7 Best Winter Vacation Spots

And it’s easy to see why: Berkson has a very finely honed radar when it comes to travel trends, coupled with a penchant for high-end and forward-looking hotels. It’s why I (correctly) assumed that Berkson would be the perfect candidate to select the seven best destinations to travel to this winter.

Below, his recommendations for the best winter vacation spots, of either the domestic or international variety.

Santa Barbara

Santa Barbara is the pride of California’s Central Coast. Only two hours north of Los Angeles, its main thoroughfare State Street is full of chic boutiques, restaurants and bars. While wintertime might not be optimal beach weather, the Pacific is still pretty to look at. That said, if you don’t care about seeing the sea, the 45-minute-away Santa Ynez Valley is chock full of wineries. 

Where to Stay: El Encanto, a Belmond Hotel is a charming stay, with a legacy of hosting some of Hollywood’s biggest names since its opening back in the day. California bungalows span a beautiful hillside, with many overlooking the Pacific Ocean and Santa Barbara (it’s a ten-minute drive to both). As another option for lodging, one of boutique hospitality’s most up-and-coming brands is opening here in January 2023 in Downtown — the 45-room Drift Santa Barbara.

What to Do: It might be too cold to go to the beach (think low 60s during the day), but that doesn’t stop it from being beautiful — walk down State Street until you reach the beach. If you love wine tasting, Santa Ynez Valley is a short drive away. With its endless wineries and vintners:, Sunstone Winery plus Brave & Maiden Estate are great places to start (Auberge Resorts’ new Inn at Mattei’s Tavern, in the adorable town of Los Olivos, is set to open in February). But, one of my favorite parts of Santa Ynez Valley is its most unassuming feature: a town named Solvang, which looks like a little Danish hamlet due to a medley of immigrants hailing from Denmark that settled there back in the early 1900s — expect Danish bakeries, wooden windmills, and a museum dedicated to “The Little Mermaid” and illustrious Dane, Hans Christian Anderson.

Where to Eat: Central Coast cuisine fine-dining restaurant Blackbird sits in the Hotel Californian. From its brass fixtures to its black-box-like appearance, it’s designed to be a nod to Alfred Hitchcock’s haunting thriller films.

Torres del Paine, Chile

Patagonia is a dream and a half, with its snow-capped peaks awash with hiking trails, fertile grasslands that dance in the wind and paradisal lakes. And our winter is their summer — meaning sunnier skies often are the scene in January, February and March. So how do you get to this isolated slice of the world? Fly to Santiago, Chile and then catch another flight to Puerto Natales, which upon arrival, segues into a 90-minute drive to Tierra Patagonia Hotel & Spa (more below on this gorgeous resort that should be your base).

Where to Stay: Tierra Patagonia Hotel & Spa’s wood-framed structuring sits shoreside on Lake Sarmiento, with the peaks of Torres del Paine National Park in the distance. With just 39 rooms, it’s a true boutique hotel. Some of my favorite features include the plethora of expansive windows that naturally bring Patagonia into the interior, the Uma Spa’s menu comprising ritual wraps and scrubs, then, sustainability-wise, how the food, furniture, fabrics and construction materials all come from Patagonia.

What to Do: Torres del Paine National Park spans 370,000 acres of undulating terrain — it’s a hiker’s dream. Expect to see a never-ending list of flora & fauna: Eagles, condors, guanaco, nandu and alpacas are all common sights here. Hike the path along the Cornisas for eye-catching views of the national park’s eponymous peaks — or, if more your vibe, horseback ride with local huasos.

Where to Eat & Drink: Well, you’re a bit more on the isolated side of life here — so, with that in mind, the hotel’s restaurant & bar are going to be your best bet: seafood from the Magellan Strait, local-procured lamb and bona fide Pisco Sours fill the menu.

Palm Springs

This oh-so-retro desert town of Palm Springs is a no-brainer in any conversation about the best winter vacation spots. Temperature highs toggle from the low 60s to the low 70s (February is usually warmer than December and January). The city’s primary locus comprises numerous boutiques, restaurants and stores; many done up in the midcentury modern aesthetic for which Palm Springs is most known.

