The 12 Trips of Christmas: Where to Spend the Holidays
By Addie Bell Zackon, Founder & CEO, Jetset & Travel
I'll let you in on a little secret: the holiday trips I plan for clients almost never start with a destination. They start with a feeling. "We want snow." "We want the whole family together and nobody fighting over bathrooms." "We want to be somewhere nobody can find us." "We want to be OUT at midnight."
This year, instead of handing you a list of hotels, I put together 12 completely different ways to spend the holidays, with 5 properties I love for each one. Think of it as the 12 Trips of Christmas.
Before you dive in, I want to share one thing I tell all my clients - December is the most request travel month of the year and many properties require 5-, 7- or 10-night minimums over Christmas and New Year's. The earlier you start the process, the better chance we have of securing the exact vacation you're looking for.
If something here catches your eye, please reach out on our inquiry form! INQUIRE HERE
Where Should You Go for Sun Over the Holidays?
For anyone who would happily trade sweaters for swimsuits. This is a sandy Christmas instead of a snowy one, at properties that still go all in on the season, so it genuinely feels like the holidays. Best for: families and couples who want sunshine without giving up the holiday spirit.
Four Seasons Resort Anguilla | Meads Bay, Anguilla
The largest luxury resort on the island and, in my opinion, the BEST service on Anguilla. Beachfront villas run up to 5 bedrooms for the whole crew, while couples can slip away to the adults-only Sunset Pool, where the swim-up bar comes to you. Christmas here means 2 of the Caribbean's best beaches and nowhere you have to be. (More in my full Anguilla guide.)
Amanyara | Providenciales, Turks & Caicos
Couples take the Pavilions, families take the villas, and the villas are where Amanyara really separates itself. The 3- to 6-bedroom villas come with a dedicated villa host, a private chef and a black infinity pool, and the Artists Villa sits on 3 acres with a 108-foot pool over the water. For a warm Christmas with total privacy, it's hard to beat.
Susurros del CorazΓ³n, Auberge Resorts Collection | Punta Mita, Mexico
We stayed here a couple of years ago, and the multi-bedroom villas make it work for families and couples alike. December is dry season on this stretch of the Pacific, which means tiered ocean-facing pools, surf safaris in the morning, and one of the best swim-up bars we've found at ANY resort.
Four Seasons Cabo Del Sol | Los Cabos, Mexico
Hands down the best overall hotel in Cabo right now, and December is when Cabo's weather is at its most reliable. Oceanfront villas for the family, dramatic infinity pools and world-class golf for the couples, all in a modern hacienda where the desert runs straight into the Sea of Cortez.
Nekajui, a Ritz-Carlton Reserve | Peninsula Papagayo, Costa Rica
The first Ritz-Carlton Reserve in the Americas, perched on a clifftop above the Pacific just as Guanacaste's dry season begins. Villas are reached by a wooden suspension bridge across a ravine, and there's a 27,000-square-foot spa, a funicular down to the beach club, and treetop tented suites if you want the jungle a little closer.
What Are the Best Ski Resorts for Christmas?
This is the holiday that looks exactly like the movies: snow-covered villages, fireside afternoons and festive dinners after a full day on the mountain. One tip from experience: ski-in/ski-out access matters more over Christmas week than any other week of the year, and kids' lessons and rentals are the very first things to sell out. Best for: active families and anyone who wants Christmas to look like Christmas.
The Little Nell | Aspen, Colorado
Aspen's only 5-star, 5-diamond, ski-in/ski-out hotel, and my go-to when clients want to step off Ajax and straight into an award-winning wine cellar. The ski concierge handles your gear, and at Christmas the après scene at the base is the liveliest in a town that's already at its most festive.
Montage Deer Valley | Park City, Utah
We live 10 minutes away and take ANY excuse to go. It's grand and warm at the same time, the food on property is excellent, and the holiday programming is worth planning your trip around. True ski-in/ski-out on Deer Valley, and the ski butlers might be the best feature of the whole place.
