Home > Travel > Luxury Trip For 3 To Hawaii For $500

Luxury Trip For 3 To Hawaii For $500

Stay free in Kauai



The first time I went to Hawaii, I was a young pup just out of school. At that time of my life, sleeping on a floor surrounded by 5 other people was no big deal. Needless to say, it wasn’t a luxury trip. The second time I went to Hawaii, Jim and I had only been married a couple of years and we were in the process of running up $30,000 in credit card debt. We put the whole trip on credit and probably spent around $5000. My third trip to Hawaii will happen this summer. Our family of three is leaving the mountains for the ocean, and we are going luxury all the way. Since we don’t do credit card debt anymore, and we are now very careful with our money, how are we going to hula our way across the Pacific on the cheap? Miles and points, my new favorite currency! We are taking a luxury trip to Hawaii for just over $500.

As a disclaimer, I know many of my readers don’t use credit cards because of bad experiences in the past or because they are trying to shovel their way out of debt. I get it. You don’t have to read this post, but I hope you will because it shows that with some planning, smart spending, and patience, a family can take a dream trip to almost anywhere with very little money.

Airfare to Hawaii

For us and for most travelers, the airfare is the toughest part to tackle with points and miles. We had to have three tickets. Your family might need even more seats than that. The first step is to decide when ย you want to go and where you want to leave from. The more points you need, the longer you have to plan. For this trip, it’s taken over a year of planning to secure the amount of points to travel for almost free.

We knew we wanted to fly Hawaiian airlines. They give you a meal in coach, and we really liked their service the last time we flew to Hawaii. Jim and I both got a Hawaiian Miles Visa personal card, and I signed up for a business version as well. After we met our spending bonuses by putting all of our monthly expenses and business expenses on these cards, we had almost enough miles for 3 round trip tickets on Hawaiian from Las Vegas to Kauai. We were short 5,000 miles but were able to buy those for $73.90. Each award ticket costs $10 to book, so for our airfare to Kauai, we paid $103.90. Tickets are pricing out right now at $880 each, so I much prefer $103 to $2600!

The Hawaiian Airlines credit card has had a makeover and is now available from Barclay. It gives you 35,000 miles after spending $1000 on the card within the first 90 days, enough for a round trip ticket to Hawaii!


My taste in lodging has increased substantially since my first trip to Hawaii. I wanted us to stay in very nice places with big rooms. I was hoping to stay on the south side of the island for a few days, then move to the north side. I was also hoping for a kitchen and washer/dryer for at least part of the stay. With that in mind I read a million travel blog posts and decided that Hyatt and Starwood properties were our best bet. Over the course of our year of planning, I got two Chase Ink Bold cards, one for my optometry practice and one for Eyes on the Dollar. If you spend $5000 within 3 months, you receive 50,000 Chase Ultimate Reward Points that can be transferred to Hyatt to book free rooms.

That seems like a lot of money, but I had lots of business expenses with my practice that made the spending no problem. There are also some easy ways to meet a spending bonus, like sending your spouse money through Amazon Payments. For an average family like ours, if you put groceries, auto gas, electric bill, gas bill, car insurance, car maintenance, life insurance, cell phone, and internet on your credit card, that should easily be $1000 or more a month for expenses you would be paying anyway. Why not get free travel for paying your bills?

After that, we got a Starwood Preferred American Express card. We had to spend $5000 to get a 30,000 point bonus, but it was spread over 6 months, so that wasn’t hard. It does get annoying to have to call all the vendors and change billing methods every few months, but it’s well worth it in my opinion.



With those points banked, we booked 5 nights at the Grand Hyatt Kauai, which is fortunate because they have since raised the number of points needed to book free rooms at this hotel. We also booked two nights at the Westin Princeville Ocean Resort Villas with our Starwood points. We were a little short on having enough points for two free nights at the Westin, so one night was booked with points + cash. Our total lodging cost in Hawaii will be $180. Rooms like the one we reserved at the Hyatt are now booking for $705 per night, and the Westin is booking for $370 a night. Again, I like my $180 instead of paying $4265. Actually, if we didn’t have points, we would not be staying is such nice hotels, but it’s fun to get to travel like royals when you get the chance.

