Since this is our first winter together, we are learning about each other’s planning styles and figuring out our combined approach.

Start with, where do you want to ski?

First things first, you have to select your pass. We could and likely will do a whole other blog post on this topic when it’s time to purchase our 2020-2021 season passes. But since pass purchasing time is done for the year, we’ll share what we decided for 2019-2020 by considering where we wanted to ski, and how frequently we wanted to ski there. I realize that we are very fortunate to be able to afford more than one pass - skiing is something we both love and believe it is worth investing in our happiness. (Also, having a pass definitely motivates me on the "meh" days to ski just even a few runs. At the end of the season, I like to divide my total cost by the number of days I skied and see how low I can get my per day cost.)


  • The Utah resorts during the December blackout for base version
  • Winter Park, Copper and Eldora regularly as day trips
  • Big Sky because I had to cancel my trip there last year and am really looking forward to going back with Jacob (I lived there during Winter in 2011)


  • The opportunity to ski early and late season just can't be beat! We knew we were going to ski more than 7 days here so the pass was our only option. See our blog post from our first day in October for more about why we love A-basin.


  • Jacob's family has a trip planned to Vail, we looked at prices and buying an Epic Day Pass in early season was better value then using Buddy or Ski With A Friend Passes associated with his Dad's pass

Next, where do you want to go and when?

You want to go where the snow is when it is snowing, right? Yeah, we all do. Unfortunately, skiing is an activity that relies in big part on the weather. Because of this, there are two approaches in ski trip planning: the follow the snow and book last minute, or the book early and if the snow is bad you can always hike or find a brewery.

We mainly follow approach #2 - we plan trips to meet up with friends and family, ski a specific mountain or go because there is a good flight deal. Last year Jacob had fresh snow on all his trips but one, so I can only hope we are as lucky this year. The good news about the plan ahead approach is that you can often find inexpensive flights or accommodations.


  • Keep an eye out for flight deals. Jacob is a big fan of the Scott's Cheap Flights mailing list which sends you an e-mail daily with cheap flights. There is a free version and a paid subscription. Towards the end of October, in between conference calls, Jacob asked me "Isn't there a mountain on our pass just outside of Calgary? There is a Denver to Calgary deal on Scott's Cheap Flights today, want to go?" – my answer YES (three mountains) and YES (just tell me when)!
  • Plan a ski road trip. We are planning a ski road trip including Park City, Big Sky and Jackson - linking them together saves driving time (and gas money) rather than doing them each as an individual trip. Since we both work remotely (a la the "work hard" part in our blog name) we can spend a day remote we can spend a day working remotely in a larger city so we are not always paying resort prices. My favorite part of ski road trips is you can build in a little bit of flexibility to follow the snow forecast.
  • Fly on off days to save. Since we can work remotely, we can choose to fly on the least expensive day. But remember if you plan to do this that you should factor in the cost of accomidation and food to make sure you are actually saving – or plan it to a city where you have friends to visit to make the most of your time.
  • Understand how to earn and use frequent flier/loyalty programs. I used to travel Monday through Thursday for my consulting job, one thing you learn being a road warrior is the travel points game. In June 2018, I earned the companion pass on Southwest, arguably one of the best perks around. It means that I can bring a companion with me for just the fees on any Southwest flight that I fly. My companion pass expires December 31st, so we booked a December ski trip to take advantage of it one last time. I've always tried to stay consistently with one hotel brand but with ski towns that can be tricky. On our trip to Australia, we started booking rooms with and they have their own loyalty program, after 10 nights we will have a free stay. Looking forward to redeeming our first night sometime this ski season!
  • Carpool (or take the bus) for day trips. We both have done ski condo shares in the past, but with all of the travel we planned for this year we passed up that opportunity (range between $250-300/month per person). So we will be day tripping mostly when we are local - as much as possible we will carpool since it is good for the environment and good for your wallet if passengers chip in for gas. Also, there is also a Regional bus to Eldora ($10.50 per day pass) which we will definitely be using. And one just started this season on weekends to Arapahoe Basin ($25 round-trip on Snowstang). [Note from the RTD Website: All ski equipment must be placed in a ski bag when boarding any bus. Ski bags are not required on Regional buses when skis are placed in lower baggage bins.]

Finally, just book it!

If you love to ski and know you want to take a trip this ski season, schedule it and commit. It is easy to fall into the trap of worrying about the snow and conditions or to say "I'll go next season", but we have never gone on a ski trip and thought - wow I wish I had just stayed home. Find a buddy or go solo - but get out there!

Comment on the Instagram post below with where you're headed to go this ski season. Let us know if you have any questions about the mountains we mentioned, happy to help. Wishing you smooth travels and powder days!