Trip Report: Three Days at Keystone Resort

Brooke and I took our first big trip of 2016 to Keystone, Colorado.  We both love to ski, and Keystone holds special significance to us, because I proposed to Brooke at the top of the main summit in 2013.  Ski trips are notoriously expensive, with lift tickets, gear rental, and pricey food to consider, in addition to the standard flight, lodging, and ground transportation costs.  While some of the ski-related costs are unavoidable, we can at least offer suggestions to offset the other costs, using points & miles.

Air Travel/Transportation


Most of our domestic trips are on Southwest, because the Companion Pass is just a sweet perk!  The flight attendants are also nice, the boarding is generally very smooth, and the in-flight entertainment is free.  (Check out our Tips for Flying Southwest).  We departed Kansas City on Friday night and landed in Denver around 10pm.  We picked up our rental car from Alamo for the drive to Keystone.

There are a couple options for transportation from Denver to the ski areas, including shuttles from the airport.  We opted to rent a car, because we wanted the freedom to come and go as we pleased.  We also planned to visit some friends in Denver on the last day of our trip.  The cost difference was negligible between renting a car and taking the shuttle.

I found that various websites displayed vastly different prices for the rental car.  Kayak and Hotwire showed $65/day, but the Chase travel portal showed $28/day for the exact same cars and dates!  Be sure to check all options for a rental car!  We also opted to pay for the rental, instead of using points.  The Chase Sapphire Preferred provides primary rental coverage, and driving in snow seemed risky enough to warrant the insurance.


  • Shared Keystone Condo – $100/night x 3

Hotel options in the Keystone/Breckenridge area are very limited.  Fortunately, Brooke’s sister and her family were already planning a visit to Keystone.  They booked a condo and graciously allowed us to crash with them and share the cost.  During our initial search, we considered AirBNB options, which generally start around $100/night.  We also looked at the Holiday Inn Frisco-Breckenridge, but 35,000 points/night seemed high.  If you have a lot of IHG points, this could be a good option.

  • Staybridge Suites Denver Airport – 15,000 IHG points/night x 1

On the final night of our trip, we booked a room near the airport.  We had a 6am flight back to Kansas City, so we wanted a hotel that offered an airport shuttle.  We returned the rental car on the night before, to avoid being charged for an additional day.  The Staybridge was quite nice, and our room was HUGE.  We had a living room, kitchen, two bathrooms, two bedrooms, and three beds!  Too bad we were only there for 6 hours…


  • Skiing at Keystone


Obviously, the main goal of our trip was to ski the slopes at Keystone Resort.  After we arrived to the condo at midnight on Friday night, we quickly went to sleep, to rest up for the following day’s action.  We popped out of bed at 7am, chowed down some breakfast, and hit the Mountain View Sports ski shop at 7:55am.  We wanted to be first in line before the rush of Presidents Day weekend descended on the rental counter.  We were in and out in 15 minutes with our gear!  Tip – Save 20% on ski rentals by booking in advance on their website.

Once we had our skis, we loaded our EpicMix app (highly recommended) to check wait times at the various lifts.  We located the lift with the shortest wait time and headed that way.  Tip – Download the free EpicMix app to view resort maps, check wait times, track your ski stats, and view professional photos online.  Everything is tracked using the chip in your lift pass card!  Super cool!

Brooke Ski

Day One brought phenomenal weather!  Blue skies and 35 degree temps had me sweating in my ski jacket.  Brooke and I are, what I would consider, “intermediate level” skiiers.  We generally stick to the blue square, or medium difficulty, ski runs.  During the first day, we re-familiarized ourselves with the runs on Dercum Mountain and North Peak.  Our favorite run at the resort is Spring Dipper, and our least favorite is Mozart, due to the constant crowds and icy slopes (see video below – Wipeout at 1:29).

