Winter Activities – Minimized Cost, Maximized Fun

The PIE family members are examples of those rare people who look forward to a New England winter with excited anticipation. 24” snowfall? Bring it on! Cold and windy? Wrap up! It might be fair to say that despite being New England residents for 18 years now, the novelty of having a true winter with lots of snow has not worn off. When winter hints at arriving, our thoughts turn to skiing.

Mr. PIE and I learned to ski as adults when we came over from the U.K. 18 years ago. The bug bit us hard, and we have only missed two ski seasons since then. Both years due to me being pregnant (you just don’t seem to be able to buy maternity ski wear!) The small PIE’s both had their first ski lessons at 3 years old, and are now very close to being able to out-ski Mum and Dad.

Needless to say, being able to continue our family hobby now and in Early Retirement is tremendously important to us. It’s also needless to say that skiing is a particularly expensive pastime. Day lift tickets in New England go for around $100 these days; and at the big mountains out West the prices are heading towards $150. That’s before you even start to think about gear, lessons, transportation and food.

So how does a costly hobby like skiing fit into the PIE family budget? Like everything else that we spend money on and budget for we are intentional in our spending. We’ve learned some tricks over the years and are now, even more consciously looking into the most cost-effective way to be able to do what we love to do. I’m going to share with you some of the tactics were have used to minimize our ski spending, and to get the most value out of what we do spend. This will cover both our local New England skiing this winter, and the trip we have planned to Jackson Hole in February 2017. If you’ve read much of our blog so far, you won’t be surprised to hear that many of our strategies involve some extensive planning ahead.

Here are the four areas I’ll delve into:


Jackson Hole Flights – Air Miles and Planning Ahead

Let’s first turn to our vacation to Jackson Hole in February 2017. We have skied there many times before, and if you’ve ever been to the area you’ll understand the tug the region can exert on you to return – again and again.

For our 2017 trip we have used United Airlines miles to cover the cost of 4 return tickets from Boston to Jackson Hole and paid the princely sum of $45 in taxes. Our United Airline miles were a combination of some travel hacking (Chase Ultimate Reward points and Chase United Airlines credit card) helped along by some accumulated business miles from Mr. PIE. We booked these flights back in April this year to maximize availability and choice. It’s worth noting that a quick search for today’s prices to Jackson Hole for four people comes out to $4,613. A definite win for travel hacking and planning ahead.

Jackson Hole Lift Passes – Shopping Around and Planning Ahead

It was a pure coincidence (or probably some clever targeted advertising) that I noticed an ad for The Mountain Collective Ski Pass in my Facebook news-feed last April. It seemed a little too good to be true as I clicked though and found what seemed to be a fabulous deal for the family’s Jackson Hole lift tickets.


The Mountain Collective offers a 28 day pass covering 14 ski resorts in the US and Canada. Back in April this year they were offering a great deal for the 2016/17 season. $379 for Adults and $1 for kids (yes, you read that right – $1!!) would give all four PIE’s:

  • 3 full days skiing at a destination of our choice
  • All additional days at 50% off ticket window prices (for a total of 28 days)

We quickly got online to compare this to buying tickets the traditional way – online at the Jackson Hole Mountain Resort web site. Tickets through the Jackson Hole website would cost us $1,780 for 5 days skiing. Using the mountain collective pass would total $1,198, a saving of $582.

It’s worth noting that today the Mountain Collective pass prices are $419 for adults and $99 for kids, and includes just 2 full days followed by 50% off additional days. Another win for shopping around and planning ahead.

You have to ski hard to earn cocktails at The Four Seasons

Lodging in Jackson Hole – Travel Hacking and Planning Ahead

The Jackson Hole lodging scene is expensive to say the least. On-mountain hotels such as the Four Seasons cater to the fur collar and perfect hair crew (do you even ski?!) with ski valet services and outdoor fireside cocktails (OK, the cocktails are good!) In town there are some more realistic hotel and motel options, but for a family of four finding a hotel with a reasonable amount of space and a small kitchen is tough. We’ve looked into various options over the years including VRBO condos and houses. We consistently come up with the same answer: The Jackson Hole Lodge.

The Jackson Hole Lodge offers small town house style family suites, with two bedrooms, small kitchen, 2 ½ bathrooms, washer and dryer and all the other amenities you’d expect to find in a condo. An added bonus is a newly renovated pool. They are simple, clean and functional – and most importantly very competitively priced even compared to a similar sized VRBO rental. Back in April we reserved our rooms for $1,597 for 7 nights. These suites are fully booked now, so if we were still looking for Jackson Hole accommodation we’d likely be paying more than that. We estimate around $2,100.

