As someone who’s spent the past decade in the Northeast, I know all too well how polarizing winter can be. I have friends who are ski bunnies and relish the snow days, and others who are snowbirds, seeking any excuse to flock south to sunshine and margaritas.
Personally, I fall somewhere in between—I appreciate the seasons as they are a reminder of life’s cyclical rhythm, but also realize how drawn out New England winters are, thus resulting in at least one or two warm weather escapes between January and March.
I took my first of these two weeks ago to the British Virgin Islands. It happened to be snowing the morning I left so arriving at Rosewood Little Dix Bay’s turquoise inlet felt especially soothing. The first thing I did was run out to the beach to feel the sand between my toes, then to the water’s edge in my travel joggers and all, immediately unwinding from the sense of calm the salt air brings with it.
The next few days were spent sipping Painkillers (fun fact: this dark-rum based cocktail was reputedly invented in the BVIs in the 70s at the Soggy Dollar Bar), diving into boulder-lined bays (The Baths National Park is a must-see), dining on simply prepared seafood (Caribbean lobster is an absolute favorite of mine, sorry Mainers) and wondering if the four seasons are really all they’re cracked up to be… kidding, but the tropics certainly felt flawless in the here and now. It was a pretty seamless getaway from Boston (a direct flight to SJR then a Tradewind puddle jumper to Virgin Gorda) which got me thinking about long weekend getaways at this time of year.
Rather than relying on my favorites, I tapped some of my well-seasoned friends in the travel industry for their favorite long-weekend trips during this time of year. From Palm Springs to Jackson Hole, I loved reading about the destinations on their radar this winter; I hope you will too!
Charleston, SC
For design & cuisine, recommended by Brayan Mesa, photographer & social media consultant
“This Southern Charmer delivers on every promise: cobblestone streets lined with pastel-hued mansions, rich history, southern hospitality, and a laid-back beach vibe. Lose yourself in the historic district, peek into hidden courtyards, marvel at architectural gems, and fuel your appetite at one of their renowned restaurants. 167 Raw Oyster Bar is a personal favorite and while they don’t take reservations, you can sign into the queue, walk around the corner to Bar167 and enjoy a “Fire in the Garden” while you await for your table. For an evening on the Charleston Harbor, charter a boat and gather your crew, brews, and cozy blankets to experience the sun dipping below the horizon, painting the sky in fiery hues. To charter a local boat, visit: DiscoverBoating.com.
Wondering where to stay? Conde Nast Traveler wasn't wrong when they named The Pinch one of the "Best New Hotels in the World" in 2023. This chic boutique hotel boasts 25 designer rooms & suites, spa services, and three top-notch dining options all just steps from the vibrant energy of King Street. From bustling restaurants to hidden gardens, Charleston whispers secrets in every breeze. Listen closely, and you'll find your own perfect corner of paradise in this captivating Southern gem.”
Palm Springs, California
For wellness, recommended by Joey Skladany, food & travel writer
“I am a self-hating gay (kidding, kind of), so I went into the LGBTQ+-friendly destination with a bit of skepticism (Fire Island is not my jam), but I was blown away by the art, food, and landscape of Palm Springs. There is so much to do, whether it's relaxing by the pool, hiking the San Jacinto Mountains, or bopping from shop to shop on Palm Canyon Drive. The *only* thing you have to worry about is snagging a table at Rooster and the Pig—arguably one of the best Vietnamese restaurants in the country, but they don't take reservations.”
Rosewood Baha Mar
For a luxury beach getaway, recommended by Kristen Shirley, luxury expert & founder of La Patiala
“This is one of my favorite weekend getaways from New York; it’s a quick three-hour flight to Nassau, but you instantly feel transported to another world. The property is elegant and serene, but it’s part of the larger Baha Mar complex so you can venture out to try more restaurants, while still having the Rosewood to escape to. (Only Rosewood guests can use the amenities of the other resorts, it’s not reciprocal.) My favorite way to spend my time is relaxing on an oceanfront beach chair, spending the day swimming in the warm water and eating tacos on the beach. If you want to explore Nassau, the concierge can book a driver and tour guide for you, so you can see landmarks like the Queen’s Staircase, which dates to the 1700s, the National Art Gallery, and indulge in fresh, local seafood.”