Airelles Courchevel | Courchevel, France
An Austro-Hungarian-inspired palace that drops you directly onto Les Trois VallΓ©es, one of the largest ski areas in the world. The ski valet warms your boots before you're even awake, and the La Mer spa and Michelin-level dining take care of everything after the lifts close.
Aman Rosa Alpina | San Cassiano, Dolomites, Italy
Aman's first European ski lodge, tucked into a snow-covered Dolomites village with the brand's signature quiet built right in. The full Dolomiti Superski network by day, 3-Michelin-starred St. Hubertus by night.
Badrutt's Palace Hotel | St. Moritz, Switzerland
The gold standard for a glamorous Swiss ski holiday, towering over a frozen lake with white-glove service, an indoor infinity pool and a nightclub downstairs. Direct access to Corviglia by day, and the high-society holiday galas St. Moritz is famous for by night.
Where Should a Multigenerational Family Go for Christmas?
When everyone is coming, the setup matters just as much as the destination. Space is the real amenity here (connecting rooms, multi-bedroom villas, estate homes), along with kids' programming that's actually good, so the grown-ups get a holiday too. Best for: groups of 8 or more traveling together.
Four Seasons Resort HualΔlai | Kailua-Kona, Hawaii
We stayed here on our babymoon in April, and if you're traveling with little ones, this is the clear winner on the Big Island: an elevated kids' club, strong family programming, and multi-bedroom and connecting room options. 6 restaurants and 7 pools mean nobody has to agree on where to spend the day, and King's Pond lets you snorkel above a resident manta ray! (We compared it head-to-head with its neighbor in our HualΔlai vs. Kona Village guide.)
Montage Palmetto Bluff | Bluffton, South Carolina
20,000 acres of Lowcountry with cottages and multi-bedroom homes, and a Christmas program that turns the whole village into an event: tree lighting, carriage rides and a visit from Santa. December here is mild rather than cold, which makes it the rare holiday trip that needs no long-haul flight and no parkas.
The Alpina Gstaad | Gstaad, Switzerland
Perched above one of the last truly traditional Alpine villages, with connecting family suites, a Six Senses spa for the grown-ups and a private cinema for the afternoon everyone needs off the mountain. Gstaad at Christmas means horse-drawn sleighs and a car-free village center. It's about as close to a storybook holiday as Europe gets.
Four Seasons Resort Costa Rica at Peninsula Papagayo | Peninsula Papagayo, Costa Rica
2 beaches on a lush isthmus, with canopy suites and multi-bedroom residences for the whole family. Adventure for every age is built right into the week: ziplining through monkey-filled jungle, ATV trail rides, surf school, catamaran days and an Arnold Palmer golf course.
A Private Villa, Anywhere
We have access to spectacular villas all over the world, and for a multigenerational holiday they solve the problem hotels can't: everyone sleeps under one roof, and everyone still gets their own space. Many come staffed with a private chef, a butler and a concierge to build the week around your family's traditions, and where they don't, we can arrange all of it.
Where Can You Go for a Quiet, Festive Holiday Without Skiing?
Some holidays are meant for doing less. These are the places for roaring fires, long breakfasts, snow outside the window and the kind of week where staying in feels like the entire point. No skiing required! Best for: couples and families who want quiet over spectacle.
Estelle Manor | Oxfordshire, England
A castle on 3,000 acres of English parkland, and the closest thing to a Christmas card I know. Roaring log fires, a Roman-inspired bathhouse and billiards rooms built for exactly this time of year.
Wildflower Farms, Auberge Resorts Collection | Hudson Valley, New York
I stayed here solo and exhaled the moment I arrived: freestanding cabins with floor-to-ceiling windows, NO TVs anywhere, and a fire going in the lobby as the sun sets over the fields. Book the Ridge Cottage for the valley views and private fire pit, and whatever you do, don't skip the bread-making class or the cinnamon roll at Clay. (Read about my full stay here.)
