There is something particularly memorable about spending the holidays away from home. Christmas morning might begin beneath palm trees in Hawaii, with pastries overlooking the rooftops of Vienna, or in a Manhattan suite before heading out to see Fifth Avenue dressed for the season.
For 2026, we are looking at five destinations that each offer a very different way to celebrate, from Christmas markets in Vienna to a barefoot New Year’s Eve in Hawaii.
Vienna, Austria
If there is a city made for December, it might be Vienna.
By mid-November, the Austrian capital has fully embraced the season. Lights stretch across its grand avenues, shop windows are dressed for Christmas, and historic squares fill with wooden stalls selling ornaments, pastries, roasted almonds and steaming mugs of punch
Start at the Viennese Christmas Market at Rathausplatz, the city’s largest, which runs from November 13 through December 26 in 2026. Then seek out some of the smaller markets. Schönbrunn Palace hosts its Christmas market through January 6, while the Old Viennese Christmas Market at Freyung has a more intimate, traditional atmosphere.
The city rewards slowing down. Spend an afternoon inside the Kunsthistorisches Museum, arrange a private tour of Schönbrunn Palace, attend a performance at the Vienna State Opera or simply settle into one of Vienna’s grand cafés over coffee and cake.
Where to stay: Rosewood Vienna. Set on Petersplatz in Vienna’s historic center, Rosewood Vienna is exceptionally well positioned for a festive stay. Many of the city’s Christmas markets, shops and cultural landmarks are within easy reach, while the hotel itself feels more residential than grand-hotel formal.
For Christmas Eve, the hotel traditionally creates a special festive dinner, while its rooftop Neue Hoheit restaurant serves contemporary Austrian cuisine overlooking the city.
What to do: Browse the Christmas markets after dark, ice skate at Rathausplatz, attend a classical concert, visit Schönbrunn Palace and leave an afternoon free for Vienna’s café culture
Where to eat: For a celebratory dinner, book Steirereck, one of Vienna’s best-known destinations for contemporary Austrian cuisine. For something with more old-Vienna atmosphere, stop at Zum Schwarzen Kameel, a Viennese institution dating to the 17th century. At the hotel, Neue Hoheit is particularly appealing for a dinner overlooking the city’s rooftops.
Make it a New Year’s trip: Vienna is just as compelling after Christmas. The city traditionally celebrates New Year’s Eve with festivities throughout the historic center, while Rosewood has previously paired its New Year’s Eve gala dinner with a midnight celebration from its rooftop.
Best for: Couples, families with older children, art and music lovers, and travelers who want the holidays to look exactly as they imagined them.
London, England
London manages to make Christmas feel both nostalgic and completely over the top
Regent Street and Bond Street glow after dark. Department stores compete over elaborate windows. Hotels turn afternoon tea into an event. Pubs light their fireplaces. And because this is London, you can spend one afternoon immersed in holiday festivities and the next at the British Museum or seeing a West End production.
In 2026, seasonal events include The Nutcracker ballet, Hogwarts in the Snow studio tour, Christmas markets, and holiday light displays across the city. Hanukkah falls December 4 through 12, giving December travelers another reason to seek out the city’s seasonal celebrations.
Where to stay: Claridge’s. Few hotels are as closely associated with Christmas in London as Claridge’s. The Mayfair hotel has made its annual Christmas tree something of a London event, inviting a different designer or fashion house to reinterpret it each year.
Staying here also puts you in the middle of the action. Bond Street, Regent Street and some of London’s best shopping are close by, making it easy to head out for the day and retreat to Claridge’s when you have had enough of the crowds.
Afternoon tea in The Foyer & Reading Room is a tradition worth making time for, particularly during the festive season.
What to do: See the Christmas lights after dark, shop Mayfair and Bond Street, book a West End show, visit the Christmas markets and make time for a festive afternoon tea. Families can add The Nutcracker or Hogwarts in the Snow.