Where to Stay: A two-minute walk to Downtown Palm Springs’ main heartthrob, Casa Cody is a 30-key hotel that opened in the 1920s and once hosted some of Hollywood’s most notorious elite. Here, adobe-style and California Spanish Colonial-style casitas span the premises, many hidden in secret gardens or covered in eye-catching bougainvillea.

Another stay I love is Korakia Pensione, which, architecturally, comprises a repurposed 1924-constructed Moroccan-style villa, a Mediterranean villa and a Spanish adobe house — expect pleasant courtyards here that breathe a sense of calm. 

What to Do: Walk Downtown Palm Springs and do some serious retail therapy — head to Mr. Turk for chic retro menswear, buy plates and coasters with hilarious irreverent quotes imprinted on them (if you get offended easily, maybe skip this one) at Michael Weems Collection, and debate on whether you need a cool new midcentury modern lamp in your house while moseying around furniture store, Pelago. If time with nature is what you’re looking for, take the Palm Springs Aerial Tramway up to the top of the San Jacinto Mountains, which are covered in snow at their summit, and full of hiking trails with sweeping views of Palm Springs and its neighboring towns.

Where to Eat & Drink: Birba is an atmospheric restaurant with an outdoor patio in the center of town. The cauliflower pizza selection here is “above par.” Another spot I love is Boozehounds — weekend brunch on their patio under the sun is pleasant and delicious. 

Bacalar, Mexico

Located off Mexico’s Yucatan Peninsula, the town of Bacalar’s namesake lake is most likely the reason you’ve heard of the area. That said, you also might not have heard of it at all, being that it’s a burgeoning travel destination and not as famous as other idyllic Mexican spots such as Tulum and Cabo. The lake glimmers in varied shades of blue and is a total feast for the eyes. Bacalar’s tropical climate is perfect for vacationers looking to decamp the cold and go somewhere warm.

Where to Stay: Casa Hormiga is an 18-room boutique hotel one block away from the lake. Expect to decompress at this jungle sanctuary from the thrum of city life. To help you detox from stresses back home, the hotel hosts traditional temazcal steam lodges, sound healing sessions and cacao ceremonies.  

What to Do: Swim, sail, kayak and paddle-board Lake Bacalar during the day. Later, get your history fix one hour away at Kohunlich, a remote Mayan ruin that spans 21 acres.

Where to Eat & Drink: Head to town and grab a bite at praised Mexican restaurant, Macario. For some time on the sand, lay on a hammock and sip cocktails at Bacalar’s zingiest beach club, La Playita.  

São Paulo, Brazil

Brazil-bound travelers often overlook South America’s biggest city, São Paulo, for its beachy counterpart, Rio de Janeiro. Skipping it is a disservice — Sao Paulo pulsates with a unique, enlivening energy that affirms its metropolis status, from its attraction-filled parks to vibrant nighttime haunts.

Where to Stay: Spend your nights here at the Rosewood São Paulo. Occupying a former maternity ward in the city’s Bela Vista neighborhood, the hotel is right down the street from Avenida Paulista and its slew of designer stores. The rooftop pool is the lido you need in your life.

What to Do: São Paulo is chock full of attractions. Visit Ibirapuera, one of South America’s largest parks, which houses a greenbelt abundance, as well as the impressive São Paulo Modern Art Museum and Afro Brasil Museum. 

Where to Eat & Drink: Drink and dine at the debonair Baretto at Fasano Sao Paulo, a glamourous 1950s-style supper club with live music. Expect superb cocktails and ambrosial plates, all while watching a bossa nova or jazz performance up close. 

Park City, Utah

If you’re looking for a winter vacation spot that really screams winter, Park City, Utah, is one of the USA’s most charming ski towns, and it’s exceedingly convenient — just a 35-minute from Salt Lake City’s major airport. The Canyons, Deer Valley and Park City Mountain Resort are nearby ski resorts that are replete with shred-worthy slopes.