The Resort at Paws Up | Greenough, Montana
37,000 acres of working cattle ranch with private luxury homes and stone fireplaces you can hear crackling from the next room. Sleigh rides, snowmobiling and gourmet winter dining under a very big sky.
Gleneagles | Perthshire, Scotland
Known as the "Riviera in the Highlands," and in winter it's all tartan interiors, roaring fires and Michelin-starred dining. A world-class spa, 3 championship golf courses and endless country pursuits for when you do want to venture outside.
Fairmont Chateau Lake Louise | Alberta, Canada
We were here last January, and if you want to feel like you're standing inside a snow globe, THIS is the place. Skate on the frozen lake, take a horse-drawn sleigh ride, then have afternoon tea facing the Victoria Glacier.
What Are the Most Remote Luxury Hotels for Christmas?
Some trips are about being unreachable. Helicopter-only access, private glaciers, islands with no roads and Northern Lights over total silence: the complete opposite of a crowded lobby. The journey becomes part of the experience here. Best for: travelers who've done it all and want somewhere almost nobody else has been.
Eleven Experience: Deplar Farm | Troll Peninsula, Iceland
A former sheep farm turned ultra-luxe lodge at the edge of the Arctic Circle, with turf roofs, heli-skiing and a geothermal pool with a swim-up bar. Long winter nights here mean front-row seats to the Northern Lights.
Sheldon Chalet | Denali National Park, Alaska
A hexagonal chalet perched on a rocky outcrop inside a glacial amphitheater, reachable ONLY by helicopter. Private glacier treks, gourmet Alaskan cooking, and stargazing with nothing else around for miles.
Fogo Island Inn | Fogo Island, Newfoundland
An architectural landmark rising off the North Atlantic, reached by ferry, with ocean views from every handcrafted suite. Wood-fired saunas, rooftop stargazing tubs and a genuinely immersive local culture on an island most people have never heard of.
Miavana by Time + Tide | Nosy Ankao, Madagascar
A helicopter-access private island with oceanfront villas and private wildlife safaris by air. Lemur trekking and untouched coral reefs, a world away from the winter crowds.
The Brando | Tetiaroa, French Polynesia
Marlon Brando's private atoll, reached by small plane from Tahiti, now a pioneering eco-resort with private pool villas tucked into the palm forest. Off-the-grid luxury with reef snorkeling, deep-sea fishing and complete privacy.
Where Is the Best Place to Spend New Year's Eve?
Not everyone wants a quiet New Year. This is the trip built around midnight, not the 25th: dressing up, staying out and waking up on January 1 with a very good story. One honest note: New Year's inventory is the first thing to go every year. Best for: couples and friend groups who want the party.
Cheval Blanc St-Barth | St. BarthΓ©lemy
Directly on Flamands Beach, where French Riviera polish meets Caribbean energy. New Year's is the peak of St. Barts' superyacht season, and this is the anchor for the island's legendary celebrations.
Faena Miami Beach | Miami Beach, Florida
Sexy, vibey and totally theatrical: the whole property feels like a cabaret, and I'm calling the vibe "velvet rope, but make it beachfront." Red velvet, gold leaf, Los Fuegos, and New Year's revelry on the sand that runs until sunrise.
HΓ΄tel de Paris Monte-Carlo | Monaco
Right on Casino Square, with Le Louis XV and wine cellars worth the trip alone. Supercars out front, high-stakes tables inside, and Mediterranean fireworks at midnight.
Atlantis The Royal | Dubai, United Arab Emirates
A gravity-defying build on the Palm Jumeirah with 17 restaurants and a 90-meter sky pool. Purpose-built for a big New Year's, with front-row views of Dubai's world-famous fireworks.
Wynn Tower Suites | Las Vegas, Nevada
Our favorite in Vegas! A hotel-within-a-hotel with its own private entrance and dedicated concierge team. It's the quiet launchpad for the loudest night of the year, with nightclub access, incredible dining and midnight on the Strip.