Where to eat: London is worth planning a trip around for the restaurants alone. For one memorable evening, reserve Gymkhana for its refined take on Indian cuisine. For a classic Mayfair dinner, The Connaught Grill is only a short distance from Claridge’s. And at least once, have afternoon tea without leaving the hotel.
Stay through New Year’s: London’s fireworks over the Thames are the headline event on December 31. River cruises and restaurants with views become especially sought after, so this is one night we would plan well in advance.
Best for: Families, first-time visitors, theater lovers, shoppers and anyone who likes having an almost endless list of things to do.
Costa Rica
Trying to escape the cold this year?
At Hacienda AltaGracia in southern Costa Rica, December mornings begin with warm breezes and birdsong rather than traffic. The 50-casita resort sits on 180 acres in the foothills of the Talamanca Mountains, surrounded by tropical forest, gardens and coffee plantations.
This is the destination on our list for travelers who want the holidays to feel like a genuine reset.
Where to stay: Hacienda AltaGracia, Auberge Collection. AltaGracia is less about checking sights off a list and more about immersing yourself in where you are. Days might involve horseback riding through the countryside, hiking to waterfalls, visiting coffee plantations or spending several hours at The Well, the resort’s expansive wellness center.
December also falls during the beginning of Costa Rica’s dry season, making the holidays an appealing time to explore the country.
There is a wonderful sense of place here for families as well. Instead of building the holiday around elaborate decorations and shopping, you can make it about time together outdoors.
What to do: Ride horses through the mountains, visit a local coffee farm, hike to waterfalls, spend a morning bird-watching or devote an afternoon to The Well. For serious birders, nearby Los Quetzales National Park is one of the places to look for Costa Rica’s resplendent quetzal.
Where to eat: This is one destination where we would largely stay on property. AltaGracia’s setting lends itself to lingering meals and locally sourced ingredients, and the resort’s connection to the surrounding agricultural community is part of the experience. Its own coffee cultivation is particularly fitting in Costa Rica’s Brunca coffee-growing region.
Make it festive: Christmas in Costa Rica comes with its own traditions, from tamales and family gatherings to elaborate nativity scenes. Rather than trying to recreate a snowy Christmas somewhere tropical, lean into the destination. Let the holiday feel Costa Rican.
Best for: Families, wellness travelers, couples, active travelers and anyone who reaches December ready to relax.
New York City
There are few places where being a tourist is more fun than New York in December.
Start early with a walk through Central Park. See the Rockefeller Center Christmas tree, admire the Fifth Avenue windows and head to a Broadway matinee. Ice skate beneath the skyline, spend a few hours at the Museum of Modern Art and finish the evening over dinner and cocktails.
The key is resisting the urge to schedule every minute.
New York during the holidays is crowded, and the pleasure comes from having the right reservations in place while leaving enough room to wander.
The city is also one of the strongest destinations on this list for travelers celebrating Hanukkah. From December 4 through 12, 2026, the city’s largest menorahs are scheduled to be lit nightly at Grand Army Plaza in Manhattan and Brooklyn, accompanied by live music and traditional foods.
Where to stay: Aman New York. Aman New York provides an almost surreal counterpoint to the city outside. Located in the Crown Building on Fifth Avenue, the 83-suite hotel feels remarkably removed from Midtown despite being in the center of it
That contrast is particularly appealing in December. Spend the day among the lights, shoppers and holiday crowds, then retreat to Aman’s 25,000-square-foot spa. River Oaks Travel clients receive preferred amenities at the hotel.
For the 2026 festive season, Aman is planning seasonal dining at Arva and Akari, wellness programming, and a New Year’s Eve gala followed by a countdown at its Jazz Club.
What to do: See the Rockefeller Center tree, visit the holiday windows along Fifth Avenue, skate at Rockefeller Center or Central Park, see a Broadway show, visit MoMA and experience one of the city’s public menorah lightings during Hanukkah.
