Your 7-Day itinerary for the Perfect Winter Vacation in Big Sky, Montana

Your 7-Day itinerary for the Perfect Winter Vacation in Big Sky, Montana

It can be overwhelming when you come to Big Sky because there is just SO MUCH TO DO! Luckily, we live here full-time and can give you the rundown of what you absolutely can’t miss during your Winter Vacation in Big Sky, Montana.

Our winters can be pretty hectic trying to fit in all the skiing, snowshoeing, snowmobiling, sleigh rides, dinners, etc. And we want you to enjoy the beauty to its full extent!

Our first two big recommendations are to:

  • Pack plenty of layers, Winter weather changes frequently!
  • Be sure you BOOK in advance as space is limited for every activity here.

If you are looking for non-stop adventure in Big Sky this 7-Day itinerary for the Perfect Winter Vacation in Big Sky, Montana is for you:






Get to Big Sky

Thai Basil for lunch and get ahead of Altitude sickness, stop at Reset to get your body ready. 

Lone Mountain Ranch Sleigh Ride Dinner


Breakfast on the go.

Skiing at Big Sky Resort (All Day)and Montana Jack For lunch.

Après at Umbrella Bar, Dinner at Peaks Chophouse.


Breakfast on the go.


Stop at Reset to keep your body going for the next few days! Eat at Block 3 Steakhouse for dinner.


Breakfast on the go.

Ski Day at Big Sky Resort and have Lunch at Everett's 8800

Relaxing Dinner. 


Late breakfast at Cafe 191.

Snowshoe Hike

Riverhouse + Live Music


Brunch at Cortina 

Start your Ski Day from Montage  

Montana Dinner Yurt hosted by Big Sky Resort 


Breakfast you have not visited from above.

Winter time fly fish OR horseback ride OR Spa Day. Visit the corral after for a late lunch

Dinner in town.


Sweet Buns

Leave Big Sky

**Note, depending on where you are staying, this may change. 

If you are here at the right time, you might get to experience some of our amazing annual events. 

Breakdown of your 7-Day itinerary for the Perfect Winter Vacation in Big Sky, Montana:

Tuesday: Arrive in Big Sky


  • Fly into Bozeman Airport
    • Option #1: Rent a car 
    • Option #2: Schedule private transportation (recommended due to winter driving conditions) 
    • Option #3: NEW JSX Air Shuttle
  • Stop to get your supplies for the week. 
    • Big Sky is 1-hour away from the “Big City” so stop now to get a few things. Here are our recommendations: 
    • Sunscreen (yes you still need it in the winter)
    • Water
    • Snacks and drinks
    • Any little travel things you may have forgotten at home (charges, headphones, etc.)
  • Arrive in Big SkyNeed a cup of coffee to get you through the long travel day? Stop at Caliber Coffee (Open until 3pm) or Cowboy Coffee (Open until 6pm).


  • After you get settled head to our new favorite Thai restaurant for a quick sit down or take away. If you prefer something other than Thai, here are a few other great options!
    • ByWom - Weekday Lunch 
    • BlueMoon - Weekday Lunch 
    • The Rocks - Weekday Lunch
  • Stop into the Big Sky Resort storefront (located next to The Rocks) to pick up your passes before you head to the mountain. This save you time and you can get right on the lifts! 
  • If you are from below 3,000 feet you are at higher risk of Altitude sickness. Stop at Reset to get oxygen.
  • Head back to your hotel, get some water, change into your Montana Chic (and warm) attire, and get ready to head to Lone Mountain Ranch.


  • Arrive at Lone Mountain Ranch for their sleigh ride dinner, an amazing family style experience featuring entertainment and a prime rib three course meal. Remember to purchase a bottle of wine in advance as there are no liquor sales once you arrive at the cabin. (BYOB is not allowed) 

Wednesday: Skiing at Big Sky Resort



  • Get to Big Sky Resort.
    • The parking options are fantastic, and there is a little shuttle to get from your parking spot to the base area.
    • You can always take Skyline, the free bus system from Big Sky Town Center (by Hungry Moose)
  • If you haven't already, pick up your pass for the week by heading up the stairs, going straight to the “Pass Pick Up” window, or use one of the new digital “Skycard Express”l kiosks. 


