Travel Planning 101

I have planned our travel for as long as I can remember. At first, I would use Expedia or Costco Travel to bundle my deals and make sure I was doing it “right”. Planning a trip this way helped me learn all the components of trip planning. I use the same strategy when planning a point trip. Here is my thought process. There is no wrong/right way to do this. This is what works for me.

First - Airfare

We chose a destination. Airfare is usually my biggest expense (with a family of four) so I start there. For example, our family loves to ski. We go every year. I start pricing flights to see where we go and how many points it will take us to get there. We usually fly Southwest, so I collect Southwest points and Chase Ultimate Rewards. We buy Epic passes each year so that limits our locations. This year I looked at Reno to Ski Tahoe, Denver to Ski Keystone and I did search Vancouver to ski Whistler. I tried hard for Whistler we haven’t been there in many years but I couldn’t make it work. I wanted the points I would need to use for it to go toward my trips to Europe.

Now that my kids are in college, our ski trip dates are set in stone. I realized very quickly that flying to Denver would be the most affordable option. I went ahead and booked our flights on points to Denver before I even looked at lodging. I did this because if you book Southwest flights with points and cancel you get your points back. I also knew flights change prices constantly and if I could get all of us there on points I should book now. I also knew if they dropped I could “change” my ticket and rebook the same flight and get points back! I will add this is not the case with all point flights but it is with Southwest.

Second - Lodging

There are lots of great places to ski in Colorado. We have been to quite a few but we really like the ease of getting to Keystone. As with any trip, my first step when looking at lodging is always to see if there is a Hyatt. Hyatt has terrific deals on points travel. It is my number one search for lodging for any trip. If they don’t have a Hyatt, I will go down the list of Hilton, then Marriott. I do this because Hyatt and Hilton waive resort fees when you book with points. Marriott does not. These are the only points I keep although I have thought about IHG for 2025.

For our ski trip this year, I checked the Hyatt Place Keystone which is 18k points a night. This is a fantastic deal. However, we need two rooms at this stage in life. I could not get the point price on the room we wanted the King Suite. We stayed it this last year and it worked out much better for our family. I was able to get this suite for us for around $1800 total for our trip. We decided to go ahead and pay for this out of pocket. I booked a refundable room just in case something changes.

Third - Car Rental

Last but not least sometimes this is way higher than expected is the rental car. I immediately book the rental car no matter how crazy the price is on Costco. You can cancel without penalty if it goes down but it could go up. Currently, I have one booked for $600 but when I checked this week it was up to $700. I will keep checking it and hopefully get it down further.