Life is so much more interesting when you “game-ify” everything. Maybe I’m actually more competitive than I thought, because the idea of winning free travel gets me feral and sometimes teamwork is what wins the game. In Spring of 2023, my parents, brother, and I collaborated on a trip to Maui, Hawaii and our combined travel points made what normally would have been a crazy expensive trip into a manageable one.
If you have ever been to Hawaii, any island, you know how expensive it can be. Hotels are frequently $400+ a night and flights can be worse. If I would have paid out of pocket, my flight would have been close to $700 round trip. Unfortunately, I live in a region without any major airline hubs within quick driving distance so that was working against me. My family lives on the West coast so they had shorter and cheaper airfare.
As a solo traveler, it would have taken me a long time to accumulate enough points for flights and hotels for the whole stay. Luckily, it wasn’t just me! My mom covered the hotel using five free night certificates from a Marriott Bonvoy credit card sign up bonus (bonuses offerings change frequently) and we all chipped in cash for the car rental.
We stayed at the Residence Inn Wailea on south Maui. It’s technically a long term stay hotel more than a resort, but the vibe was still bougie and the pool was top notch. There was very little ocean view, but the grounds were beautiful and it was nice to have a small kitchen in the room. There are several other point-hackable hotels in Maui, but the Residence Inn fit our needs and free night-certificate limitations within our timeline.
The free night certificates were part of a limited-time sign up bonus for one of the Chase Marriott Bonvoy personal cards. Usually, I think they offer three nights instead of five. While they are officially called “free night certificates” there are several stipulations for using them. They only work for stays up to 50,000 bonvoy points per night, with the capability to “top off” with a max of 15,000 additional points per night. For example, our stay was 57,000 points for the weekdays and then Saturday was a bit higher but I don’t remember the exact number. So we had to use additional points on top of the certificates, but those were earned through regular spending while the bonus minimum was reached. We ended up staying six nights, so only one night was the cash rate of $450.
Already with just the hotel alone, we were saving around two grand by using points! I couldn’t wait to get there, but the flight prices from the closest big-ish airport were terrifying. Knowing I wanted to be able to afford my mortgage for the next few months but still go on this trip, I devised a plan to get to Maui on points as well.
There are ways to get to Hawaii for 15k points on Turkish airlines/united, however, the dates that those flights were available didn’t work for this trip. After looking at my options for airlines and seeing what card offers were available I decided to fly with American Airlines and I opened the City AAdvantage business card to earn 60k points after $4,000 minimum spend.
The business card had an annual fee, but I was 5/24 for chase cards and couldn’t open another chase card until one of those old cards reached the two year mark. This card was through Citi which is why I was able to get it. Also, business cards don’t count against the 5/24 rule with Chase so I was leaving my options open for future cards later this year.
The bonus wasn’t quite enough points to get me to Maui, so I had to top off my account another way. I could have transferred from a different card that partnered with American airlines, but I didn’t think of that at the time. Instead, I purchased 5k extra points for around $80. On the way to HI my seat was basic economy, but since the return flight was overnight, I splurged on the economy plus and got a seat that could actually recline. 10/10 would do again, it was worth the extra $80ish to get that stretch, normally I can’t sleep on planes. In fact, I stayed awake for an entire flight from Denver to Frankfurt because I couldn’t feel comfortable smooshed in between people in the multi-million dollar sardine can. The jetlag on that trip was horrible and I didn’t want a repeat.
Anyway, with a little bit of strategy, it is totally possible to hack your way to Hawaii and win at life. By booking my flight and hotel with points, my hard earned dollars were spent in more enjoyable ways, like a snorkeling trip, and dining at many delicious restaurants.