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  • Writer's pictureMr. FI Musician

How We Booked a Two Week Trip to Hawaii for Free

Back in 2016, when Mrs. FIM and I were planning our wedding, we decided to have a destination ceremony. With Mrs. FIM's family living in Europe, we knew our families weren't going to be spending much time together after our wedding was over, so we chose to make a vacation out of it. We Airbnb'd a villa in Cancun for five or six days that was big enough for both of our families.


We didn't want to ask our families to spend thousands on plane tickets and housing, so we made a commitment to pay for everyone's flights as well as the full price of the Airbnb. It came out to about $10,000 to get all 11 of us to Cancun. In addition to setting aside as much income as we could from our gigs, I drove Uber & Lyft for a year and a half. We somehow managed to save up enough for the trip.


But wait, I thought you said this post was about Hawaii?


Yep, I'm getting there.


Once we had enough saved up for the flights, I signed up for the United Explorer Credit Card. I knew we would all be flying United, and I figured I'd use the massive amount of money we were spending to get bonus miles. I believe at the time we signed up, we received 60,000 bonus miles if we spent $3,000 in the first three months.


$3,000 in three months? No problem. I've been saving for this for over a year!


So we got our 60,000 bonus miles, plus several thousand more for actually flying to Cancun. We decided to hang onto the card and continue to rack up miles to use for our honeymoon someday. The card has a $95 annual fee after the first year, but we decided it was worth paying because United gives you a free checked bag on all United flights. Knowing that Mrs. FIM would be traveling to Europe at least once a year to visit family, we knew we would recoup that fee easily by saving on baggage with one round-trip.


Flash forward almost three years later to late 2019. We had been using our United card on all of our regular purchases and paying it off in-full each pay period. By doing this, we racked up over 125,000 points. Our goal: Use the points to cover our flights for a honeymoon to Hawaii.


We finally had enough points to book a 10-day trip to two islands. But by this point, we had gotten deep into the FI movement and decided we wanted to also get the hotel rooms covered.


The day after Christmas I spent around six hours researching hotels in Hawaii, the number of points needed to get a free night, and how many signup bonus points credit card companies were offering. I eventually found a way for us to get ten days of hotel rooms covered, all through Hilton Honors cards.


First, I signed up for the American Express Hilton Surpass Card. This gave us 150,000 points for spending $3,000 in the first three months. Once we hit that number, I signed up for the American Express Hilton Honors Card. This one gave us 75,000 points for spending $1,000 in the first three months. Finally, Mrs. FIM also signed up for the Hilton Surpass Card, which gave us another 150,000 for spending $3,000 in three months.


Okay, so we needed to spend $7,000 total to get 375,000 points. I need to make a few important points about this.



First, we only signed up for a new card after we hit the bonus on the previous card. Since we only had a certain amount of time to get the bonuses, we wanted to work on only one at a time. As soon as we spent the amount needed to receive the bonus, we stopped using that card and replaced it with the next.


Second, we did not make each other authorized users on our cards. If I had made Mrs. FIM an authorized user on my Hilton Surpass Card, she would not have been eligible to receive the signup bonus for her Surpass Card. Because of this, we kept our cards separate from each other. It's very important to read the fine print about who is eligible for bonuses.


Third, we had a few larger expenses coming up for which we had been saving up. Mrs. FIM needed to get her flute fixed up, I was long overdue to order cases for my marimba. We waited to purchase these items until we had the cash available to pay them off immediately. We used our cards to make the payment then used cash to pay off our credit card bill in full.


You should never sign up for a credit card with the idea of getting bonus points unless you can pay off your card in full each pay period.


Let me repeat that.


You should never sign up for a credit card with the idea of getting bonus points unless you can pay off your card in full each pay period. The interest rate is so high that the money you spend paying the interest negates the bonus points you receive. If you don't have the cash to pay off your bills, don't do this!


So between large ticket items we had been saving for and our day-to-day expenses, we were able to hit the spend amounts for all of the cards.


Then I got to work.


...to get a free trip to Hawaii.


I used the Hilton points to get our hotels booked and the United miles to get our flights covered. I was shocked at how easy it was. Within an hour we had everything set. Ten days in Hawaii!


But wait...this article is titled 'How We Booked a Two Week Trip to Hawaii for Free".


Yup. We booked the trip in early March of 2020. We all know what happened two weeks later.



Two weeks later I called United and Hilton and cancelled everything. Luckily we were able to get all of our points refunded.


In the meantime, we decided to rack up more points. We both signed up for the Chase Sapphire Preferred Card which gave us each 60,000 points by spending $4,000 in the first 3 months. Again, we did this one at a time, not simultaneously.


As vaccines rolled out this year and things started to look optimistic, we decided to rebook our honeymoon trip for April 2022, four years and eleven months after our wedding. Never too late, right?


The good news is that we had way more points than last time. I was able to transfer some of our Chase points to United and book flights to three islands over fourteen days. Our Hilton points got us fourteen nights in three different hotels. We used leftover Chase points to cover car rentals on all three islands.


We still have approximately 25,000 Chase points left over and we have six months to build up additional points. Depending on where we're at in early spring 2022, we may elect to use our Chase points to get cash back so that we can cover food and other expenses while we are in Hawaii. In the meantime, we are satisfied over the fact that a trip that would have been over $7,000 cost us $0.


The Takeaway

A few years ago I remember a few of my friends hyping credit card signup bonuses. I also remember dismissing them as chumps who were obviously being scammed.


I was wrong. Credit cards can be a very effective way to get free shit. You just need to be smart and careful. Don't assume things and take the time to research and read fine print.


So if you've been dismissive about credit cards, it might be worth doing some research. If you can handle them responsibly, they can be well worth the bonus points earned.


Just make sure you have the cash to pay off your bill each month!


In my next post, I'll be sharing a story about an added bonus we received when we booked our hotels with Hilton: Free nights in Vegas.


Have you taken advantage of credit card signup bonuses? If so, share your experience in the comments below!

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