Other Vacation Expenses

We will have some other expenses for this trip. We’ll have to drive to Las Vegas, which takes about 8 hours, so there will be gas plus a night or two there. Luckily, week nights in July are not peak season in Vegas, so you can find really cheap rooms. We will get a rental car in Hawaii, and well, we like to eat. I haven’t decided yet if we will pay out of pocket for the Vegas room and rental car. We have some cards that offer travel reimbursement if we decided to use those for this trip. We also save all of our “silly money.” That’s what we call money received from non-working things like birthdays, taking surveys, or selling old stuff at the consignment store. We ย also save our change in a big jar and cash it in once a year for vacation. All in all we have about $1000 in our silly money fund that we plan to use for food or other things we might want to do on vacation. If we eat breakfast and lunch from the grocery store and limit our eating out to one meal a day, we should be able afford food and activities with our silly money.

Annual Fees

What about the fees on those credit cards? I know, I hate them too, but if the reward is worth more than the annual fee, I don’t have a problem paying it. For the credit cards we used for points, all the Hawaiian cards had a $75 fee that was not waived for the first year. The Starwood and Chase cards all waive their annual fee for the first year. When it’s time to pay the annual fee, we’ll look at the value of the card and determine if we want to keep or cancel them.

Total Cost For Hawaii

Our seven night trip to Kauai is costing $508.90 for airfare and hotels when you add in the 3 annual fees on the Hawaiian Miles credit cards. ย Considering this is an almost $7000 trip, I’m as stoked as an Olympic snowboarder!

Anyone Can Travel Luxury For Cheap

If you like the idea of traveling in style, you can do it too. You need to first pay off all of your consumer debt and obtain a great credit score. Put all of your monthly spending that you can on a rewards credit card and make sure you always, always pay off your credit card balances in full each month. Interest negates any sort of bonus reward. I am already planning a 2015 trip to Europe. I’d love to hear about your travel plans!


About Kim Parr

Kim Parr is a private practice optometrist, freelance writer, and personal financial blogger. You can follow her journey to 20/20 financial vision at Eyes on the Dollar.


  1. Holy cow- that’s awesome Kim! Seriously strong work on the rewards points usage! We are just beginning to do this more- we just got a Barclaycard Arrival World MC this year. I am looking forward to being able to write awesome posts like this as well some day!

  2. Very cool Kim! We’re planning a trip to Disney this year with the kiddos and likely looking at Europe in 2015 as well. Thankfully we have the airfare covered for Disney through my Mom as she is flying us all out for a cruise, so we need to earn points to stay at Disney and for the tickets in…which is basically a small fortune anyway. ๐Ÿ˜‰

    • You could probably put on of them through college for what tickets cost for 5 to Disney! I can’t wait to hear how you do it.

  3. Looks like travel and travel rewards is a popular topic this morning ๐Ÿ˜‰ The airfare is a killer for Hawaii so it’s awesome you were able to save so much. Actually, not just the airfare but also the hotels, so it’s great that you were able to get that covered/discounted as well. I would love to go to Hawaii again sometime soon!

    • I’m really sad to say how much we spent the last time we were there, but this is a whole different ball game. Airfare is terribly expensive, to anywhere. I’m so glad we were able to book the tickets we got and make the best use of the miles. It’s a bit of a crap shoot when you’re earning because you never really know if there will be availability when you finally get the points.

  4. I love this post. We went to Kauai in 2012 and we wanted to stay at the Grand Hyatt but the price was too much for us so we stayed at the Sheraton a few hotels down instead. I’m starting to get more into travel hacking so this post is exciting! ๐Ÿ™‚

    • I think the Sheraton is very nice too. We would have used our Starwood points there but wanted to stay on the north side for part of the trip.

  5. Kim, this is awesome!! This means that, theoretically, we could take our fam of six to Hawaii for $1000. Woohoo!!! Thanks for sharing the details on this. ๐Ÿ™‚

    • Six tickets would be daunting, but I know Jake at I Heart Budgets did a churn for six or seven to Hawaii. It’s totally doable if you plan long enough.