  • Stop at Montana Jack for lunch when you get hungry, a great spot for burgers and tons of local beer and a really fun atmosphere. There are no reservations but you can always hop on the waitlist right from the lift! 


  • Après at Umbrella bar is always a fantastic atmosphere! Right at the base of the Mountain Village, there are shot skis and 360 degree views of the mountain. 
  • Peaks chophouse is a fantastic option for a nicer dinner here in Big Sky. 

Thursday: Snowmobile in Big Sky



  • Hop on your snowmobile for a day of high octane adventure! Head up Buck’s Ridge for amazing views and wide open valleys to rip through. There are two snowmobile tour options in Big Sky.
    • GPS guided: Summit ATR Snowmobile
    • Guided Tours: Canyon Adventures
    • Don’t forget to bring: Sunscreen (we sit roughly 6,500ft. Above sea level, you need it) water, and snacks (full-day trips have lunch, but you want to keep yourself fueled up!) 

*1pm (if you do a half-day) or 3pm for a full day 

  • If you are feeling sore (or think you might be) head to Reset to get some amazing recovery and prevention services.


  • Dinner at Block 3
  • Amazing selection of Montana whiskey to go along with some fantastic wild game options like bison and elk, and of course your traditional steaks as well!

Friday: Second Ski Day at Big Sky Resort


10am - Ski Day (See previous ski day for how to get to mountain)


  • Lunch at Everett’s 8800. This is Big Sky Resort’s only on-mountain restaurant. Make sure you have a reservation! They rarely have walk-ins available.

*4pm Get back to your hotel

  • Take a shower and get ready for dinner.
  • If you are feeling sore (or think you might be) head to Reset to get some amazing recovery and prevention services.

7pm - Relaxing Dinner 

Saturday: Snowshoe Big Sky

 9 am

  • Sleep in a little, recover from the last two days.
  • Head to Cafe 191 for the best breakfast of your lives.


*4pm Get back to your hotel

Take a shower and get ready for dinner.


  • River house live music
  • Great views, music, food, and it’s definitely a Local favorite.

Sunday: Final Ski Day in Big Sky

  • Sunday’s in Big Sky are quiet. We like to relax, rejuvenate, and enjoy the outdoors. 


  • Sleep in a little and recover. We know we have made you sprint the last few days, so recover. Head to one of the following for Brunch 
    • Cortina 
      • If you are already at Cortina, might as well stay the day and ski right from the Montage! It gives you an opportunity to see a different area of the mountain that you have probably not seen yet.
    • Block 3 (only on Sunday Brunch) 
    • Blue Moon Bakery (Casual, baked goods, take and go) 


  • If you are feeling sore (or think you might be) head to Reset to get some amazing recovery and prevention services. 


  • After your third ski day, get ready for a one of a kind experience.
  • The Montana Dinner Yurt is another family style dinner featuring a transportation view snowcat. 

Monday: Dealers Choice



Fly fish in the Gallatin River


Horseback Ride

  • Jake’s horses is the only winter time horseback outfitter, but it is an amazing opportunity to ride into the outskirts of Yellowstone National park.


Spa Day

  • Reset Lounge is a great place to refresh from the jam packed adventure you experience here. Book an appointment early so you don’t miss out!
  • Big Sky’s peaceful mountain ambiance is embodied in every detail at Spa Montage, from a restful indoor pool area to sophisticated spa amenities. Spa at Montage


  • Early dinner / late lunch.
  • Head to the Corral for an authentic Montana feel, great burgers and better people! 



Tuesday: Travel Day.

Thanks for coming to Big Sky! We hope you got an adventure-packed trip and now you can go home and recover from your vacation. 

If you want help with what to do on your Winter Vacation in Big Sky, Montana, give us a call, we are happy to chat about how to get the most of your Big Sky Vacation. 

Don't wait until the last minute to plan your Winter Vacation in Big Sky, Montana, start planning trip now. 


Matt Zaremba
Sales Associate
"Live Big. Live Local."
[email protected]

Allen Potts
Sales Associate
"Find Your Adventure"
[email protected]


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