Which European Cities Have the Best Christmas Markets?
The most traditionally festive trip on this entire list. Mulled wine, twinkling stalls and snow-dusted old towns. Here's the part people don't realize: most markets run from late November through early January, so you don't have to travel on Christmas Day to experience them. Best for: couples and culture-driven travelers.
Four Seasons Hotel Prague | Prague, Czech Republic
4 buildings dating back to 1568, united on the bank of the Vltava with Prague Castle and the Charles Bridge right out the window. The Old Town Square market and the country's tallest Christmas tree are a 7-minute walk away, and the concierge team arranges private market tours and antique-car rides through the Old Town.
Hotel Sacher Salzburg | Salzburg, Austria
Old-world Austrian grandeur on the Salzach River, with the original Sacher-Torte waiting downstairs. You're steps from the Altstadt markets and the Christmas concerts that fill the city every December.
Rosewood Schloss Fuschl | Hof bei Salzburg, Austria
A 15th-century castle on the shore of Lake Fuschl, 20 minutes outside Salzburg. Lake views and forest walks by day, and the Salzburg Christkindlmarkt just a short drive away.
Four Seasons Hotel Gresham Palace | Budapest, Hungary
An Art Nouveau palace on the Danube at the Chain Bridge, steps from the VΓΆrΓΆsmarty Square and St. Stephen's Basilica markets. Chimney cake and mulled wine outside, and a Champagne countdown in the lobby bar on New Year's Eve.
Mandarin Oriental, Vienna | Vienna, Austria
Mandarin Oriental's Austrian debut, opened in late 2025 inside a restored 1908 Art Nouveau courthouse in the First District, walkable to the Stephansplatz market and the State Opera. After a day in the cold, the subterranean spa's 43-foot heated pool is one of very few hotel pools in the city (fun fact: the crew uncovered Roman remains while digging it!).
What Are the Best Cities to Visit at Christmas?
Holiday windows, lobby trees, ice rinks and world-class dining. A city Christmas is perfect for a shorter trip (you really don't need a full week), and it's easy to combine with family visits. Best for: shorter getaways and travelers who want to walk everywhere.
The Plaza | New York City
A New York institution on Central Park South, and we've seen firsthand how they go all out for Christmas. The lobby tree, the Palm Court, the park across the street and the Fifth Avenue windows out the front door. It's the New York Christmas you've pictured your whole life.
The Mark | New York City
Downtown energy on the Upper East Side, with Jean-Georges in the lobby, Madison Avenue right outside and Central Park a short walk away. The suites are among the largest in the city, which matters when the whole family is in town for the holidays.
Claridge's | London, England
Mayfair Art Deco, famous for its designer-curated lobby Christmas tree, which has become an event of its own. Liveried footmen, roaring fires and the West End's holiday lights at your door.
Four Seasons Hotel George V | Paris, France
My favorite property in Paris, full stop. I stayed here during the holiday season and honestly did NOT want to check out. Jeff Leatham's winter floral installations are unreal, there are 3 Michelin-starred restaurants, and the Eiffel Tower views are everything. Going to Paris is always a good idea, but going at Christmas is an ESPECIALLY good idea.
Raffles Singapore | Singapore
A grand colonial classic with 24-hour suite butlers and the famous Long Bar. It's a warm-weather take on the big city Christmas, with festive light displays all down Orchard Road.
Can You Rent a Private Island for Christmas?
You absolutely can. The whole island, 1 group and complete privacy. Just know booking works a little differently here: these are buyouts, arranged by request rather than a click, and holiday dates get claimed well in advance. Best for: milestone celebrations and larger groups who want total seclusion.
Fregate Island Private | Seychelles
Cliffside pool villas above some of the Indian Ocean's most dramatic beaches, on a protected ecological haven you'll share with no one but your group. Fully bespoke, with dedicated butlers and giant tortoises roaming the island.
