How To Travel For Free: A Free Trip To Hawaii For 7 People

*This post may contain affiliate links, please see my disclosure

December marks our one-year anniversary on our adventure earning tons of credit card travel rewards. It started out with a simple goal;

One free family vacation every year.

I had read about people traveling around the world on rewards points and such, but it sounded too complicated and elaborate for normal folk such as ourselves to ever get any benefit out of it. We decided to make the leap in December 2012 and have taken 3 trips since then, all paid for with credit card rewards.

So for booking our last trip of the year, I decided to step it up a notch and try to get our family to Hawaii for free (specifically, Maui). We have pulled everything together now, and I am booking 7 plane tickets today. We’re also getting two rentals cars for free, and now working on having most of the food covered for 10 days.

That’s $5,000 of this trip paid for through credit card rewards.

Update: This post has been updated in 2020 to show you the BEST way to get your family to Hawaii for Free!

Airline Credit Card Rewards For Our Free Trip To Hawaii

When I started researching flights to Hawaii, I was disappointed, as they cost anywhere from 40k  – 60k miles for a single person, round trip. UGH. Since most credit cards max out their bonuses at 50k or so, I didn’t think we were going to be able to get free flights all around.

We had 6 adults, and toddler (over 2 years old), and a baby (under 2). Luckily, 2 and under can be a “lap infant”, so no ticket required, but we still needed enough rewards to cover 7 tickets.

The other problem was only 3 of the 7 people could get credit cards to earn the rewards. So it was looking like we needed 300,000 miles just for the tickets on 3 credit cards. But then I found a sweet loophole.

British Airways rewards are wonderful, in that they can transfer to Alaska or American Airlines. They also do something called “distance based awards travel”, which means using their miles for shorter flights costs less point. And since we’re on the west coast, that means we’re closer to Hawaii than most others!

Using this handy dandy tool, I found that using British Airways miles through Alaska Airlines means we can get a round trip flight to Hawaii for only 26,000 miles!

For a limited time, the Chase British Airways Visa Signature credit card comes with a LARGE bonus offer, so we signed all 3 of us up for the card. That means we just earned 6 round trip tickets to Hawaii on only 3 credit cards! BOOYAH!

And since we need 7 tickets, I was able to transfer the extra miles needed from my Chase Ultimate Rewards account. We needed about 10,000 miles extra to book the 7th tickets, so I just hopped over to the Chase Ultimate Rewards portal and made a quick transfer to British Airways. Done and done.

So then all I had to do was look for Alaska Airline “Super Saver” tickets to Hawaii, or the ones that cost 20k miles each way. They sell out quickly, so we are booking our vacation about 11 months out. Here’s what it looks like on the Alaska Air website.

Alaska Air To Hawaii

After I find the flights, I just need to give British Airways a phone call, give them the flight details, and have them book the flight! The do charge a $30 “processing fee” to book over the phone, but for this deal, there’s no way to book it online. We’ll happily fork over the $210 in fees to book $3,500 worth of flights for free.

Free Car Rental On Credit Card Rewards

Now that the flights are taken care of, we want to rent two cars for the families to venture our way around the island. We’ll have two kids, and 6 adults, so we’re going to rent two sedans to cram us all into.

The BEST site for Hawaii car rentals, hands-down, is http://www.discounthawaiicarrental.com/. Even in 2020, you can get a Mini-Van for a WEEK for under $400. CRAZY!

I have also rented a few cars this year for several short trips, and have found the best deals at Dollar. They seem to consistently have the lowest price by a decent margin, and brought our rentals down to about $20 a day or less.

Another place I also suggest checking out is Autoslash.com. If you book early, they constantly search for better deals, and if they find one, they automatically rebook your car rental and save you money. This can happen several times and save you a bundle.

Since we’re going to be booking on one of those sites, we needed a card that didn’t use rewards to book, but that gave us cash back or an equivalent.

Enter: The CapitalOne® Venture Rewards card

This card is perfect, because it offers a generous sign up bonus, and you can use it to erase travel expenses. The points are worth $.01 per point, for example: 50,000 points  = $500 in travel rewards.