Where to eat: For a special lunch or dinner near MoMA, The Modern is an easy addition to a museum day. Le Rock at Rockefeller Center puts you directly in the middle of the holiday atmosphere. And for at least one evening, stay in and dine at Aman’s Arva or Japanese restaurant Akari.
Stay for New Year’s: Times Square may be the city’s most famous celebration, but it is hardly the only way to ring in the year. A beautifully planned dinner, live music and a midnight toast can make for a far more relaxed December 31. Aman itself is planning a gala dinner and Jazz Club countdown for 2026.
Best for: Couples, food lovers, shoppers and travelers looking for a festive long weekend rather than a two-week vacation.
Hawaii
There is something particularly appealing about leaving winter behind and spending the holidays in Hawaii. December days can revolve around the ocean, long lunches, golf and time outdoors, with just enough festive programming to make it still feel like the holidays.
Where to stay: Mauna Lani, Auberge Collection. Set along the Kohala Coast, Mauna Lani is a Virtuoso property that works especially well for families and multigenerational groups. The resort combines a beautiful beachfront setting with golf, tennis, water activities, cultural programming, a kids’ club and plenty of space to slow down.
It is also a destination where you can comfortably stay for a week without feeling the need to constantly leave the resort. Spend mornings snorkeling or paddling along the coast, take a Hawaiian cultural class, book a round of golf or simply claim a spot by the water.
For travelers who do want to explore, Hawaii Island offers far more than beaches. A private guide can take you through the dramatically different landscapes of Hawaii Volcanoes National Park, while an evening excursion toward Mauna Kea offers some of the world’s most remarkable stargazing.
What to do: Snorkel along the Kohala Coast, explore Hawaii Volcanoes National Park with a private guide, go stargazing, play a round of golf, spend time learning about Hawaiian culture and leave at least one day completely unscheduled.
Where to eat: CanoeHouse is the resort’s signature oceanfront restaurant and the natural choice for a special dinner, with Japanese-influenced dishes built around ingredients from Hawaii. For a more casual meal, HaLani offers relaxed resort dining throughout the day. Off property, Merriman’s in Waimea is a longtime favorite for Hawaii Regional Cuisine and locally sourced ingredients.
Make it festive: Rather than trying to recreate a traditional mainland Christmas, embrace being in Hawaii. Spend Christmas Day by the ocean, plan a special dinner that evening and let the resort’s festive programming add just enough holiday tradition. For New Year’s, the Kohala Coast is an ideal place to end the year with dinner, Champagne and the Pacific as the backdrop.
Best for: Families, multigenerational groups, golfers, couples and travelers who want the holidays to feel like a true vacation.
Why Its Best to Plan Early
Holiday travel is one of those occasions when planning early matters. The best holiday trip is rarely the one pieced together in December.
The stretch between Christmas and New Year’s is one of the busiest travel periods of the year, and the longer you wait to plan the fewer options you’ll have. Connecting rooms, multi-bedroom suites and villas become very limited. The best private guides and restaurant reservations go quickly. Resorts may have minimum-stay requirements, and Christmas and New Year’s Eve often bring special dining programs that require advance reservations.
Planning now gives you something particularly valuable: choice.
Let Someone Else Handle the Holidays
The holidays are supposed to be the time of year when you reconnect with the people you care about. They should not begin with six months of researching hotels, comparing room categories and trying to figure out which restaurants are actually open on Christmas Eve.
At River Oaks Travel, we plan the entire trip, from choosing the right destination and hotel to arranging flights, private guides, transfers, dining and experiences.
Because our advisors work as a team, every client benefits from the collective knowledge and experience of our entire team, not just one advisor.
So, when December arrives, the reservations are made, the details are handled and there is nothing left to do but go.
Considering traveling for holidays? Now is the time to start planning. Contact River Oaks Travel to get started.
"There’s something so special about experiencing the holidays through another destination’s traditions, food, and celebrations."
Colleen Wolfe, Marketing Director, River Oaks Travel
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