Necker Island | British Virgin Islands
Richard Branson's 74-acre estate, with a Great House, Balinese-style villas and an endless fleet of water toys. A full buyout hosts up to 48 guests, which makes it one of the few islands built for a truly big holiday gathering. Resident lemurs included!
Moskito Island | British Virgin Islands
125 acres of distinct private estates, each with its own infinity pools, entertaining spaces and staff. Total privacy for your group, plus shared tennis courts, water sports and a beach house for when you want company.
Laucala Island | Fiji
3,200 acres of volcanic terrain with private residences, a championship golf course and (yes, really) a glass-bottom submarine. Wild Fijian jungle, a lagoon-style pool and a 5:1 staff-to-guest ratio.
Royal Island | Eleuthera, Bahamas
430 private acres designed for just 1 group at a time, with 5 beachfront bungalows and a central beach club. Private chef, jet-ski adventures and deep-sea fishing on your schedule.
Is a Yacht a Good Idea for the Holidays?
If you want to wake up somewhere new every morning without repacking a single suitcase, yes! Two quick things to know. Hotel-brand yachts and private charters are two very different trips, and winter charter season is the Caribbean. The Mediterranean is off-season this time of year, so save it for summer. Best for: travelers who want to see several places in one trip.
The Ritz-Carlton Yacht Collection | At Sea
We've sailed her, and she delivers exactly what she promises: all-terrace suites, an onboard spa, and dining that holds up against any hotel. For a holiday that changes views every morning, she anchors in boutique harbors the big ships simply can't reach. (Here's our firsthand experience aboard.)
Four Seasons Yacht (Four Seasons I) | At Sea
Residential suites with floor-to-ceiling windows and private terraces, bringing Four Seasons service to open water. A transverse marina puts the ocean right at your feet, so holiday days can be spent swimming and paddleboarding straight off the yacht.
Orient Express Corinthian | At Sea
A tribute to the golden age of travel: towering masts, opulent maritime interiors and a glass-bottomed pool. For couples who want the holidays to feel like pure romance, with cutting-edge sailing technology underneath.
Amangati | At Sea
Aman's first yacht, with just 47 suites, an Aman Spa and a 2-story serenity garden. Honest note: Amangati doesn't set sail until Spring 2027, so this is a conversation for NEXT holiday season.
Private Charter | Caribbean Sea
A fully crewed superyacht where you set the menu and the map. Hidden coves across the BVI, the Bahamas and the Grenadines, and a Christmas dinner on deck with nobody but your people.
What Are the Best Luxury All-Inclusive Resorts for the Holidays?
One rate, no decisions and no bill at the end of dinner. Luxury all-inclusive is a completely different category than it used to be! One honest distinction, though: 3 of these are truly all-inclusive, while Blackberry Farm and Amangiri are full board, meaning your meals are covered but alcohol, spa and guided activities are extra. Still wonderful, just good to know going in. Best for: families who want the holiday without the logistics.
Jumby Bay Island, Oetker Collection | Antigua
A car-free, 300-acre private island where the golf carts, the bicycles, the water sports and every meal are simply part of the stay. Estate homes with household staff, and calm, shallow water for the little ones.
Blackberry Farm | Walland, Tennessee
A 4,200-acre working farm in the Great Smoky Mountains with its own creamery, bakery and charcuterie, where 3 meals a day come with your room and the food is the entire point. Book a Hill Cottage for the indoor-outdoor fireplace.
Grand Velas Los Cabos | Cabo San Lucas, Mexico
Proof that all-inclusive and ultra-luxury aren't opposites! 7 restaurants including the Michelin-starred Cocina de Autor, 1,100-square-foot suites with private plunge pools, and a kids' club families come back for year after year. Top-shelf spirits and airport transfers are all part of one rate.
Ambergris Cay | Turks & Caicos
A 1,100-acre private island 20 minutes by plane from Providenciales, with the flight included in your stay. Beachfront bungalows for couples, 3- to 6-bedroom villas for groups, and Γ la carte dining, top-shelf drinks and non-motorized water sports all included.
