Post updated 6/18/24

We started dabbling in points and miles midway through 2021 and picked up the pace as we got into 2022. We’ve been collecting and redeeming credit card points for over three years, so I thought it would be fun to walk through all of the flights and hotels we booked in our first year in this hobby. When we first started doing this, I started to worry that we’d run out of bonuses for which we were eligible. I was quite mistaken – there is a whole community of points and miles experts out there who have been doing this for years and still have not run out of cards to open and rewards to earn.

In the beginning, all we really wanted to do was cut down on the cost for five people to fly to Disney. We opened the Chase Southwest Rapid Rewards card for a 40,000-point bonus. Tom understood much more quickly than I did that the Chase Sapphire and Chase Freedom were the next step. Soon we had over 100,000 Ultimate Rewards that could be transferred to Southwest with the potential to keep earning points with 5x on groceries, which was the introductory offer on the Freedom. We quickly had enough points to book our flights to Disney, and more left to book flights to Austin for my cousin’s wedding. The addiction began in earnest!

I won’t walk through all of the rest of our credit card openings – that would get long and boring – but here is a photo chronicle of what we redeemed in our first year:

Tom and I had a no-kid trip to Austin to attend my cousin’s wedding. We booked flights via Southwest for around 40,000 points and saved ourselves $600.

Next up were our five flights to Disney in January of 2022. We used around 95,000 Southwest points after transferring what we needed from Chase and saved around $1500. Photo of my family’s favorite Disney landmark.

Up next, in May 2022, was our first trip back to NYC since before the pandemic started. I was meeting my college roommates for a little reunion, so Tom decided to bring the kids and hang out with his brother and partner who live there. We used Marriott Bonvoy points to book three nights at the Courtyard Manhattan/Midtown East. This saved us around $1200. 

Next, for August, 2022, we booked two nights at the Courtyard Marriott Bayfront in Erie, PA, with this view from our room. The cash price at this hotel is always really high, but I always wanted to stay here. Overall, we liked the hotel, but it was super crowded, and the infinity pool looked way cooler on the website than in person. We used 2 free night certificates for this, saving us around $700.

After a couple of days swimming and hanging out on the beaches of Lake Erie, we traveled on to Niagara Falls where we stayed at the Embassy Suites Fallsview. We booked a suite with an amazing view via the Capital One portal (I had a period of obsession with this portal) and used points erase to save about $500 on this trip.

In January of 2023, we took a long weekend in the mountains of West Virginia where we were able to use the points eraser on our Capital One card. That’s the smile of a guy who didn’t have to pay for his lovely mountain cabin. Savings this weekend totaled around $750.

Finally, later in January, we did the silliest thing of all! We went back to Disney and stayed at the Walt Disney World Swan hotel for nearly free, just because we could. We loved this trip because the hotel had great pools, great food, was walking distance to our two favorite parks, and was included in some bougie Disney perks like early entry and late-night extended hours. We also used Chase Ultimate Rewards in combination with Southwest Rapid Rewards to book our flights. Savings here were $1500 for flights and $2800 for the two rooms we booked. 

All told, from November 2021 through January 2023, we were able to book roughly $9550 worth of travel. We’ve learned a lot along the way and are looking out for even better redemptions in the future. Since this first year of getting our feet wet, we’ve been able to travel to Colorado, Montreal, Charleston, France, Puerto Rico, Utah National Parks, and way more. Can’t wait to see what other adventures lie ahead!