The holidays have a way of arriving faster than expected. Suddenly, the season is approaching and the trip everyone intended to plan months ago remains little more than an idea. Yet a late start does not necessarily mean settling for less. With flexibility, thoughtful guidance and a willingness to consider something unexpected, there are still extraordinary journeys to be found. We reached out to some of our favorite local luxury travel experts for their recommendations on what can—and should—be booked now, along with the insider experiences and thoughtful details that can transform a holiday getaway into something truly unforgettable.
Magical Winter Escapes
Lapland, Finland
For families seeking the full magic of the season, Terry Bahari, founder of TerryB Luxury Travel, recommends Finnish Lapland, where snow-covered forests, reindeer and long winter nights enchant adults as much as children. “Lapland is the ultimate winter wonderland experience,” she says. “It offers a magical mix of festive activities, Indigenous Sámi culture and snow-filled adventures.” Rovaniemi, the capital of Finnish Lapland, sits on the Arctic Circle, surrounded by wilderness lodges, glass-roofed cabins and opportunities for husky sledding, reindeer rides and Northern Lights excursions. At nearby Santa Claus Village, families can meet Santa, visit his official post office and cross the Arctic Circle. Bahari can make the magic begin at home by arranging a surprise visit from one of Santa’s elves, who arrives with a personal invitation to Lapland and a video message from Santa Claus. visitrovaniemi.fi; santaclausvillage.info
Edinburgh and the Scottish Highlands
Gleneagles and Gleneagles Townhouse
Rather than choosing between city and countryside, Jessica Bazan Schwartz, an advisor at Brentwood-based SS Gold Luxury Travel, recommends experiencing both. Begin at Gleneagles Townhouse, a 33-room hotel and private members’ club housed within a restored former bank on St. Andrew Square, with The Spence restaurant in its soaring banking hall and Lamplighters rooftop bar overlooking Edinburgh.“I love a city-to-countryside arc, and an Edinburgh-to-the-Highlands route is one of my absolute favorites,” Schwartz says. “A whisky nightcap at Lamplighters, cozied up in your best knits after a day exploring museums and shops, is true bliss.” From Edinburgh, continue to Gleneagles, set across 850 acres of Scottish countryside, for falconry, clay shooting, horseback riding and other outdoor pursuits. “You bring the coziness to another level with a nightcap by the fire after a day of clay pigeon shooting and falconry with the kids,” Schwartz says. gleneagles.com
Ski, Elevated
Montage Big Sky
Big Sky, Montana
Set beneath Montana’s Spanish Peaks, Montage Big Sky delivers space, service and true slopeside ease, with ski-in, ski-out access and expansive residences and Mountain Homes ideal for multigenerational groups. “The residences combine ski-in, ski-out convenience, incredibly generous space and five-star hotel service,” Schwartz says. “In my opinion, there is hardly another luxury private residence that beats this one in the U.S. ski market.” A ski valet simplifies mornings, while a bowling alley, game room, indoor pool and fireside s’mores entertain families after the lifts close. The 11,000-square-foot Spa Montage offers a restorative end to a day on the slopes. montage.com
St. Moritz to Zermatt by Glacier Express
Badrutt’s Palace and CERVO Mountain Resort
For a quintessential Swiss winter journey, Schwartz pairs the old-world glamour of St. Moritz’s Badrutt’s Palace—known for its storied service, elegant Grand Hall, private ice rink and La Coupole–Matsuhisa restaurant—with the relaxed mountain charm of Zermatt. Connecting the two is the Glacier Express, an approximately eight-hour panoramic journey across 291 bridges and through 91 tunnels, with a multicourse meal served at each guest’s seat in Excellence Class. “I truly believe these two fairy-tale towns were meant to be paired,” Schwartz says. “One offers peak glamour and the other more Alpine charm, while the Glacier Express makes the journey part of the experience.” The trip concludes beneath the Matterhorn at CERVO Mountain Resort, where seven design-forward lodges, lively après-ski and a Japanese-inspired onsen provide a contemporary finale. badruttspalace.com; glacierexpress.ch; cervo.swiss/en
Warm-Weather Wellness
Hacienda AltaGracia, Auberge Resorts Collection
Pérez Zeledón, Costa Rica
