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12 Day Hawaii Vacation under $725

12 Day Hawaii Vacation under $725

12 Day Vacation in Hawaii on a $725 Budget

Last Fall, me and my girlfriend Leslie were sitting in the Hotel I was living in and came across a trio of airline tickets that would take us from Boston to Kauai, Kauai to Oahu, and finally Oahu back to Boston. The total for these tickets was $600. If you’re keeping track of the title then you may be wondering how I haven’t already busted my budget but it’s a simple thing called travel hacking.

Most insane rainbow I had ever seen on the west-side of Kauai

Three One-way flights and 12 days of rental car: $386

Travel hacking is just the act of using credit card or other promotional reward points to pay for travel instead of using hard earned cash. I had $450 worth of annual airline credits for American Airlines thanks to my American Express Hilton Aspire and my American Express Platinum credit cards. Something else you may not realize about these cards is that you can get them without paying the ~$500 fee if you’re active duty military.

So the flights cost me $150 and total rental car cost plus fuel was $236 per person.

Taking the Edge Off Rough Travel Times

Now I won’t lie and say that all of our flights were ideal. First of all, literally all of our flights were canceled at some point during the trip but we were able to salvage everything after hours of kicking and screaming to any airline related worker we could find. Even without the cancellations, we knew we’d have to sleep at the Los Angeles airport the first night.

So after eating at two Priority Pass restaurants for free thanks to one of my credit cards, we took off from Boston with some food for our Journey. I also got my first dinner at P.F. Changs in the LA airport for free thanks again to Priority Pass.

I honestly didn’t even mind that we had to sleep in the airport, especially after we found some cots that American Airlines offered and even this tower of pre-made sandwiches they were giving out to people who had to sleep in the airport.

I’m pretty sure we ended up with about 6 sandwiches and enough food to get us through a few nights when we landed.

Traveling with hiking bags and camp pillows make travel easy

Traveling with hiking bags and camp pillows make travel easy

Hotels $0

That’s not were the travel hacking ends in this story. Remember that hotel I mentioned living in? Well the hotel that was being paid for by my renter’s insurance because of a house fire. The insurance company kindly offered to pay for the hotels directly so I didn’t have to worry with it but I declined.

The reason I declined that offer was travel hacking. By getting a Hilton rewards credit card that automatically gave me diamond status and using some running promotions, I was able to at times get 40 points for every $1 I spent on the hotel. And for reference, the hotel ran in the ballpark of $8k per month. So I would cover the hotel, collect the points, and get reimbursed by the insurance company.

2.4 Million Hilton Points…

When it was all said and done, I had over 2,400,000 points. Yes…2.4 MILLION. So when we had winter on our heels and a truckload of points, you can see why we quickly dreamed up this Hawaiian adventure. We covered 10 nights in the hotel for 380k points and zero dollars cash. Five nights were in Kauai and five in Oahu.

We got a nice little cottage house in Kauai via my Hilton points

Food & Drinks - Six Days in Kauai: $35

First off I completely understand this sounds ridiculous and don’t blame you for being skeptical but let’s break it down.

As I mentioned, on the way to Hawaii, we stopped at three priority pass restaurants where we were given $172 worth of free food, free stuff from American Airlines lounge, and free sandwiches for the American Airlines passengers with overnight layover. As you can see below, we weren’t roughing it at all.

My first P.F. Chang experience made better by being free!

Once we were settled into our hotel, the free food continued. The Hilton we were staying at had one of the better breakfasts I’ve ever had at a hotel. It even had a large selection of made to order items and chef specials to include eggs benedict, mochi pancakes, and breakfast pizza.

Intermittent Fasting

We would eat so much at breakfast that we rarely even wanted lunch and we had a few dinners taken care of from food we brought along. That doesn’t mean we didn’t eat out at all.

Our first stop was to Tiki Tacos which was fantastic. Tacos are double or triple a normal taco, and we went with kalua pork ($7/taco), best fish taco ($8), polo Loco w/guac ($6). We split these and the purchase of some tequila, soda, and limes to make some margaritas so that came out to $21 a piece. Finally, we received two Mai Tais every day for free at the hotel.

The next couple dinners were from a rotisserie chicken, potato wedges, carrots and hummus that we bought at the grocery store for $8 a piece. In reality we were much more focused on just spending as much time and energy on hiking and viewing beautiful scenery in Kauai that going out and eating wasn’t a big concern.

We did however have one more star of the show before we headed over to Oahu and that was some famous Hawaiian shaved ice ($6). This stop was at JoJo’s in Hanalei Bay. What makes these different are having ice cream at the bottom and a cream syrup on top.

Hawaii Shaved Ice

Activities in Kauai: $237

It’s kind of funny but we spent way more money on excursions in Kauai than we did in Oahu even though Kauai is filled with so much free natural beauty and Oahu is seen as much more touristy.

That being said, I don’t regret these expenses one bit. Our first excursion was a $50 kayak tour down a beautiful river to an amazing waterfall. We got super lucky by having dry weather the week prior so a normally mud filled journey was nice and easy.


The next activity that we paid for was a steep price but one of the top things I would recommend to anyone visiting Kauai. We took a $187 helicopter around Kauai with some of the most amazing views I’ve ever seen in my life including this stunning view of the Na Pali coast.

