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3 Credit Cards That Paid for My Family’s Trip to Hawaii

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If you want to take your family to Hawaii, here are the credit cards I used to earn most of those miles and points for the trip

Recently, I returned from a wonderful 10-day trip with my family of five to Hawaii. 

I did the math sitting on our balcony at the Hilton Waikaloa Village and figured our trip would have cost about $15,000 if we had paid the list price for everything. However, we only spent about $1,500, most of which were expensive resort-priced meals and adult beverages. 

Here’s a look at how we pulled it all together and the credit cards that paid our way.

Hawaii Is A Wonderful And Expensive Destination

The last time I went to Hawaii, I was 7 years old. My dad took us on a trip to Hawaii that included stops on both the Big Island and Maui.But my family never returned due to the cost and distance, and I hadn’t been back on my own.

Thanks to our Southwest Companion Passes, my two oldest kids fly free when my wife and I travel. Our third is a lap child. That means we only paid $5.60 per person each way in fees plus miles. For my wife and I, we found flights for about 60,000 Southwest miles total round-trip.

I picked two hotels to get some variety over our 10-day visit. Our first hotel was the Hilton Waikaloa Village Resort. I stayed at the same place back when I was seven. I loved the memories so much as a child that I made a point to return with my family.

The Hilton Waikaloa Village Resort didn’t disappoint. We enjoyed the most incredible hotel suite of my entire life, dolphins, sea turtles, a luau and an overall wonderful time.

Our second stop was the Sheraton Kona Resort & Spa at Keauhou Bay. The Sheraton was a lot smaller, and we ran into a handful of minor issues so I can’t give it as glowing of a review. However, we enjoyed the stay there, notably the pool, wild goats and evening views of manta rays.

The 3 Cards That Paid For My Hawaii Trip

If you want to take your family to Hawaii for 90% off like I did, here are the credit cards I used to earn most of those miles and points for the trip.

The Platinum Card® from American Express

We used the points we earned on our Amex Platinum card to book a huge chunk of our hotel accommodations. That’s because Amex Membership Rewards points can be transferred to both Hilton and Marriott. 

Not only that, but this Amex card gave us complimentary Hilton and Marriott gold status, which entitled us to perks at both hotels on this trip, including free breakfast at the Hilton. It also comes with another Priority Pass membership to take my whole family of five into a lounge without extra fees. 

How to Use and Transfer Your Amex Points

You can redeem your Membership Rewards to pay for all or part of your next trip using American Express Travel Online. Here’s how booking with points works.

Booking with Amex points

  • Visit the Amex travel portal site: Sign-in using your credit card account log-in details
  • Look for your desired travel options: Just as you would with any other online booking site, search for flights and lodging
  • Select the option to use Amex Membership Rewards instead of dollars: When you find the flight, hotel, vacation rental or rental car option you’re interested in booking, choose “pay with points”
  • Book with points and cash: Additionally, at check out, you can select the option pay with some of your points and the rest of the balance with cash
  • Book your travel: Membership Rewards points will be deducted from your total point balance once you confirm your purchase

Transferring your Amex points

If you have an Amex card that allows you to transfer Membership Rewards points to a frequent flier or hotel loyalty program, here’s how to do so.

  • You must first connect your Membership Rewards account to an eligible travel loyalty program: You’ll need your airline or hotel reward program membership number. If you do not see your desired loyalty program in the list of options, then it is likely not yet partnered with American Express Travel
  • Transfer your points: Select the option to “transfer points” to your desired airline or hotel and then confirm
  • Enter the amount of points you wish to transfer: Keep in mind that you need to transfer points in increments of 1,000 points. For example, you can transfer 2,000 points but not 2,500 points
  • You may pay a fee: Amex charges a per-point fee when transferring points to U.S. airlines. The fee is $0.0006 per point for a maximum of $99. You can roll this cost into the transaction and pay with points, or pay with cash or credit
  • Complete the transaction: Simply select “confirm and transfer” to finalize your point transfer. In some cases, the transfer is immediate, or it can take several days to complete

Chase Sapphire Reserve®

My longtime standby credit card is the Chase Sapphire Reserve. Right now, the Chase Sapphire Reserve starts you out with a generous sign-up bonus (enough for my family’s flights to Hawaii) after meeting the offer terms. 

We transferred 60,000 Chase Ultimate Rewards points to Southwest to book our flights. 

You also earn accelerated awards for every dollar you spend on dining (including eligible delivery) and travel purchases, and points on all other spending.

We use this card for any travel purchases that are not covered by miles or points and dining purchases to get the biggest possible bonus. I also rest easier knowing my trips are covered by the excellent travel insurance benefits of the card. I’m such a fan of this travel credit card, I even helped my mom apply for the Sapphire Reserve.

Chase Freedom Unlimited® Card

The Chase Freedom Unlimited is a cash-back card with no annual fee, but it comes with a superpower when paired with any Chase Ultimate Rewards card. You can turn cash rewards into Ultimate Rewards points at a rate of 1 cent = 1 point.

That means the Freedom Unlimited card gives us an equivalent of 5x points on travel purchased through Ultimate Rewards, 3x on dining and drugstores and 1.5x everywhere else. Right now, it has a valuable sign-up bonus for new cardholders that could get many households well on their way to a free vacation.

When using those cards regularly, you can see how the points add up fast. We use Freedom Unlimited as our “everything else” card in addition to the bonus categories.

Pro Tip: If you also carry the Chase Freedom Flex℠ Card, you can earn up to 5x on popular purchase categories that rotate every three months. If you use all three credit cards, you’re earning maximum Chase Ultimate Rewards points.

Never Pay Full Price to Travel

I discovered the world of miles and points about a decade ago, and it has been a truly fantastic ride. I’ve flown and stayed all over the world at a fraction of the typical cost. That’s a win for my lifestyle and my budget. But none of it would be possible without these rewards credit cards.

As long as you pay off the balance in full every month and avoid certain fee-bearing activities, you’ll never pay more than the annual fee. Once you earn your first big signup bonuses, your biggest problem will be choosing where to travel next!

While we work hard on our research, we do not always provide a complete listing of all available offers from credit-card companies and banks. And because offers can change, we cannot guarantee that our information will always be up to date, so we encourage you to verify all the terms and conditions of any financial product before you apply.

Eric Rosenberg
Eric Rosenberg
Eric Rosenberg is a finance, travel, and technology writer in Ventura, California. He is a former bank manager and corporate finance and accounting professional who left his day job in 2016 to take his online side hustle full-time. He has in depth experience writing about banking, credit cards, investing, business, and other financial topics. When away from the keyboard, Eric enjoys exploring the world and spending time with his wife and little girls. You can connect with him at Personal Profitability or EricRosenberg.com.