To bring the cost of our hotel stay down we’ll be using a total of $780 from some ‘fixed value’ travel credit card rewards (Barclaycard Arrival Plus and Bank of America Travel Rewards). Our hotel will cost us $817 for 7 nights. Another win for travel hacking and planning ahead.

Planning our next ski vacation while the snow was still melting on the ground from the previous winter, instead of waiting until the first flurries were seen for this winter, has saved us a whopping $6,433!


Local Skiing Lift Passes – Planning Ahead

But what about local skiing? We have a vacation home in the mountains after all, and as usual we intend to clock as many mountain days as possible this winter. This will be the third season that we have purchased season passes for our local mountains. Each time we have purchased them we have done so at the very lowest price for the year, and as you might expect, that’s while the previous season is barely even thinking about winding down.

We bought our 2016/17 season passes in March this year for the PIE family, at a total cost of $1,996. Today those same passes would cost us $3,596.

If we ski 20 days this coming season that works out at about $25 per person per day – a fantastic deal. However, we tend to think of our season passes as somewhat more than just a dollar value. Having a season pass allows us to ski for as much or as little of the day as we want without feeling that we have to maximize the value of a day pass. It gets us onto the mountain when conditions aren’t optimal and most other folks stay away. We’ve had some great ski days that we wouldn’t have otherwise paid for.


Local Skiing – Kids Equipment

As each ski season approaches we wonder what the best way to equip the Small PIE’s will be. Over the past three seasons we have picked up seasonal equipment leases for them. This includes boots, bindings and skis for the whole season for $175 each. The benefit here is that they get fitted correctly for new equipment each season. If they have a growth spurt during the season we can swap out gear at any point for no additional cost. We’re firm believers that proper fitting boots are the most important part of your equipment, and this has lead us to continue to lease instead of buying their gear. While a pair of skis should last a couple of seasons and be passed down from older PIE to younger PIE, we value well fitted boots over hand-me-down boots that are not quite right.

It’s hard to estimate the cost of buying skis and boots for the boys, allowing for handing down and possible trade in value. We have come up with an estimated cost that turns out to be pretty similar to leasing. The additional benefit of leasing is that the package comes with free season passes for the kids to another local mountain. That’s a value of $600 to $800 – a win for the lease and a pretty good reason not to start buying their equipment yet!


Local skiing – Mountain food

The Stanley Rocket

In our less frugal days we would have thought nothing of stopping by the ski lodge for hot cocoa, snacks and lunch throughout the day. As we started skiing more frequently and became more aware of our expenses it became obvious that we needed to change our habits. That’s to say nothing of the on-mountain food quality and options. A burger, bowl of chili or slice of pizza is OK every now and again, but this is expensive and not particularly good food. We could easily spend $40-$50 a day on family food at the mountain.


As you might expect, this has gradually changed and we are now pretty good at packing our own food for the day. A major player in this change has been the discovery of the Stanley brand vacuum flasks – thanks to a gift from my brother. We now regularly fill the ‘rocket’ as we call it with hot cocoa or homemade soup. We’re looking forward to using our new ‘mini-rockets’ this season too, filled with pasta, chili, or pretty much any warming meal you could imagine.


Skiing isn’t cheap. Traveling to awesome destinations like Jackson Hole isn’t cheap. If we want to continue our family hobby into early retirement all of these tricks and tactics will become even more important. We estimate that a combination of planning ahead, shopping around and general frugality has saved us around $9,000 over full price costs this coming season. Good thing too –  we’re not planning on quitting skiing due to high costs any time soon!

What winter activities do you enjoy? How do you keep the cost of your hobbies under control?




  1. We tend to go warm for our winter vacation like the Caribbean. That being said we also tend to pick less traveled locations. This year we’re hitting Martinique for the second year in a row. Prior years have been the Keys and Miami. Typically we do like you and start planning out miles for flights early early. Couple that with using airbnb for cheaper lodging. The last step we use are cash back cards, typically I save our cash back for trips.

    1. We love the Keys and have spent some wonderful vacations in Islamorada – what a beautiful spot!
      Cash back cards really are the way to go if you’re not staying in one of the big chain hotels. Jackson Hole has very chain few hotels that we could use points for. The frustrating thing about cash back cards is how many you have to go through to even get close to what you need for lodging costs. I guess every little helps though!
      Thanks for stopping by!

    1. Thanks!
      We’ve not been in the summer time, it’s on our list and I’m sure we’ll get to it eventually. It can even snow in June, so I can imagine it’s not often super hot there.
      I’ll try to oblige with plenty of pictures!