Check out the latest welcome bonus offer on this card HERE

The way it works is to simply book whatever travel you are doing (flights, hotels, rentals cars, etc.), and then you apply your rewards towards those purchases as a statement credit.

We’ll be in Hawaii for 10 days, which means if we can average $20 a day for each car, that will total $400 in car rental fees. So one of these cards should erase that expense completely. DONE!

Pay For Food With Credit Card Rewards

For this, we’ll need a good cash back rewards card. I chose the Chase Sapphire Preferred card. The points are more versatile, and can be converted to cash, or transferred to a partner hotel or airline.

In this instance, we’ll choose the cash back option, and should have $450-$500 for food available from one cardholder. If we get another person to sign up, that’s close to $1,000 for food.

Since we’ll be in a beach-front condo, we can shop and get most of our food to eat in. $1,000 should cover 10 days, and any eating out we’ll just cover it on our own.

But, Where Are You Staying?

In Hawaii with 7 people, it’s much more economical to go to VBRO or AirBnB and find a good condo to rent out. Our family is pooling together our Christmas and birthday money for 2 years and booking a beach-front condo for 10 nights.

We have found deals for $2,000 – $2,500 for the ten night stay. We may offset this with some more cash back cards, but it’s still an incredible deal.

Can Real People Do This?

Here’s the deal. I have tried to convince many people to join us in our venture of getting credit card companies to pay for their next vacation. Most just laugh and find an excuse why it wouldn’t work for them. But after this vacation, I know people are going to start asking questions. And the first question is “how can regular people do this?”

Honestly, it’s very simple.

  1. Have a decent credit score (700+).
  2. Check out the BEST Travel Rewards Cards, sign up for cards and earn rewards.
  3. Use the rewards to book flights, hotels, rentals, etc.
  4. Have a fruity drink on a warm, sunny beach.

If you think your travel plans may be too complicated, feel free to send me an email for my next Travel Rewards Case Study, and I’ll see if I can get you your next free vacation.

Comments: Have you used rewards points to travel for free? What are your favorite ways to earn miles/points? Anyone here used the tricks above to get to Hawaii?

Jacob Wade

Jacob Wade

Jacob Wade has been a nationally-recognized personal finance expert for the past decade. He has written professionally for The Balance, The Spruce, LendingTree, Investing Answers, and other widely-followed sites. 
He’s also been a featured expert on CBS News, MSN Money, Forbes, Nasdaq, Yahoo! Finance, Go Banking Rates, and AOL Finance.

In 2018, Jacob quit his job and his family decided to sell everything (including their home) to take off on an adventure. They traveled the country in an RV for nearly 3 years, visiting over 38 states, 20+ national parks and eventually settling in the sunshine state!

67 thoughts on “How To Travel For Free: A Free Trip To Hawaii For 7 People”

    • Thanks FI. We did cash-only for a few years, but have enjoyed reaping the rewards this year. As long as our spending is in check, figure we might as well get some free travel out of it 🙂

    • Join the dark side Mr Pilgrim! 🙂

      As long as you don’t buy anything you wouldn’t have anyway, and set up an automatic payment to pay the balance you’re golden.

      @Jacob – this is extremely impressive. I went for cash back this year and have amassed around £400/$650 over two cards. I think the travel cards pay better bonuses so I will look into this in the new year!

  1. West coast to Hawaii is one of the sweet spots for Avios (the other being a couple east coast places to a couple places in Europe)… great job!

    I think you were smart to use a vacation rental. Trying to get enough points for 7 people in a hotels would have been a major PITA.

  2. I’d still give it a year after paying off the cards, as you’ll need to establish a financial foundation for life without CC debt. We did 18 months of cash-only before jumping into CC rewards when we first got married, and it was great.

    but once you’re rocking a steady budget, definitely jump on this 🙂

  3. Definitely looking for tips. We want to go all out, excursions, luau and all. Looking to do it on the cheap, of course, so any tips are appreciated.