Where to Stay: Stay at the Washington School House Hotel, a 12-room boutique hotel just off Park City’s Main Street and all the stores, restaurants and bars that come with it. Set in an erstwhile 19th-century school, expect French furnishings, crystal chandeliers and white marble bathrooms. The all-season outdoor heated pool is a must on a cold winter day.

What to Do: Ski, snowboard, repeat! Some of the world’s best skiing is here. If you want to ski and snowboard, head to The Canyons and Park City Mountain Resort (there’s a lift right in town, minutes away from the Washington School House Hotel). If you want to be with fellow skiers — and only skiers — the no-snowboarders-allowed, luxe Deer Valley ski resort befits your desired vacation vibes. If you need a day off from powdered slopes, Park City’s Main Street is the perfect place for a shop & walk.

Where to Eat & Drink: Have a non-bougie après ski moment at Davanzas down the street, which, in my opinion, has some of the best pizza and tacos in the city. The Park City staple’s décor is “bona fide ski bum” — walls are stocked with endless beer cans from around the world, a Farrah Fawcett photo from the 1970s hangs on the wall, and ski- and snowboard-oriented images freckle the space.

Madrid, Spain

Madrid is one of Europe’s most dynamic cities. The metropolis stuns all visitors through its exceptional selection of museums, streets sporting warm-colored buildings and authentic tapas bars.

Where to Stay: Located in the city’s Salamanca neighborhood, Tótem Madrid is modish but not in a forceful way. Part of Small Luxury Hotels of the World, the lobby of this intimate 64-key hotel boasts marble floors, brass accents and a meticulously restored staircase that dates back to the 19th century.

What to Do: Hit two of Spain’s most iconic museums: El Prado, which houses art from El Greco, Goya, and Velázquez, and the Reina Sofia, where many of Picasso’s works are on display, including the world-famous Guernica. Spend some time soaking up old Spain at Plaza Mayor, and then after that, amble around the city’s El Retiro Park.

Where to Eat & Drink: Eat and Drink at Jeronimo at The Edition: Madrid. Culinary efforts here are led by hyper-lauded chefs Diego Muñoz and Enrique Olivera (if you ever head to Mexico City, his restaurant Pujol is fantastic). Jeronimo serves Mexican food prepared with Spanish products. That said, should you be looking for something more authentic, indulge in tapas — a must if you’re visiting Spain — at 127-year-old Madrid institution, Bodega de La Ardosa Order the Tortilla Española when here.

Singapore

Head to Singapore in Southeast Asia for a visit you won’t forget. It hosts one of the world’s most design-centric airports (it would be a disservice if I didn’t talk about the airport — seriously, there’s an inimitable gargantuan waterfall flowing down from its ultra-high-ceilinged atrium roof), a famous botanical garden that’s a lens into the future of horticulture and a melting pot comprising different cultures, mainly citizens of Chinese, Malay, Indian and Eurasian descent.

Where to Stay: Over 100 years old, Raffles Singapore is the city-state’s luxe grand dame stay, displaying a recently-renovated ritzy colonial-style building and manicured gardens that woos guests left and right. Its rich pedigree has seen it host some of the world’s most illustrious figures: Charlie Chaplin and Queen Elizabeth II are two of many.

What to Do: Gardens by the Bay is the archetype of what constitutes a garden of the future. Suspended walkways entwine through clusters of lush foliage and solar-powered “supertrees” stemmed in steel. Those looking to immerse themselves in local culture should visit Little India: Tour local Hindu temples, pop into Indian art galleries while walking down the colorful marigold-abundant thoroughfare Serangoon Road, and learn about Singapore’s South Asian community at the Indian Heritage Center.

Where to Eat & Drink: Grab a drink at Lantern House, which boasts sweeping views of the city’s most iconic tower, Marina Bay Sands (you’ve definitely seen the Marina Bay Sands — it’s the one with that “Insta-worthy” rooftop infinity pool looking out at the skyline). Food-wise, Singapore’s hallmark Hawker cuisine is a must-try — start with a chicken satay at buzzy nighttime eatery and ultra-authentic Singapore staple, La Pa Sat.