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  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  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.  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!



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Snipon is owned and run by a small team who love to find deals on a dime along with the best sweepstakes and giveaways out there. We’re always scrolling the internet for the latest offers to share them with our community. Sign up for our weekly newsletter so you don’t miss another freebie!
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