    Feel free to shoot me a mail: iheartbudgets :at: gmail :dot: com

  4. I “engineered” a trip to Hawaii for the family last memorial day where I got tickets for $125 in F roundtrip. Unfortunately, life happened and we had to eat the cost. We were going to Maui as well [….] have fun for me 🙁

    There was a hike I did a while ago where you hike back to like 7 waterfalls. It was on the Rd to Hana and super worth the day to pack a picnic and head back there. Have fun!

    • Bummer. $125 in F is a crazy good deal. We’ve been sticking with coach to get more out of our miles, but our NYC trip will most definitely be first class 🙂

      I think I know the hike you are speaking of, definitely plan on that one as well. I’ll have a Mai Thai in your memory 😉

  5. That is seriously amazing. My issue is I can’t spend the minimums. If I could pay my student loans with a credit card (ha!) I could do it, but aside from my student loans, my spending on anything aside from that and rent is minimal. I couldn’t spend $1000 per month for budget reasons. Should I just wait till I am free of student loans? I LOVE traveling and don’t want to wait several years to do so, but the spending minimums get me. Rent, food, transportation, et al is about $700-800 for me.

    • Always prioritize paying down debt, but if you can put your regular budget on a rewards card and stick to a good spending plan, then go for it!

      The Barclaycard is $1,000 in 3 months, so you only need to put $334 a month on it. We put all utilities, bills and monthly spending in our cards. Basically, anything outside of mortgage and student loans 🙂

      That card also get’s 2x pts on every purchase. So you’d get the $400 bonus (40k pts), and then be earning 2x pts from there on out. Probably the best starter card out there currently 🙂

  6. When you told Vonnie and I how you were doing this at Fincon, my mouth dropped to the floor. I read this article, and it happened again. My personal issue is with self control of not continuing to spend and using those lines of credit. Maybe if I set a goal (like travel plans) I could do it. I do like a good challenge…..

    • I’d say that challenge can wait a year, you guys just rocked an AMAZING journey through massive debt payoff. Ride the wave of debt freedom, get on a steady plan for 12 months, and then weigh your options. We were cash-only for 18 months before jumping in. Helped us rock a sweet budget and built spending habits that are rock solid 🙂

  7. You may find a little hard booking 7 tickets on the same flight.

    It’s a pity using the cash back option on the Ink Bold Ultimate Reward points.

    Not bad for a personal finance blogger 😉

    Clear disclosures, thumbs up.

    For a little more “burn scale” you may want to check out my masterpiece trip report “Megatrip: Planes, Trains and Cows” under Trip Reports on my site.

    • Yeah, ran into the scheduling issue, but found some availability when we got a little creative. Flexible dates are VERY important when travel with 3+ people 🙂

      I apologize to all travel bloggers ahead of time for not getting 3+ CPM for my UR pts. But hey, it works for us 🙂

      And great read, thanks for the suggestion. You definitely have mastered “traveling in style”

    • Yea, we did my wife’s Barclay Arrival and we both have the Amex Blue. That’s paying for the Bellagio. The SW card is getting us there.

      For Disney, we’ll likely both start with the Chase Bold Ink (or Ink Bold?) and go from there.

      With Europe, I’m not so sure yet. There is a Lufthansa card that gets you a ticket with points and a companion, so that could be a possibility for getting there.

      • Sweet! Word of advice, once you go Ink, you never go back. We’re rocking an average of 3x pts on every purchase, and have all our bills and utilities on it. The rewards stack up fast!

        I think we’ll do British Airways through a partner airline to Europe…not 100% sure yet.

  8. Impressed as always Jacob. The more I read about this the more I feel like I should be diving in. I kind of feel like one of those people who always says they know the “should be” investing but haven’t started yet. Maybe it’s time to take some of my own advice.

  9. Very cool. When I traveled to Hawaii I used Airbnb to find a sweet studio a block from the beach that cost less per day than my NY rent (shared w/two other people). Made me reevaluate my life choices…

  10. I love this so much. Jacob I think I’ve mentioned before (or maybe just in my brain, hehe) that I would love to do this for a future vacation. Last time the thought occurred to me, I was still pregnant with baby #3 and wasn’t willing to make ANY long-term plans until the baby was born, ya know?

    Well she’s here now and is almost 3 months old. Big kids are turning 3 and 5 this week. I think it’s time to think about a Disney World vacation in late 2014.