Napali Coast

I won’t lie. This experience made me appreciate so much how well I’ve taken care of my finances. I keep my expenses so low that springing for something like a helicopter ride was a decision that I could make without even thinking about it. I swear there must have been 200 waterfalls and I ain’t exaggerating.

And I got a great paparazzi photo to go along with it ha

One day you live like your homeless, one day you jump on a helicop

One day you live like your homeless, one day you jump on a helicop

In reality there’s way too many amazing memories from Kauai that we snagged but I’ll put a gallery below for a few more we really liked

Food & Drinks - Six Days in Oahu: $66.54

Thanks to another hotel with free breakfast, we were able to keep things really cheap again. We knew between the hotel breakfast and leftovers from the Priority Pass restaurants that we’d need some way to not let food go to waste so we had food containers with us the whole time which was a huge help.

Four Seasons for Dinner - McDonald’s for Dessert

Several times we had breakfast bar food for lunch on the road. We did eat out a few times though including some ramen ($8.58), McDonald’s sundae ($1.98), another snow-cone trip ($3), and an incredibly affordable dining experience at the four seasons restaurant where we had food and a couple drinks right on the ocean ($21.95)

4 seasons restaurant

The star of the show though was at En Fuego which was a spot in a little strip mall where we split this massive combo that had a big chunk of ahi tuna, garlic chicken, rice, a salad, and some wantons ($7.50).


Then we rounded it out with a meet up with some friends at Encore saloon followed by Smith and Kings. I sadly didn’t get any pictures but Encore had great tacos and $3 pacificos. Smith and Kings had some really nice fancy cocktails. In total I spent $45 between those two.

Activities in Oahu: $0

That’s right. We didn’t do a single activity that we had to pay for. But you have to believe it wasn’t boring.

First, I have to give a huge shout out to Doug Nordman from Military-Guide who took me an Leslie out surfing two beautiful mornings at White Plains Beach.


Doug was so patient with us. Well, I should say me. Leslie was a natural and was riding waves from the start but I took a little more tutoring.

We also got to go out on a cool catamaran to snorkel with sea turtles. I have to give Leslie props again because she made some friends in Kauai who worked at the Oahu outfit and Instagram connections turned into free excursions.


Unfortunately we had a lot of plans altered due to rain. We didn’t get to hike at hardly any of the places we had hoped but Life-Pro-Tip, if it’s raining in Oahu, just head to the west side of the island and enjoy a nice day on the sand like at Electric Beach.

Just up the road from Electric Beach, we were directed to a cool site thanks to the nice lifeguards called the mermaid caves. It’s a little sketchy getting in and out of the caves. Imagine you’re walking along rock and decide to jump down a little hole in the ground with water…enter at your own risk for sure.


Was It All Sunshine and Rainbows…. Heck NO

We were a few hours from boarding our plane when we got a call that our flights were being cancelled and Alaskan couldn’t get us out for another two days. We were freaking out because we would lose two day of our Kauai portion which was our most anticipated.

That also meant two hotel nights and two rental car days. We start scrambling on Google Flights and miraculously found an American Airlines flight for only a few more dollars than what our original flight would have cost and Alaskan gave us a full refund. Things were good.

Wait…All of Our Flights End Up Cancelled?

Then there was the return flight from Hawaii. You guessed it. Flights got delayed so far that we wouldn’t make our connection in Los Angeles. This is vitally important because I had a plane to catch in Boston as soon as we got back.

I mean as soon as I got back. In fact we were landing at 5:30 P.M. and we were both due for a flight to Denver at 7:30 P.M. luckily from the same terminal. That’s a big problem already and now it just got worse.

Luckily we were both able to get redirected on different airlines yet again. This time for no additional cost because we booked through an agency for the return leg and they re-booked us tickets albeit on completely different routes.

So I flew from Oahu to Seattle, Seattle to Portland, Portland to Boston and landed just after 5:30 P.M. with my 7:30 P.M. flight looming. Now I couldn’t just go to my next flight. I needed my Colorado specific baggage because one does not go to Colorado in February without skiing.

Luckily, we had packed all of our Colorado gear over two weeks prior and dropped them off at a friends house. So when we landed, they swung by the passenger pickup line. We placed our Hawaii bags in the car and grabbed the Colorado bags like some type of hostage exchange and off we went.

Oh and I don’t even have time to explain the bit about me having no rental car or hotel reservations for Colorado due to a work travel system taboo. All I’ll say is people look at you funny when you’re calling help desks at 35k feet but thank goodness for Wi-Fi calling.

Who Cares About The Clouds

So what it wasn’t all perfect. We got an incredible vacation to Hawaii followed by a free one to Colorado thanks to it being a work trip. I was so proud at how we continued to adapt and never got angry at each other.

I know I’m blessed and maybe you feel more blessed or maybe you think you’re less blessed but if you’re reading this right now it means you have time to do so and access to internet so anytime something bad happens, just remember how much worse it could be.

Let’s Wrap This Thing Up

So just to help wrap up the spending totals

  • Transportation - $386

  • Hotel - $0

  • Food and Drinks - $101.54

  • Activities - $237

Total: $724.54


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