  2. Very impressive savings! We also stopped paying full price long time ago.
    For ski passes, we follow your strategy of buying early. It’s in a different family of resorts, though, but with the same impressive savings relative to paying full price. Four days of skiing already recovers the deeply discounted pass.
    For hotels, we normally do the Priceline “Name Your Own Price” and then redeem the credit card points. That gives us around $1,000 a year in free hotel stays. Another option we have used in the past is the timeshare membership of the in-laws. Last year we stayed for a week at a nice 2BR condo (with small kitchen) in the ski country, walking distance to the lift, for $300. I’m pretty sure the economics of timeshare is bad for the members but it definitely worked out well for us. 🙂
    All of that, of course, was in a resort not quite as posh as Jackson Hole. But: Jackson Hole will be on the short list for summer 2017 (Yellowstone and Grand Teton NPs) and we will definitely keep the Lodge in mind. Any other Jackson Hole recommendation for lodging in the summer? I’d be willing to stay a little bit outside of JH. Thanks! Cheers!

    1. Hi ERN, thanks for the comment
      We’ve not delved into Priceline yet – that’s certainly something we should take a look at. I’ve always been a bit nervous about it, but as I learn more about travel hacking I realize there are a few tricks that can be applied.
      Someone else’s timeshare really is the way to go! It’s a bit like having friends with a vacation home is almost as good as having one yourself! 🙂
      Jackson Hole has a posh reputation, and that side of it is certainly prevalent. However that’s balanced out by a more realistic side loved by those who live to ski. I think they have stopped the practice now but the parking lot at the mountain used to be the classic place to find the ‘ski bum’ camper vans!
      If you want to stay further out when you go, you might look at Driggs Idaho. not too far out, a beautiful drive and much more reasonable than in town.

  3. Did the Jackson Hole travel authority put you up to all this? Now I’m gonna have to start looking into booking time in Wyoming!

    You PIEs killed it with the plane tix – a nearly incalculable savings!

    Our winter activities vary a great deal. With Little Libre still doing the first-year thing, we’ll be subdued this coming season. But who knows? Maybe we’ll end up crowding y’all in the Jackson Hole Lodge sometime soon! Great post as always, and thanks!

    1. Thanks FL!
      Not paid by WY at the moment, but if they happen to find this little blog and compensate us we’ll be happy to accept!
      Tiny ones do make winter activities tough. We were lucky enough to vacation with Grandparents when oldest PIE was 1, and that got us out on the snow some.
      Mr. PIE says you really should check out Jackson in the winter, the powder is awesome!

  4. Wow – what impressive numbers! It’s amazing what you can save with some early planning. We are like Full Time Finance above and prefer to spend our winters getting away from snow! We’ll be heading south (to Sarasota, Florida) in 13 days (not that it is even that cold here yet – 62 this week??) We only pay $11.20 each for taxes/fees for flights (Southwest) and we have a Companion Pass so we only use miles for one of us! We also are paying for the car with Ultimate Rewards points. So very little spent this trip! We are going back at Christmas too. Same cost for plane tickets but we’re paying for the car this time. Great post PIE’s – and enjoy the snow! I’ll enjoy the pics like Julie said!

    1. Thanks, I can see have to dust off my non-iphone camera!
      Isn’t it wonderful when a trip comes together for so little money! you’ve really got a great deal there with the Southwest pass. I know it’s a popular one for the travel hacking community and probably something we’ll pursue eventually. We’re busy collecting transatlantic BA and AA points at the moment.
      Sarasota in the winter also sounds wonderful, have a great time!

  5. Speaking our language! I’m seriously impressed by all the different ways you have found to reduce the cost of this ridiculously expensive pastime. You are making me wonder if, perhaps, we moved to a ski destination town simply to avoid having to jump through all of those hoops. Because when skiing is at home, it is a whole heck of a lot cheaper! 😉

    1. Hi Ms ONL, thanks for the comment,
      yup, non-destination skiing is certainly the more frugal way to go. I wonder how much destination skiing we will do when we permanently move to our mountain home? I have a feeling we’ll still be fitting in some trips out west, or South America, or something like that!
      I’m currently trying to justify a new pair of skis for myself. You’ll be horrified to hear that I have one pair and I’ve had them for 10 years. They’re pretty awesome but I’ve had a taster of some newer ones, and you know how that goes. Maybe in the end of season sales ……..

  6. Impressive savings with planning ahead! nice job.

    Ski is sure my favourite winter past time. As the highest point in belgium is below 700 meters (0,435 mile) there is little snow here. So, we go to Swiss, by car. Yes, not the cheapeast. We are going with an organisation that offers a 7 day package (meals & drinks in restaurant, material, passes, ski lessons in Dutch or the kids, kids entertainment when they do not ski and in the evening) Transport is by car and what you drink in the bar is on top. We like it.

    1. Hi ATL
      That sounds like a pretty good package deal – especially with lessons included. Can you believe that I have never skied in Europe?? Mr. PIE has as he went to Italy at age 14 on a school trip. European skiing is certainly on our list for the future. Maybe some kind of package deal is the way to go for that.
      Thanks for stopping by!