Stowe, Vermont
For skiers & the foodies who love them, recommended by Todd Plummer, travel writer
“Easily reached by car in a few hours from Boston and New York, Stowe wins major points for accessibility. Sure, it’s an East Coast mountain with modest elevation and variable conditions. But between the town and the resort, this charming ski area has evolved into a fabulous destination for skiers and non-skiers alike. I’d go so far as to say it stands up to anything you’d find out West—no flying required.
Yes, the resort is excellent for downhill skiers of all levels. But there are also tons of cross-country ski trails in this area if you’re looking for more gently sloping thrills. But for me, what really sets Stowe apart is the rich F&B scene. Up at the hill, as locals say, it’s all about a boozy aprés-ski at the WhistlePig Pavilion, and then on to Alpine Hall for elevated takes on ski fare—think charcuterie, lobster frites, and rich cassoulet. On the access road, Matterhorn is a favorite for (trust me) sushi. The area also has some well-established foodie favorites such as Hen of the Wood and Plate. Make sure to visit Idletyme Brewing Company and The Alchemist for beers to bring home as souvenirs, and Vermont Artisan Coffee & Tea in neighboring Waterbury on the way back to the highway. The latter, located in a really beautiful converted barn where you can see the beans getting roasted, feels like a great symbol of how this quiet, rural town has reinvented itself for a new generation. It’s also the best cup of coffee in this part of New England.”
Quebec City
For history & culture, recommend by Valérie Vaillancourt, travel, photography & influencer relations
“Now that I’ve moved away, I shamelessly love recommending long weekend trips to my hometown of Québec City. It’s a popular destination year-round, but there’s something magical about strolling the streets of the Old Town while its covered in a blanket of snow. It’s a cliché to locals, but it truly is like a piece of Europe in America – French flair and all! Step into history in Quartier Petit Champlain – be sure to stop by Café La Maison Smith in Place Royal when you’re ready to warm up. Indulge in modern Scandinavian-inspired wellness at Strom Spa in Old Québec—enjoy hot baths, steam and dry saunas, and cold plunges with a breathtaking view of the St. Lawrence River.
Stay at the most photographed hotel in the world at Fairmont Le Château Frontenac (and treat yourself to a cocktail at Bar 1608 while you’re there) or go the maximalist route and call Monsieur Jean - Hôtel Particulier home while you’re in town. Try your hand at ice skating at the ice skating rinks at Place D’Youville or on the Plains of Abraham. Savor traditional Canadian, sugar-shack-inspired cuisine at La Bûche or head underground at Restaurant Tanière3, nestled underneath vaults dating back to 1686.”
Jackson Hole, Wyoming
For luxury & adventure, recommended by Katherine Parker-Magyar, travel writer
“The most beautiful town in the United States — and the best ski town in North America — used to be inaccessible for a long weekend, but now with the plethora of direct flights to the newly-expanded airport, a 3-4 day trip is suddenly possible (and beyond desirable for a mountain getaway). Jackson Hole is a picturesque journey into the wild during all four seasons, from fly fishing and hiking in Grand Teton National Park in the summertime, to autumnal horseback riding, springtime white water rafting, and Nordic and downhill skiing at Jackson Hole Mountain Resort in the winter months. My favorite restaurant in town is the Snake River Grill, while Dornans provides jaw-dropping views of the mountains (and mouthwatering margaritas). If you want to soak in the views in style, book a stay in Amangani. Otherwise, Spring Creek Ranch provides spectacular views of the mountain range (ang glorious horseback riding), and The Lodge at Jackson Hole is ideally situated between the old town square and the ski resort. The mountains are calling, and we should all go!”