Bahari recommends Hacienda AltaGracia for a restorative escape in the foothills of Costa Rica’s Talamanca Mountains. Set across 180 acres of tropical forest, coffee fields and organic gardens, its 50 freestanding casitas overlook the surrounding landscape. At Casa de Agua, treatments, movement classes and thermal experiences are complemented by forest bathing, guided hikes and a riverside ritual culminating in a fire-heated herbal bath. “Hacienda AltaGracia offers a beautiful combination of wellness and adventure,” Bahari says. Guests can also add horseback riding, waterfall excursions and other active pursuits, while complimentary scheduled charter flights from San José International Airport make the remote retreat surprisingly accessible. aubergeresorts.com
Chilean Patagonia
Rio Palena Lodge and Awasi Patagonia
December marks the beginning of prime season in Chilean Patagonia, offering a warm-weather escape defined by wilderness and adventure rather than days beside a pool. “I can hardly think of a place better suited to adventure,” Schwartz says. “Think surreal landscapes, horseback riding with real gauchos and some of the world’s best fly-fishing.” She pairs the intimate Rio Palena Lodge in the remote Aysén region—where days include guided fly-fishing, rafting and private cookouts beneath the stars—with Awasi Patagonia near Torres del Paine. There, every villa receives its own guide and four-wheel-drive vehicle for personalized excursions including puma tracking, hiking and estancia visits. “When you are somewhere this remote, my fear is always: Will the food be good?” Schwartz says. “Fear not here.” elevenexperience.com/rio-palena-lodge; awasi.com/Patagonia
Classic California Getaways
Rosewood Miramar Beach
Montecito, California
Rosewood Miramar Beach brings the holidays to the California coast, transforming its oceanfront Montecito estate with twinkling lights, beautifully decorated trees and festive displays. Seasonal programming ranges from live artists and children’s workshops to celebratory dining, while signature events include Merry Miramar, Christmas Day festivities and Le Bal Cristal, an elegant New Year’s Eve gala. “Nowhere in California beats Rosewood Miramar’s beach setup,” says Emilie of SS Gold Luxury Travel. “After a day at the beach, my perfect afternoon starts with a sunset spritz at the oceanfront bar, rolls into an incredible dinner at Caruso’s and ends with a nightcap at the Manor Bar.” It is a distinctly California holiday escape—oceanfront, glamorous and just a scenic drive from Los Angeles. rosewoodhotels.com/en/miramar-beach-montecito
San Ysidro Ranch
Montecito, California
San Ysidro Ranch becomes especially enchanting during the holidays, when colorful twinkle lights illuminate the grounds and the Speakeasy ceiling is elaborately decorated. Christmas carolers, seasonal menus and celebratory cocktails add to the atmosphere, while guests can retreat to one of 38 vine-covered cottages tucked among the gardens and oak-shaded paths. “San Ysidro Ranch is my definition of a cozy California escape—there’s nothing like a private hot tub and heated outdoor floors to make a chilly evening feel indulgent,” says Emilie of SS Gold Luxury Travel. “I always steer clients toward a fireside dinner at The Stonehouse; it’s the kind of intimate, tucked-away experience you remember long after you’ve left.” The season culminates with a special New Year’s Eve dinner and celebration in the Speakeasy. sanysidroranch.com
Private-Island Escapes
The Brando
Tetiaroa, French Polynesia
Thirty miles north of Tahiti, Tetiaroa is a pristine coral atoll where white-sand beaches and turquoise lagoons meet Polynesian heritage and conservation. Once Marlon Brando’s private sanctuary, the island is now home to The Brando, an intimate resort of secluded villas. “The Brando offers an incredible natural setting and the feeling of being completely removed,” Bahari says. Guests arrive aboard a 20-minute flight from a private lounge in Papeete, then spend their days snorkeling, paddleboarding, exploring with naturalist guides or retreating to a private villa and pool. Through its work with the Tetiaroa Society and the Brando Family Trust, the resort also helps protect the atoll’s environmental and cultural legacy. thebrando.com
Necker Island
British Virgin Islands
Sir Richard Branson’s private island in the British Virgin Islands is known for exclusive buyouts, but select Individual Stay dates allow guests to reserve a room, suite or several rooms within a private Balinese-style house. “You really can stay on one of the Caribbean’s most exclusive private islands without hiring it exclusively,” Bahari says. Dining, drinks, activities and water sports remain included, while the island is shared with a limited number of fellow travelers. The remaining 2026 dates encompass Thanksgiving, November 18–29, and Christmas, December 20–27. virginlimitededition.com/en/necker-island
The Experts
Terry Bahri
TerryB Luxury Travel
310-890-7707
terrybluxurytravel.com
Jessica Bazan Schwartz
SS Gold Luxury Travel
858-551-3022
ssgoldtravel.com