  6. That is impressive Kim! A Hawaii trip is very expensive. I had heard that before we went but was surprised at the price of gas, food, excursions, etc. I’d be interested to know how much you spend over a week with things like that. A follow-up post idea perhaps?

    • Yes, I will certainly do a post trip report. Gas is pretty unavoidable as we’d like to explore the island. Food will be more expensive than home for sure. If we stick to beaches and hikes, it will be cheap for excursions, but I kind of want to do this float trip that is pretty expensive. We’ll see.

  7. WOW! You guys really beat the system! I’m impressed. I was looking at going to Hawaii but wrote it off as being way too expensive. Perhaps I should re-evaluate a good credit card strategy …. ๐Ÿ™‚

    • MMD, there are lots of people that can help you. I know a little bit about churning, but there is so much to learn. I think if you plan for a year or even two, you can take any trip you want paid for mostly by points. We are staying in really, really nice places, but there are tons of places that don’t need so many points that would be just fine for a family trip. We just wanted this one to be really swanky in the hotel department.

  8. Wow! Way to rock the bonus points!! I’m amazed. I would love to stay at one of those swanky places ๐Ÿ™‚

    When we went to Hawaii a few years ago, we stayed in a condo and cooked our own food. It was pretty awesome, but one night we went to Wolfgang Puck’s restaurant, saw how the other tourists were staying, and got a bit jealous ๐Ÿ™‚

    • When we went on credit, we stayed in a really nice place. It was awesome, but I’d never pay retail for something like that again, even if I was rolling in money.

  9. I love Hawaii! When the girls were quite young that was where we took our annual vacation. Just so beautiful and relaxing. ๐Ÿ™‚ I’m sure your daughter will love it too. It’ AMAZING that you were able to get such great deals with your credit card churning. And it is especially nice when you are treated like royalty but only paid pauper prices.

  10. Sounds like you guys will have an awesome trip. My wife and I went to Hawaii after we got married…our favorite vacation so far. Kind of a long flight though from the east coast. We’d definitely like to go again…but with a little baby, we probably won’t be traveling much in the near future. I regret not getting into credit card churning earlier and hope it’s still available in the future.

    • I would have never done a flight over 3 hours with a baby. Too stressful. I think around 3 or 4 is when we started traveling a bit again. I think credit cards are always going to try to entice you in with something, but I can see the minimum spend to get the bonus going up.

  11. Wow awesome job Kim!! I really want to get to Croatia/Slovenia next year so I should really start planning now with maximizing credit card points. I think this year will pretty much be taken care of with the exception of hotel at fincon. If I can’t get a roommate I honestly probably won’t go. Just too expensive otherwise.

    • Airline tickets to New Orleans always seemed expensive to me. Not sure why. I’ve heard Croatia is beautiful and isn’t it pretty cheap compared to US dollar?

  12. Dang! Everyone seems to be getting all these amazing credit card rewards at the moment. Wish we had opportunities like these in NZ.

  13. I used to also get caught up in credit card fees. Now I’m with you: if the benefits outweigh the fee significantly, who cares?

  14. Nice work Kim. I think you are doing well with using points and miles. I am hoping to pay for a few trips this year with a little bit of churning. Your post just gets me excited about doing so.

  15. Yeah, that price tag ought to have you super stoked dude. Nicely done. I have been to Kauai twice and loved it both times. Do the helicopter ride through the Napali coast if you can, amazing!

  16. KimKim
    Kauai is the nicest island. If you’re there on a Friday night and like crab legs the Marriott in Lihue has the best crab leg buffett. Well worth it. Hamura salmon is another must eat

  17. Thanks to credit card points & miles, we booked a free flight to Japan this summer (well, we had to pay $40/person for flights that normally would have cost at least $1,300 RT/person). On the other hand, I had a scare with my credit score/report that has since been cleared up, so that makes me a little wary of having all these credit cards and doing the frequent applications. Maybe we’ll have one credit card application this year, but that’s it.

  18. Great post!! We are just getting into travel hacking, but it’s clear you can do some amazing things if you are organized and have a goal in mind! Thanks for sharing your story ๐Ÿ™‚

Leave a Reply

Your email address will not be published. Required fields are marked *


This site uses Akismet to reduce spam. Learn how your comment data is processed.