Day Two on the mountain brought four inches of fresh powder in the afternoon.  Snow showers moved in, and the temperature dipped a bit.  On this day, we covered 18,351 vertical feet of ski slopes!  Our path through the resort went something like this:

  • Summit Express Lift – Mozart
  • Santiago Express Lift – Anticipation
  • Outback Express Lift – Elk Run
  • Outback Express Lift – Porcupine
  • Wayback Lift – Prospector
  • Santiago Express Lift – Star Fire – first black diamond!
  • Ruby Express Lift – Spring DipperJaybirdHaywood
  • Learning Area to ski with niece and nephews at ski school
  • Peru Express Lift (with kids) – Silverspoon
  • Montezuma Express Lift (with kids) – SchoolmarmSchoolmasterJaybirdIna’s Way

By day’s end, we were beat, so we just hung around the condo and watched Netflix… Tip – If you have time to kill, watch all 5 episodes of “Vanilla Ice Goes Amish”… total Netfilx GOLD!

Piggy Back

By Day Three, we were tired and a bit sore, but still excited for more fresh powder!  It snowed another few inches overnight, so the mountain was blanketed in new snow.  We went all the way out to the Outback Peak again, before working our way back.  The new snow was so thick in some places, that it was difficult to stay upright.  Around 1pm, we called for a final trip down Spring Dipper to River Run.  We waved goodbye to the mountain, hopped in the rental car, returned our gear, and headed back to Denver.

Tip – Avoid lines and save up to 25 percent on your lift tickets by booking at!

Tip – If you have kids (12yrs and under), and you are staying at one of the Keystone Resorts, you are eligible for the Kids Ski Free Program!  This is a HUGE value for families!  Our niece and nephews had a blast.

  • Great Divide Brewing

Great Divide

We drove to Denver to meet a few friends (Hey Jared & Nick!) and enjoy some of Denver’s famous craft beer.  Our friends recommended Great Divide Brewing, so we grabbed a beer sampler.  I really enjoyed the Espresso Oak Aged Yeti, the Port Barrel Meow Barleywine, and the Hercules Double IPA.  I’m a bit of a craft beer nerd (if you can’t tell).  The taproom itself was simple, and they offer free hourly brewery tours during the weekend (limited to 20 people per tour).

  • Dinner – Wyman’s Pizza

Our last stop in the city was Wyman’s to enjoy some Chicago-style deep dish pizza with more friends (Hey Pat & Sara!)  The pizza here is serious business!  We mistakenly ordered a large to share among three people, and ended up with half left over.  This is truly deep dish pizza, with delicious crust and pounds of melty cheese stringing everywhere.  If you grab dinner here, I recommend the Ron Burgundy!

Total Trip Cost Breakdown

The following table breaks down our transportation and lodging costs.  As you see, we spent relatively little money on these items, which allows us to use our money for great experiences!

Item Points/Miles/Loophole Actual Cost
Roundtrip Airfare x 2 from MCI to DEN 12,477 Southwest Miles from the Chase SW Premier Card & Companion Pass (fees covered by gift cards from Amex Platinum $200 Airline Credit) $0
Rental Car – 3 Days $28/day paid with Chase Sapphire Preferred for free Primary Insurance $84
Shared Condo – 3 Nights $100/night – Sharing with Family/Friends can save big money! $300

The chart above covers our costs for getting there and staying at the slopes.  We could have done it more inexpensively by redeeming Barclay Arrival+ miles or Citi ThankYou Points for the rental car, but we wanted the primary insurance coverage provided by the Chase Sapphire Preferred.  While not free, $384 is still a great value for flight/car/accommodations for two people on a Keystone ski trip!  Additional costs will include gear rental and lift passes.  Use the tips above to save money on these items.

I hope you enjoyed our trip summary for Keystone!  Use your points & miles to offset your flight and lodging costs, so you can enjoy great skiing at this fantastic resort.  In my humble opinion, it is the best ski resort in Colorado!  Cheers!


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