    We live in Indiana. Probably would consider driving down (even though that sounds kind of horrible and long), but all the car seats and crap might be a huge hassle for flying, plus renting a vehicle. So maybe we can just suck it up and drive? I dunno…maybe flying would be a worthwhile goal.

    Anyway, I would want to stay on an on-site hotel. Maybe something with a meal plan. I dunno. All of these thoughts are coming to me this morning so I will need to take a look.

    Before I pick my card to apply for, can I run it by you via email to get some feedback? Please and thank you 🙂

  11. Ok wait — maybe a flight would indeed be a worthwhile goal. I could have my big kids in small boosters and my baby might still fit in my bucket seat, so that’s easy enough. A flight would get us there way faster anyway, and we wouldn’t be road-weary for Disney. Hmm.

  12. Thats some seriously baller financial savings and CC manuevering! I think you’ve convinced me to go for it in 2014. We had given up CCs while getting out of debt and growing our wealth, but I think we’re in a good enough position now. Thanks for sharing!

    • As long as you’re rockin’ a sweet budget, you’ve got everything to gain. I’d start with the Barclaycard because of the easy minimum spend and redemption (all depends on your travel plans, tho), and then follow along for some more advanced, fun stuff as you get into it 🙂

  13. I’ve had success getting the booking fee waived when calling BA just by telling them that I tried booking online and the system was giving me errors. Might be worth a try if you haven’t already booked 🙂

  14. very fascinating! I have never tried this, but am going too. One of my co-workers does this and I was intrigued as she travels overseas everywhere for next to nothing!

  15. So, British Airlines didn’t charge any fees for the award tickets?
    I had looked into transferring Amex points to BA for an NYC-London flight and they were charging a few hundred for taxes, etc.

    • We booked BA through Alaska Airlines, so no fuel surcharges.

      But yes, booking on the phone, they wanted to charge $30 per person ($210), and I told them I tried booking online and it failed (it did). They then waived the full $210, and I was only charged $30 total in fees. 🙂

      • @Bill – there are several components to British Airways to Europe:

        1. Fuel Surcharges – for Flights on BA or AA, they charge fuel surcharges – and if you are looking at premium cabins, it is more than economy. The airlines to look at are Aer Lingus (only about $150), Iberia and Air Berlin. None of these fly direct to London.
        2. ADP – if you fly out of London, you will pay Air Passenger duty on those tickets. This can easily add $200 to an economy ticket. (Avoid flying out of London!)
        3. If you want to save points – look at transferring points to Virgin Atlantic. From JFK, 17,500 points & about $150 in fuel surcharges. This is for the outbound only! Otherwise, your might want to look at transferring points to Air Canada for use on United from EWR-LHR – the cash portion would be $2.50
        4. For the return – book a cheap flight to Dublin and then use BA Avios to book one way from DUB-JFK (20,000 points), or DUB/SNN- BOS (12,500) points.
        5. Aer Lingus is only available for redemption via the phone – not online. As always, double check that flights are available before you transfer your points.

        Your other option, would be to transfer to Delta and book Virgin Atlantic. Since Delta allows one stopover, I would look at add a few days in Paris or Amsterdam and leave from those cities back to the US.

        @Jacob – AS is not available as an online redemption for BA. You always have to call in for thos bookings – and usually they won’t waive the booking fee.

        • Thanks Katherine. Yes, usually you pay the booking fee, but I tried booking online, got an error, and then told them that on the phone. They had no problem waiving the fee. And even if i did pay fees, I’d use my Barclaycard to pay for it and have the charge written off with points 😉

  16. I am always amazed at how lucky Americans have got it when it comes to briiliant rewards programs and cheap holiday packages.

    Flights from Australia cost a fortune to go anywhere!

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  19. Fantastic tips! I am going to try definitely. At first I don`t believe my eyes but eventually you convinced me that this is possible. Thank you for sharing such a great idea! Best regards!

  20. Love your ideas! Do you cancel the credit cards after your vacation? I see that you are mostly using bonus sign up points. How would you use your credit cards to book this vacation a second time?


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