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Winter's long weekends are the perfect time to get out of town. Whether the post-holiday gloom is starting to grate on you, or you’re just itching to get out of town, you can put serious distance between yourself and real life in just three days. Pack up your skis or fill a duffle with the coziest outfits you’ve been meaning to wear, and choose one of these 11 luxurious long weekend ideas:
Montauk, New York
We’re proponents of venturing to the Hamptons in the winter, when the summer crowds have dispersed but the wineries are still open. After all, oysters are at their best in the colder months, so why not head down to Montauk to enjoy your seafood al fresco with a blanket and heat lamp? Stay at Gurney’s Montauk Resort, open year-round, and set right on the beach. You can dine at Scarpetta Beach or their brand new Bungalows by the Sea, and enjoy a cocktail at The Firepit, Gurney’s outdoor lounge overlooking the ocean.
The music city—or the land of hot chicken, if that’s how you prefer to think of it—makes for a perfect three-day trip, because it’s enough time to really get the flavor of Nashville. From noshing on barbecue smoked by the most revered pitmasters to hot chicken at Hattie B’s, come hungry for this quick trip. Stay at The Joseph, a Luxury Collection Hotel, which just opened in August 2020 and features exceptional design and a stunning collection of contemporary art. When you’re ready to take a barbecue break, The Joseph’s on-site Italian restaurant Yolan is “refined, welcoming, [and] carefully curated,” helmed by James Beard Award-winning chef Tony Mantuano.
There is no destination more delightful than wine country in the winter. With temperatures in the 60s, it’s leather-jacket-great-boots season in Napa Valley, which is why retreating to Calistoga for wine tasting at Tank Garage Winery and Castello di Amorosa could not be more romantic—or relaxing. Stay at Calistoga’s stunning Solage, Auberge Resorts Collection, an American Express Fine Hotels & Resorts property, which feels completely secluded but is in fact just a short walk from downtown Calistoga. The hotel boasts an outdoor pool and beach cabanas dreams are made of, and for a romantic getaway, we’d recommend booking the Silverado Suite with a fireplace and an outdoor hot tub.
The Berkshires, Massachusetts
The Berkshires autumnal colors capture the hearts of folks in driving distance of New England looking for a country respite. But the colder weather brings snow-trimmed scenery and irresistible fireplaces. For a three-day wellness vacation, retreat to Miraval Berkshires Resort & Spa, an American Express Fine Hotels & Resorts property, with a 28,000-square-foot Life in Balance Spa where you can align your chakras and partake in guided meditations, and outdoor adventure experiences like snowshoeing and cross-country skiing.
Scottsdale is on the rise as a chic weekend escape or even a relaxed bachelorette weekend. The desert oasis makes for a perfect spot to unwind by the pool, and the culinary scene has exploded with more than 800 restaurants. Dine at The House Brasserie for French fare or The Mission for Latin American-inspired cuisine. The luxury hotels alone are worth the trip, so stay at the Andaz Scottsdale Resort & Bungalows or Sanctuary Camelback Mountain Resort & Spa, both American Express Fine Hotels & Resorts properties. For a more eclectic, midcentury modern vibe, check out Hotel Valley Ho, and if you can get off work a day early, head to Scottsdale on Thursday to make it in time for the ArtWalk on Thursday nights.
Brooklyn, New York
Unwind with a winter Brooklyn staycation at The Hoxton, Williamsburg. The Hoxton is an Instagrammer’s paradise. Every inch of these boutique hotels is meticulously designed, and the greenery, accent walls, and vintage accessories will leave you wanting to go home and redecorate. If you live on the Upper West Side or in Queens, venture to Williamsburg for a long weekend, where you can stay in the water-facing property and dine at al fresco-chic Aurora or Lillia, a Williamsburg fine dining classic.
Mount Hood, Oregon
Ski the Pacific Northwest at Timberline on Mount Hood, which is actually one of the few U.S. mountains that you can ski year around. Mount Hood, the tallest mountain in Oregon, has more than 11,000 feet of elevation, and Timberline’s highest trail is 8,540 feet up. Stay at Timberline Lodge, which has been a Mount Hood staple since the 1930s. They’ve got luxury condos, chalets that can sleep your whole family, and saunas and hot tubs to rest your muscles après ski.
Explore the Southwest by taking a road trip to the Casper and Laramie area—known for their incredible mountains. Stay at Vee Bar Guest Ranch, a luxe dude ranch that will give you a real taste of what Western hospitality is all about. Built in the 1800s, the property radiates charm from times past, and if you stay in their Riverside Suites, you’ll wake up right along the Little Laramie River. You can ski the nearby Snowy Mountain Range, or spend the day sampling locally made spirits at Backwards Distillery Company.
A luxe retreat in Vail is perfect for those looking to spend their time on a ski mountain, or for those who’d prefer to partake in après-ski without the ski. For next-level lodging, stay at Four Seasons Resort and Residences Vail, an American Express Fine Hotels & Resorts property, where you’ll love the fireside cocktails at The Remedy Bar. Or, book Charter Penthouse for an “European-inspired” ski chalet experience that comes complete with great service, a fireplace, and access to a sauna, hot tub, and multiple pools on-site.
Newport, Rhode Island
While visiting Newport, tour The Breakers, one of the famed Newport mansions where the Vanderbilt's retreated each summer. The mansion is open in the winter months, which is a calm and distinctly picturesque time to explore the mansions along the Cliff Walk. Beyond the mansions, there’s still plenty to do between antiquing at Newport Marketplace and Antiques and feasting on local New England eats. For a five-star historic New England hotel experience, stay at The Chanler at Cliff Walk, which has waterfront views and one of the coziest lobby fireplaces in Newport. Alternately, reserve a suite at Castle Hill Inn, an American Express Fine Hotel & Resorts property set on a private beach that boasts a beautiful spa where you’ll enjoy therapeutic saltwater soaks in the winter. Tack on an extra night to your Newport vacation and take the scenic route over to Westerly, Rhode Island, where you’ll find the iconic Ocean House, nestled in the village of Watch Hill. A triple five-star property (five-star dining, hotel, and spa), adding a night at Ocean House will fully rejuvenate you before heading back to real life.
A thoroughly non-ski weekend in Burlington could be just what you need to break up the monotony of winter. The farm-to-table dining options and Vermont-brewed beer are enough to keep you plenty busy for a few days. Stay at boutique hotel Made Inn Vermont, which describes itself as an “1881 Hip Inn.” They have only four eclectic and curated rooms, and offer romance packages including outdoor hot tub soaks and candle-lit massages with The Shaman’s Touch. Make sure to check out Mad River Distillers and stop in at Leunig’s Bistro while strolling along Church Street for a rustic French meal.