayman Cookout, its annual culinary event bringing an impressive group of chefs, winemakers and drinks experts to the island. The 2027 lineup includes Eric Ripert, José Andrés, Clare Smyth, Daniel Boulud, Emeril Lagasse and Andrew Zimmern, with a program of tastings, dinners and culinary events that makes January a particularly fun time to be in Grand Cayman.
A Relaxed Festive
For many couples, the goal is to escape the larger family resorts altogether. Somewhere private, with a great beach, long lunches and enough space to feel quiet even during one of the busiest travel periods of the year.
Hermitage Bay in Antigua is one of the first places I would consider. It is adults-only, small in scale, and set along its own bay. The all-inclusive format also makes things wonderfully easy once you arrive.
Baoase in Curaçao has just 23 accommodations, many with private pools, and feels more intimate than a traditional Caribbean resort. It does welcome families, so I think of it as couples-oriented rather than adults-only.
For even greater privacy, Guana Island in the British Virgin Islands offers a private-island escape where the sea and the island itself set the pace.
On Mexico’s Pacific coast, Naviva, A Four Seasons Resort takes the idea in another direction. There are just 15 tented bungalows spread across 48 acres of coastal jungle near Punta Mita. It is adults-only, with days centered around nature, wellness, food and time outdoors.
And then there is Cayo Espanto in Belize. Seven villas. One private island. It isn’t adults-only, but the scale makes it particularly appealing for couples who want to disappear for a few days.
For Bringing the Whole Family Together
Grandparents, adult children, grandchildren, siblings and cousins can quickly turn a festive hotel booking into a logistical exercise. This is when villas take center stage.
A great villa gives everyone somewhere to retreat while keeping the family together for the parts of the holiday that matter: Christmas morning, long lunches and evenings around the same table.
Jumby Bay Island, Antigua
For a multigenerational Caribbean holiday, Jumby Bay Island is one of the first places I would look.
The private island has substantial villas and residences alongside the hotel, so a family can have its own home while still enjoying the resort’s restaurants, beaches, and activities.
Everyone can come together when they want to, disappear when they don’t, and nobody has to cook unless they particularly feel like it.
Oil Nut Bay, British Virgin Islands
Oil Nut Bay on Virgin Gorda is another option when the villa itself is an important part of the holiday.
The accommodations range from smaller villas to large private homes, making it possible to find something that suits the size and shape of the family traveling.
Some may want to spend the day on the water, while others are perfectly happy by the pool. Everyone comes back together at the house.
Four Seasons Resort Peninsula Papagayo, Costa Rica
For active families, I would look at Four Seasons Resort Peninsula Papagayo in Costa Rica.
Its private residences include multi-bedroom homes with kitchens, private pools and generous indoor-outdoor living spaces, while the family still has access to the wider Four Seasons resort.
Costa Rica also gives you plenty to do beyond the villa, which matters when several generations are traveling together and nobody has quite the same definition of a good day.
The RTLM Take: Start With Who Is Coming
Before choosing the destination, start with the people.
Are you taking the children and grandparents somewhere everyone can be together? Are you a couple looking for a quiet beach away from the larger family resorts? Does everyone want to ski until the lifts close, or would half the family rather meet for lunch?
Once we know that, the list gets much shorter.
Dates matter too. If Christmas week isn’t fitting neatly, look a little earlier. If New Year’s is proving difficult, consider the first days of January and make the beginning of the year your holiday instead.
Festive availability moves quickly, and minimum stays vary from one property and room category to another. Rather than forcing your dates into a hotel that doesn’t quite work, start with who is traveling, where you have flexibility and how you actually want to spend the holidays.
Then we can work our magic.
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