Vail becomes a snow-blanketed playground in winter, where families can play, relax and make special memories together. From toddlers bundling up for their first snowy adventure to grandparents taking in the serene peak views, Vail has things to do for everyone in your multi-generational crew.
Use this itinerary to plan group outings, kid-friendly fun and even some adults-only getaways with pre-planned childcare.
Day 1: Arrive & Settle In
Check in at Your Family-Friendly Accommodation
Ease into your vacation by cozying into accommodations that feel like home, with a touch of Rocky Mountain magic. Antlers at Vail in Lionshead Village welcomes families with roomy condos that have full kitchens for home-cooked meals (perhaps by a private chef?) and fireplaces perfect for snug nights in. At The Arrabelle at Vail Square, also in Lionshead, elegant suites give your family plenty of space to spread out, while the heated outdoor pool is a favorite for kids eager to take a dip — even when snowflakes are falling. For something a bit more private, Vail Residences at Cascade Village offers mountain-view homes where you can sip hot cocoa and gaze at the golden hour’s alpenglow.
Explore Vail Shops
Once you’re all unpacked, stroll through the villages’ storybook streets. Children will love the tempting displays of plushies, sleds and board games at Wishes Toy Store, while outdoor enthusiasts can find high-quality winter gear at Christy Sports. Then, treat the family to sweets at Fuzziwig’s Candy Factory or Rocket Fizz, where the shelves are brimming with specialty sodas, chocolate, gummies and penny candies.
Dine at a Welcoming Restaurant
End your day gathered around a table at Blue Moose Pizza, which has a casual atmosphere and freshly made pies that satisfy even the pickiest eaters. Try the buffalo-chicken pizza with the spicy sauce, cheddar and lots of bubbly mozzarella. For bold flavors and a fancier atmosphere, head to El Segundo, where the vibrant Mexican dishes include cheesy quesadillas and soft chicken tacos perfect for the kiddos. Meanwhile, parents will want to try specialties like the Wagyu Chili Colorado with red-chili-braised wagyu chuck, spanish rice, and fresh onions, radish and cilantro tucked into warm tortillas.
Day 2: Go Skiing With the Fam
Best Ski Schools for All Ages in Vail
Start your day on the slopes with lessons at one of the best ski resorts in the state. Golden Peak Children’s Ski School in Lionshead Village is the best ski school for young kids, where they can safely learn the basics in a fun environment. Vail Ski & Snowboard School helps teens, parents and grandparents sharpen their skills with private or group lessons — or start from the very beginning with intro classes for all ages. For family members with disabilities, the Vail Adaptive Office ensures that everyone experiences the thrill of carving through fresh powder with personalized lessons and adaptive equipment like sit-skis and mono-skis.
Beginner-Friendly Ski Runs for Multi-Generational Groups
After lessons, head to beginner-friendly trails (be on the lookout for green symbols by the runs) where your group can glide down together. Brisk Walk and Lost Boy are both green runs, for example. Once your family is ready for blues (the blue symbol means intermediate) and a longer run, Born Free winds from the top of the Eagle Bahn Gondola (#19) all the way down to Lionshead Village, giving your family plenty of time to take it slow and enjoy panoramic bluebird views. See Vail Mountain’s trail map
Day 3: Explore Beyond the Slopes
Non-Skiing Activities
Vail has plenty of activities to keep the fun going beyond the ski terrain. Zoom down sparkly hillsides on a snow tube with Sage Outdoor Adventures, which offers groomed runs for a super smooth ride. For a quieter day in the valley’s peaceful forestland, trek the frosty trails at Vail Nordic Center on snowshoes or cross-country skis.
Indoor Fun for All
Once everyone’s ready to warm up, head inside for some family entertainment. Challenge each other at Vail Village’s Deca+Bol for a rousing round of bowling and honey butter-covered fried-chicken sandwiches. For quieter fun, settle into a cushy couch by the crackling fireplace at Vail Public Library for storytelling sessions that little ones will love.
Day 4: Relax & Bond
Get a Vail Babysitter
While the tots enjoy sledding at the park, pizza nights and movies with trusted Vail babysitters, parents and grandparents can carve out some time for themselves. Whether you’re hitting the more challenging slopes or just want a romantic dinner, there are plenty of local caregivers — with comprehensive background checks and flexible scheduling options — that will allow you to plan some adults-only escapes.
Spa Days for the Adults
Step into relaxation at one of Vail’s luxurious spas. At RockResorts Spa, soothing couple’s massages, specialty desserts and bubbling hot tubs will melt away any stress for busy parents. Sonnenalp Spa surrounds you with towering mountain views and offers an oxygen bar to help you adjust to that alpine altitude. Schedule treatments like the heated-stone massage, which uses smooth river rocks to relieve tight and aching muscles.
Restaurants Perfect for Families
In the evening, come together for a meal that feels like a celebration. Alpenrose serves Bavarian-inspired dishes in a warm, family-style setting, with buttery noodles for the youngsters and beautifully spiced bratwurst for the adults. For a more casual vibe, head to The Red Lion, where the Kiddie Corner menu serves dinosaur-shaped chicken nuggets and PB&J sandwiches for the little ones and parents can dig into smoky barbecue-brisket platters.
Day 5: End Your Vail Vacation With Unforgettable Memories
Capture Family Moments
Before heading home, take time to snap a few photos. The covered bridge, draped in snow and bedazzled with colorful lights in winter, is a perfect spot for a holiday-card photo. Or stop by the Vail Square Ice Rink and capture the kids twirling against a backdrop of Tyrolean-inspired buildings.
Farewell Treats
Don’t start your journey back without a hearty breakfast. The Little Diner is known for its fluffy pancakes and marshmallowy hot chocolate, while Yeti’s Grind serves up fresh pastries, bold coffee and kid-approved snacks to keep everyone happy on the road.
Practical Tips for Planning the Best Multi-Generational Vacation in Vail
- Book early: Reserve lodging and ski lessons a few months ahead of your trip to secure your preferred options during peak season. Here are the wintry Vail activities you’ll want reservations for.
- Pack smart: Include warm layers, waterproof snow gear and entertainment for downtime.
- Use Vail’s free bus: Hop aboard for easy transportation between the villages and ski lifts.