  7. We’re also fans of winter 😀

    For the past few years, this has just meant taking walks on the nearby trails with Fluffster, but I’m hoping one of these days we actually look into snowshoeing or cross country skiing.

    1. Yay for New England winters! We’re trying to get ourselves kitted out for snow shoeing and some winter hiking. I think we’ll have to practice snow shoeing in the back yard though. None of us have done it before!

  8. I enjoy winter gardening and starting a fire when the temps drop below 50. The peas, turnips, carrots, rutabagas, collards, and cauliflower are all sprouting nicely. And I am battling with an invasion of leaf eating caterpillars with my peas right now. Oh wait, you mean winter in cold areas of the country. 🙂

    I love snowboarding, never tried skis, and snowshoeing. Mrs. SSC skis and wants to get into Nordic skiing and/or snowshoeing. We would probably employ similar tactics to reduce costs if there happens to be downhill near wherever we end up. Since the kids have come along, we’ve just had one ski trip to Vermont. Sigh…

    The season pass purchase at the end of the season is a great time to save.

    1. Ha ha! Yes, our winter would be around 50 degrees lower than your gardening temp! It takes a little getting used to each year as my body’s thermostat readjusts.
      I’ve never snow boarded. I’ve got nothing against trying, I think it would be fun. The idea of being at the bottom of the learning curve again isn’t so nice though!

  9. Those are some nice, juicy savings. You’ve done an excellent job figuring out how to keep doing something you love, something that your whole family values.

    I’ve tried skiing and snowboarding one time each. Both times I was firmly at the bottom of the class. The time I tried to snowboard the instructor told me to keep trying the first thing she taught us while she moved on with the rest of the class. I spend the _entire_ class trying step 1 and failing and falling and cursing. Lots of cursing. Sigh.

    1. Hi there, thanks for stopping by!
      Sorry to hear you didn’t have a great experience. So much of how quickly you pick it up in those early lessons is down to the instructor. Most of the instructors we have come across have been great, but there’s certainly been a few questionable ones!
      I was impressed to find that this year out local season passes had actually gone down in price from last year, what a nice surprise!

  10. Wow I wouldn’t have imagined the savings to be so huge buying early! Good for you folks for taking advantage, you got some great deals. I love the Stanley rockets, too.

    We don’t live too close to any skiing mountains in Charlotte unfortunately, I’ve skied a half dozen times and really enjoyed it. There are a few slopes in western Carolina though. I’d love to get my little one started young skiing, such a fun family activity! Enjoy the slopes this winter!

    1. You’re right. The savings are huge. It makes me wonder who pays those exorbitant prices later on! Young is the way to go with getting started skiing. I’m so jealous of my kids, wish I’d been able to start at 3, not 25. I’d be such a better skier!

  11. I haven’t skied in years but used to during breaks in college since I lived in New England. Midwest is a lot flatter now 🙂 I used to keep costs down by buying student lift tickets, borrowing gear from friends, renting instead of buying skis/boots.

    1. Yup. Hard to ski in the Midwest! I didn’t go into costs to equip adults for skiing. At least our gear lasts longer, but always fighting the wants vs needs of need cool stuff!

  12. I’m glad you guys love winter so much Mrs PIE.

    I have to say that, as Australians, we don’t really get a ‘proper’ winter. It is possible to go skiing in mountains, but it’s a long way away for us. We prefer to stay at home lol! Australian homes are not built for winter. Double glazing is not common here.

    I do like the flasks, coats etc It makes you feel very cosy. 🙂


  13. Hi Tristan!
    one of the things I love about the North East US is the distinctive seasons. I’ve never lived anywhere that was truly lacking a seasonal change. Not sure what I’d make of it. There’s something very satisfying about hot cocoa on a cold day!

  14. I have terrible knees so as much as I’d love to snowboard/ski it’s no longer in the cards for me 🙁 With that said I still like to go snow tubing with my son. Watching they joy on his face playing in the snow is what I look forward to the most 🙂

    1. Oh we love tubing! If there something that’s going to make you feel like a kid then that’s it. I love to see the kids and adults alike being silly on the tubing hill.
      Sorry to hear about the knees – that would frustrate me a lot!

  15. It still is a expensive trip, but boy, did you guys do a good job at limiting the expenses. Seriously impressed with the “savings”! Have a great time you guys.

    1. Yes it is an expensive trip. The fact that we are lucky enough to be able to choose to spend our money on this is not lost on us. That’s what a trip like this is for us: intentional spending on what we love to do.
      In years gone by we would not have been so aggressive about pursuing ways to minimize all of those costs. These are ‘savings’ in the true sense of the word as now that money goes to our Vanguard investments.
      Thanks for stopping by!

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