The Perfect Getaway: A long-weekend ski trip in Vail, Colorado
A winter wonderland awaits in Vail, setting the scene for a perfect long-weekend getaway filled with skiing, shopping, hot chocolate, and other wintertime fun.
By Jessica Poitevien | January 2, 2026
With more than 5,300 acres (2,145 hectares) of skiable terrain, dozens of lifts, a lively aprés-ski scene, and even heated sidewalks, it’s no surprise that Vail, Colorado, is considered one of the best ski destinations in the country. Whether you’re a newbie hitting the bunny slopes or an expert in search of black diamonds, Vail caters to skiers of all abilities, with plenty of fun worth discovering off the slopes, too. Here’s the perfect itinerary for a long winter weekend in Vail.
Friday
Morning
Say hello to Vail, and don’t be surprised if this reliably snowy winter destination welcomes you with a fresh coat of powder. Check into Highline Vail - a DoubleTree by Hilton and settle into a mountain lodge-inspired room or one of the spacious loft-style suites, which are perfect for families and friends staying together. It’s easy to recuperate from your travels, with the 24-hour Made Market offering snacks and drinks. Grab a cup of hot cocoa and unwind in the cozy lobby or by the outdoor fire pit.
Afternoon
Once you’ve relaxed and worked up an appetite, enjoy a hearty lunch at Del Toro Mexican Cuisine. You’ll be spoiled for choice with a menu featuring traditional Mexican fare alongside seafood dishes specifically inspired by the country’s Mazatlan region. With a full and happy stomach, it’s time to start exploring. Head to the Colorado Snowsports Museum and Hall of Fame to learn about the fascinating history of skiing and snowboarding in the region, from the most famous winter athletes to ski fashion throughout the decades.
Evening
The iconic Vail Village awaits nearby and should be your next stop. Stroll through the cobblestone streets, popping into the designer boutiques, fine art galleries, and shops filled with locally made crafts, handmade jewelry, and more. The Solaris Ice Rink is also open during this time of year so rent a pair of skates and glide around the ice under the stars and twinkling holiday lights. With plenty of bars and restaurants in Vail Village, enjoy a flavorful meal before retreating to the hotel.
Saturday
Morning
Fuel up for a day on the slopes with breakfast at the hotel’s Westside Cafe, where you’ll find American favorites alongside dishes that put a twist on classic morning foods. From buttermilk pancakes to bison eggs benedict, there’s something to satisfy every palate. Then make your way to the ski lifts on the complimentary shuttle to Vail Village. In need of equipment? Charter Sports has an outpost at Highline Vail with quality rental equipment offered at a discounted rate for hotel guests.
Afternoon
After a full day of skiing, the European-inspired atmosphere of Vail Village is the perfect place to enjoy some après-ski festivities. Pepi’s Bar & Restaurant is a favorite for its sunny patio and traditional Austrian menu, while locals and visitors alike flock to The Red Lion for its live music. Don’t miss out on Colorado’s renowned craft beer at Garfinkel’s or the Vail Brewing Company, but if you prefer a sophisticated wine and cocktails scene, Root & Flower is sure to impress.
Evening
Back at the hotel, let the après-ski fun continue with a round of foosball and cornhole in the game room. Freshen up before dinner at Pivot62, where you’ll be treated to a variety of shareable plates like truffle fries and empanadas. Brick oven pizzas are a specialty of the house and definitely worth ordering. Round out your meal with one of the many creative cocktails like the Oaxaca Caipirinha, made with mezcal and cucumber, or the Silkroad Martini with rose water and saffron.
Sunday
Morning
Get an early start to make the most of your last full day in Vail. You could easily spend another day skiing and snowboarding on the bunny slopes, back bowls, and black diamonds, or try the other wintertime activities in the area. At Vail Nordic Center, a golf course is transformed into miles of trails perfect for mostly flat cross-country skiing, fat tire biking, or snowshoeing. For a truly unique adventure, the concierge at Highline Vail can also recommend a local company for dogsledding tours.
Afternoon
No matter what snow-filled activities you get into, you’ll probably be tuckered out and in need of some serious relaxation. Take a dip in the hotel’s oversized hot tub, float peacefully in the heated outdoor saltwater pool, or gather around the outdoor fireplace with a cocktail in hand. Soothe any sore muscles at the on-site Mountain Revival Spa, with restorative treatments like the deep tissue massage or trigger point therapy. Aromatherapy, hot stones, and hydrating facial masks are also available to enhance your experience.
Evening
Complete your Vail experience with a taste of the local nightlife starting with a delicious dinner. You can’t go wrong with a stop at Sweet Basil, known for its creative takes on American cuisine. Or snag a table at Chasing Rabbits, which is equal parts bar, restaurant, and entertainment venue. There, dinner easily bleeds into a nightcap at the speakeasy-style bar or hours of dancing to spinning DJs. For the best of both live music and DJs, head to Bridge Street Bar for late-night fun.
Monday
Morning
Whether you first grab a quick breakfast at Made Market or sit down for a full meal at Westside Cafe, there’s still plenty of time for enjoying Vail’s wintertime offerings. Explore Lionshead Village, a Bavarian-inspired community with charming shops and an ice-skating rink. From there, hop on the Eagle Bahn Gondola (#19), or head to Vail Village for a ride on Gondola One. Both options will send you soaring high above the trees as you soak in picturesque mountain views along the way.
Afternoon
You’ve seen Vail’s natural beauty from above, now explore it at eye level with a visit to the Betty Ford Alpine Gardens. Even with a heavy dusting of snow, there’s still much to appreciate in this sprawling garden, the only one in North America specifically dedicated to conserving Alpine plant species. Explore the trails, stop by the exhibits at the Education Center, and, if you're lucky, your trip will coincide with one of the family-friendly workshops and activities that the garden hosts.
Until Next Time!
After a full weekend of snow-filled fun, scenic views, delicious meals, and so much more, Vail has undoubtedly left a good impression on you. While winter is known for its skiing and snowboarding, this mountain town is also a year-round destination with a wide variety of outdoor adventures waiting for you to enjoy on your next trip to Vail. Perhaps spring or fall? There’s never a bad time to visit Vail.
Jessica Poitevien
Jessica Poitevien is an international storyteller with more than a decade of experience in writing and editing. Born in New York, she caught the travel bug throughout multiple moves that brought her to California, Spain, Colombia, and her current home base in South Florida. She has visited over 40 countries (and counting!), including several solo trips. When she's not traveling, Jessica enjoys making social media content, trying new food, and acting as a travel agent for friends and family.
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