The Perfect 3-Day Big Sky Winter Itinerary

Big Sky Vacation Rentals offer a hand-picked selection of over 125 luxury vacation rentals in prime locations throughout Big Sky. We’ll find you the perfect home to suit your Big Sky vacation itinerary and assist with vacation planning to ensure your 3-day getaway to Big Sky is a special experience. 

To help you plan your stay, our local team has put together the best of Big Sky from dining, après-ski, to the best outdoor activities! Here are our suggestions for unique ways to experience the best of Big Sky in just three days.

Day 1 – A Warm Welcome to Big Sky


Begin your first day in Big Sky with a classic, hearty breakfast at the Carabiner Lounge overlooking the slopes of Big Sky Resort. Open daily from 6:30am this will not have to interfere with your on-mountain time! If you’re still settling in, start the day off slow with fresh coffee and homemade waffles prepared in your modern kitchen from the comfort of your Big Sky vacation home.

Ski Big Sky Resort

You’re fueled up and it’s time to hit the slopes at Big Sky Resort. Save time and reserve your lift tickets early! Big Sky boasts 5,850 acres of terrain and an average of 2 acres per skier, with fun and challenging slopes for every member in your travel pod. 

Slopeside Lunch

If you’re staying slope side you can always stop home for lunch, but we have a few on-mountain suggestions for a refuel. For a quick lunch, the best local meal deal on the mountain and legendary hot dogs, head to Yeti Dogs in Mountain Village or take your time and enjoy homestyle comfort food and a local brew at Westward Social in The Exchange.

Après Ski

After a long day of warming up your ski legs and cruising some of the greatest snow on earth, enjoy slopeside après ski with the best Montana craft brews on tap, signature cocktails and panoramic views of Lone Peak at the Vista Bar in Big Sky’s inviting food court overlooking the Mountain Village Plaza. 

Dine Out in Big Sky

Whatever tantalizes your taste buds, you’ll find it here in Big Sky. Experience the authentic flavors of Northern Italy at the award-winning Michelangelo’s contemporary bistro, sample Big Sky’s best sushi at the Blue Buddha Sushi Lounge or feast on drunken noodles and tasty Thai at Thai Basil.

Day 2 – Unique Big Sky Adventures


Pick up a coffee to go and breakfast sandwich or dine-in for local farm-to-table fare at Cowboy Coffee, an intimate eatery in Big Sky. You’ll need plenty of carbo loading for your day of outdoor adventures in Montana’s Big Sky country. 


Snowmobiling is one of the top winter activities in Big Sky and the best way to explore the remote Montana wilderness is by snowmobile. Canyon Adventures offer half and full day guided backcountry trips near Big Sky or escape the crowds and discover the beauty and natural wonders of nearby Yellowstone National Park on a guided or self-guided snowmobiling tour.

Après Ski

A day of wilderness adventures is likely to leave you shattered so you may want to recoup and enjoy après ski curled in front of the fire or stargazing from your private hot tub. But, if the Big Sky après ski scene has you hooked, the Block 3 in Big Sky Town Center has a daily happy hour with delicious spiked hot drinks, après ski cocktails, elevated pub grub and a laid-back atmosphere. 

Ride a Snowcat to Dinner

For a unique backcountry dining experience, we highly recommend the 3-course candlelit dinner at the Montana Dinner Yurt. Ride a snowcat through the peaks of Big Sky to a secret location on Lone Peak for delicious fireside dining, live acoustic music, torch-lit sledding for the whole family, and the most spectacular stargazing in Big Sky.

Day 3 – Back on the Big Sky Slopes


Start your day slope side at the Vista Hall food court on the upper level of The Exchange in Big Sky Mountain Village. The Café & Bakery is a European style coffee shop and café serving freshly roasted illy coffee, smoothies and a selection of breakfast pastries for hungry skiers to start their day the right way. Of course, coffee and croissants as you watch the skiers on the slopes from your private hot tub (or pillow) sounds equally enticing.

Back on the Big Sky Slopes

Big Sky boasts the biggest skiing in America, so there’s still plenty of terrain still to cover. The world’s most advanced chairlift makes it easy and quick to explore the vast terrain of Big Sky from the easy groomers to the expert terrain at the summit of Big Sky’s iconic Lone Peak. 

Slopeside Lunch

Ski over to the Madison Base Area on the Moonlight side for a slope side lunch at the Headwaters Grille. On Big Sky’s bluebird days, you can dine on the outdoor patio or stay cozy and watch the skiers and boarders from a window table while you savor salads, soups, grilled farm-to table specials and burgers or chicken fingers for the kids! 

Cross Country Skiing

Explore the beautiful scenery on over 85 kilometers and 2,200 vertical feet of groomed cross country ski trails right out of Big Sky. Lone Mountain Ranch was voted #1 Nordic ski destination in North America in Cross Country Skier magazine and certified instructors available, they invite skiers of all abilities to venture out on the trails.

Big Sky Brewery Experience

Beehive Basin Brewery is one of the top après ski spots in Big Sky and a fun place to wind down after a day on the slopes. Grab a pint, fill up a growler or sample a flight of hand crafted Montana beer while soaking up spectacular views of the Big Sky landscapes. 

Dine in a Historic Mountain Lodge

Take a scenic drive to Lone Mountain Ranch for a fine dining experience in the historic mountain lodge. Sip on one last après ski cocktail in the saloon bar and continue your evening at the Horn & Cantle for an authentic Big Sky culinary experience.