Can you tell us a little about yourself?
My name is Daniel. I make websites and apps from a computer which is mostly located in Chicago, IL, USA. I can work from anywhere with an internet connection, so I originally gained an interest in using airline miles as a way to live and work from new places. That hasn’t totally happened yet, but I have been able to book some vacations instead!
Can you tell us a little about your most recent trip that you used points to go on?
My most recent trip where I used points was last fall. My ex-girlfriend had just been offered a new job, so we decided to take a very last-minute trip abroad. She’d recently received her sommelier certification, so we chose Valle de Guadalupe in Baja California, Mexico. It’s essentially Mexico’s version of Napa/Sonoma wine country, since the climate is very similar.
All of our flights, our rental car, and both hotels were all paid for with credit card points. We flew from Chicago to San Diego, where we rented a car to drive across the border.
Once we were in Valle de Guadalupe, we had booked a cheaper mid-range hotel for the first three nights called Hotel Boutique (yes, that’s really the name). Then we decided to splurge with our points for the last two nights at Encuentro Guadalupe, which is a sort of eco-resort. The rooms are these very cool boxes scattered across the hillside, with amazing views of the valley and vineyards.
What made it a great trip?
The region was incredibly friendly, and everybody was excited to show off their wine. We went during the week and most of the wineries were totally empty. Occasionally the wine was great, but for the most part it was just interesting or unusual.
It felt like a beautiful mix of Mexico, Northern California, and Italy. Everything was beautiful. Most of the must-sees are the vineyards themselves. Our favorites were Cuatro Cuatros, Vena Cava, Bruma, and Bichi. That said, there were so many where we had a nice time.
How did you use miles to pay for the trip?
My primary method is to put the majority of my regular spending on a Chase Sapphire Reserve card. The yearly fee is expensive, but worth it for how I use it. I go to a lot of restaurants and bars, so the 3x points adds up. Plus we redeemed our flights, hotels, and rental car through the Chase portal which meant we got 1.5x spending power.
I also used RewardStack throughout the year to make sure I got all the points I could. So when I bought a new laptop from Apple, for example, RewardStack was there to make sure I got the points.
In the future I’d like to get a little more sophisticated with my points collection, but I’d also just like RewardStack to keep getting better so that I don’t have to spend too much time thinking about points. I’m more interested in the trips!
What’s your next trip that you’re planning to go with points?
I’m about to live+work from Europe and South America for the next few months. Not sure how I’m going to use them yet, but having points in my pocket ready to spend is how I want to live.