Bocas del Toro, Panama
For culture & nature, recommended by Taliya Maya, travel expert & founder of T World Tours
“This archipelago—nestled off the coast of Panama in the Caribbean—is a haven for those who revel in nature's beauty, with its pristine beaches, lush rainforests, and teeming coral reefs. But it's the rich cultural fabric that truly defines Bocas del Toro. Here, the vibrant mix of Panamanian and Afro-Caribbean influences comes alive in the rhythmic music, lively dance scenes, and colorful festivals. For those seeking a stay that captures the essence of the region, La Coralina Island House is an exemplary choice. This boutique accommodation, set on a private island, offers a serene and intimate setting. Its strategic location also offers convenient access to popular activities like snorkeling, surfing, and exploring the lush rainforests. Staying here isn't just about finding a place to sleep; it's about engaging with the heart and soul of Bocas del Toro, making your brief vacation both enriching and memorable."
Miami Beach
For luxury & wellness, recommended by Samantha Leal, lifestyle & travel writer
“Miami isn't just for late nights and revelry (though that's fun, too)—it's also a great place for a solo getaway and/or wellness-focused activities. Home to Carillon Miami Wellness Resort (the largest wellness-focused resort in the East), where you can do things like a hydrotherapy circuit, it's also home to some of the best luxury hotels to relax — the 1 Hotel South Beach, The Miami Beach Edition, and Fontainebleau Miami. There's nothing like indulging in a great meal (there's so many great restaurants in Miami), spending the day by a pool or beach, and enjoying a massage or some other treatment. There's a ton of flights (which makes it easy to get to and out of), and you can really make the city what you want.”
Porto, Portugal
For a farther flung European escape, recommended by Charlie Neville, marketing lead, JayWay Travel
"Porto, a hidden gem on the Iberian Peninsula, is an enchanting and under-explored haven. It's a destination where the charm of old Europe seamlessly blends with a vibrant, contemporary buzz. With most U.S. cities now offering direct flights to its welcoming airport, a quick four-day escape to Porto has never been easier. The city is a trove of experiences, still feeling like a well-kept secret, away from the crush of mass tourism. Here, you can indulge in the rich flavors of Douro and Port wines right at their source. Porto also offers exceptional value for money, especially for those seeking luxury experiences. Both high-end hotels and gourmet restaurants provide opulence at surprisingly affordable rates, making Porto a haven for travelers seeking luxury for less."
Mayakoba, Mexico (Playa del Carmen)
For luxury wellness, recommended by Jennifer Rice, travel & culinary writer, founder of Bitchen newsletter
“I recently visited Rosewood Mayakoba for a long weekend as JetBlue has a 3.5-hour direct flight from RDU to Cancun. The resort is about an hour from the airport and you can get there shortly after noon for a full day of sunshine ahead. When there, the biggest choice is where to eat and drink. I still daydream about huevos divorciados (divorced eggs) at Casa del Lago and the extensive pastry spread; the corn ribs and shrimp tacos at Aqui Me Quedo; and dinner and all the drinks at Zapote. If you're lucky the bartender will invite you to a secret room filled with sotol, tequila, mezcal, and lots of intriguing elixirs where a metal cup is filled with the dealer's choice of liquid.
I spent a lot of time meditating, sleeping (the beds are heavenly), taking baths in the all-glass bath area looking out into plush greenery—and of course, the spa, even without treatment is such a treat and perhaps my favorite spa in the world. I did embark on a shamanic journey in a sweat lodge (and will be essaying about this soon so stay tuned for more as it was a... trip! It's a place I'd recommend going solo for a reset or with a lover for a grand time in and around the spacious suite.”
Anna Maria Island and Bradenton, Florida
For family travel, recommended by Alissa Fitzgerald, writer, recipe developer & chef
“Flying into Sarasota airport is shockingly easy. Winter off season is my favorite time down there and the island is just as beautiful and way less packed than at high season. Good for families, baby-moons or low-key trips. Stay at Seaside at Anna Maria Island Inn for beachfront sunsets and endless toes-in-the-sand walks right outside your patio door. Eat everything at Beach House Restaurant, Tide Tables in Cortez and Anna Maria Oyster Bar for the fresh, locally-caught seafood. The snow crab claws alone are worth a trip. Then head over to the Maritime Museum in Cortez for fish painting and a little history of the last active fishing village on the Florida Gulf. And yes, you paint a fish which becomes a take-home piece of art.”
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