Amangiri | Canyon Point, Utah
34 stone suites built into a protected desert valley, with the Grand Staircase-Escalante out every window and all 3 meals included. Camp Sarika next door adds 10 tented pavilions with private plunge pools if you want the desert even closer. (Guided excursions are extra and worth planning ahead.)
Where Should You Go for a Completely Different Holiday?
For the family that's done the traditional holiday and is ready for something new. Omakase instead of turkey, onsen baths instead of eggnog, or a summer Christmas in the Southern Hemisphere. This is the trip people talk about for a decade. Best for: repeat travelers ready to shake things up.
The Ritz-Carlton Reserve, Higashiyama | Niseko, Japan
Just 50 rooms, with private onsen baths, Mount Yotei out the window and ski-in/ski-out access to Niseko's famous powder. Trade the turkey for omakase and soak while the snow falls.
Aman Kyoto | Kyoto, Japan
A secret forest garden at the foot of Mount Hidari Daimonji, with private onsens and cedar soaking tubs. Moss-covered pathways, Zen quiet and traditional kaiseki dining, about as far from a traditional Christmas as you can get.
Amanpuri | Phuket, Thailand
Aman's very first resort, on a private peninsula in a coconut grove above the Andaman Sea. Secluded beaches, holistic wellness and world-class Thai cooking in place of the holiday ham.
Southern Ocean Lodge | Kangaroo Island, Australia
Rebuilt on coastal cliffs, with floor-to-ceiling wilderness views and bespoke wildlife encounters. A summer Christmas at the edge of the earth, kangaroos included!
Nihi Sumba | Sumba, Indonesia
Wild horses galloping on empty beaches and private surf breaks on a remote Indonesian island. Sumbanese culture, jungle spa safaris and a holiday that looks nothing like the one back home.
In case you want a summary without reading the whole thing:
A Warm-Weather Christmas: Best for families and couples who want sun without losing the holiday spirit.
Dashing Through the Snow: Best for active families who want Christmas to look like Christmas.
The Big Family Holiday: Best for multigenerational groups of 8 or more.
A Cozy Christmas: Best for couples and families who want quiet over spectacle.
Disappear for the Holidays: Best for travelers who want somewhere almost nobody has been.
Midnight, Somewhere Glamorous: Best for couples and friend groups who want the New Year's party.
Christmas Market Magic: Best for couples and culture lovers.
Big City Lights: Best for shorter getaways and walkable holiday magic.
An Island All Your Own: Best for milestone celebrations and total privacy.
Christmas on the Water: Best for seeing several places without repacking.
Everything Included: Best for families who want zero logistics.
Skip Christmas as You Know It: Best for repeat travelers ready for something new.
Why Book Your Holiday Trip With Us?
A little inside scoop: we work directly with every property on this list, which means we can often access villas and suites before they hit open inventory, plus perks like upgrades, resort credits and daily breakfast you won't get booking on your own. Over the holidays, when everything is in demand, those relationships make a real difference.
Holiday Travel FAQ
When should I book holiday travel?
As early as possible. The best villas, suites and ski-in/ski-out rooms for Christmas and New Year's often book a year in advance, and by early fall, inventory is already tightening.
Do hotels have minimum stays over the holidays?
Most luxury properties do. 5- to 7-night minimums are common over Christmas and New Year's, and some villas and private islands require even longer. We'll tell you exactly what each property requires before you commit.
Can I still travel over the holidays if I can't take the whole week off?
Absolutely. A Big City Christmas works beautifully as a long weekend, and since most European Christmas markets run from late November through early January, you can see them well before or after the holiday itself.
Remember, you don't need to know where you want to go this year. You only need to know how you want the holidays to feel. Tell me that, and I'll take it from there.
Addie Bell Zackon is the Founder and CEO of Jetset & Travel, a luxury travel advisory based in Park City, Utah.