Awhile back I read a pretty savvy blog post about how to travel to Hawaii for free or nearly free.

I decided to give it a go myself, and what do you know… it worked!

Thanks to some travel hacking, we paid next to nothing for our flights and hotel, and even got an upgrade to a sweet suite.

Hawaii Spring Break

We spent 7 nights on Waikiki in Oahu this year, flying direct from San Jose to Honolulu.

It was the perfect time to visit. It was 82F and sunny every day (but 1) and 72F and comfortable every night. At home it was cold and rainy nearly every day.

We first spent 2 nights at the Sheraton Princess Kaiulani. I used to stay here often when I was shuttling between Seattle and Japan for work and I have to say the recent renovations make this feel like an entirely different hotel. It is really nice. And the view was great!

View from our balcony at Sheraton Princess Kaiulani

For the most part we spent the 2 days swimming in the pool with the kiddos, stepping across the street to the ABC to pick up poolside drinks, and then walking a block for sushi for dinner.

Then we spent 5 nights at the Royal Hawaiian which is at a whole ‘nother level. Winnie and I have stayed here in the past pre-kids and it still feels like a little oasis in the middle of chaotic Waikiki, with expansive gardens and grounds.

The view from our room was also nice, overlooking the pool (with waterslide) and beach.

Balcony view of pool and beach

A friend who lives on the big island stopped by for a few days and it was nice to catch up while the kids swam from 9 am to 7 pm every day. Jr loved the waterslide and the little one was happy to float about in the kiddy pool.

Winnie was able to slip away one night for some relaxation in the adult only infinity pool, which is shared with the next-door Sheraton.

We also spent a bit of time on the beach, and even got a little rainbow surprise after some light rain (which gave me a good excuse to pull out the laptop and submit our 2021 taxes.)

Rainy Sunny Day



How did we do on the travel hacking this time around? Not bad. Not bad at all.

We flew direct from San Jose to Honolulu on Alaska Airlines with a total cost for 4 people of $44.80, plus 80,000 Alaska miles. I grabbed these quick when I saw a flash sale back in February – cash price for the tickets was going to be an already great deal at ~$249 after taxes and fees, but that also meant low award redemptions of 10k miles each way. At these prices our redemption was worth ~$0.012/mile, about average for Alaska redemptions.

Most of these miles I have had hanging around for years after multiple credit card bonuses, but since I no longer have status on Alaska we were going to have to pay for checked bags. Checked bags are useful when traveling with 2 kids it turns out. That was an easy enough problem to solve – you get free checked bags with the Alaska Airlines credit card, which Winnie applied for… the Welcome bonus was a $100 credit (minus $75 annual fee) and 60,000 miles, which means we now have nearly enough miles to do this trip again next year.

Unfortunately our departure to Hawaii was delayed by a couple hours, but Alaska gave us vouchers for free food at the airport so coffee and fast food takeout were complimentary at least.

Since we were flying out of San Jose we needed a place to stay the night before departure and a place to park the car. Several hotels near the San Jose airport have great deals here… we paid $171.40 for a night at the Fairfield by Marriott which included up to 14 nights in their parking lot. By contrast a day of airport parking was going to be $24. For an airport hotel it was halfway decent.
(I originally booked this room at $178.xx, but checked the rate again just before the cancellation window ended and rebooked for $7 less.)

A drive from our place to San Jose does have some extra cost, especially with gas prices where they are… but we have an electric vehicle and get to charge for free, so just for fun I’m going to ignore this cost.

In Hawaii, I used 2 of the Marriott free night certificates we still had floating around for the Sheraton Princess Kaiulani. We had originally planned on using these for Christmas travel but plans changed (in part because expiration dates were extended through June 2022.) This saved us $400+, but we still had to pay resort fees of $33/day.

For the Royal Hawaiian we took advantage of the Stay 5 Pay 4 award redemption, paying 230,000 points for 5 nights (57,500/night.) I also used the 5 suite night awards that I got at the end of last year for reaching Platinum status… and they did upgrade us to the Historic Garden Suite. A quick look on the Marriott website had the cost of our room at ~$3,000/night so that worked out in our favor. (Had we not been upgraded, a standard room at the time of booking was $350 + taxes/fees/resort fee per night.)

At 800+ sq. ft. with 3 balconies and an incredible view it was a definite plus for our family holiday. Not bad for just the $42/night resort fee.

Historic Garden Suite

In both hotels I used my Platinum welcome amenity to get the breakfast benefit. This provided free continental breakfast for 2 for each day of our stay, or an $18 discount per person on any food we ordered. This made breakfast a $10 expense rather than a $30 expense.

The kids liked the waffles and pancakes and the view wasn’t too bad either.


There were some other expenses, of course. A taxi was ~$45 to/from the Honolulu airport. We had some nice meals both in and out of the hotels. The $50 in complimentary welcome drinks didn’t cover our entire beverage expense. But overall… it was a good redemption.


Flight to Hawaii for 4: $44.80
Airport hotel and parking, San Jose: $171.40
DinTaiFung dinner: $100
Breakfast at SJC: $0 (thanks to delayed flight vouchers)
Taxi to/from HNL: $90 (Uber surge pricing was $90 1-way)
Sushi: $200
Sheraton Princess Kaiulani: $149.15 (Food: $71.31)
Royal Hawaiian: $662.69 (Food: $414.94)
Other meals: $300 (?)
Final night teppanyak dinner with friends: $225

Total: ~$1,950
Total without travel hacking: ~$5,100 (not considering suite upgrade)

Other $ stuff

Because we had some costs at each of these hotels we earned some Marriott points. And because I paid those costs on a Marriott credit card, I got extra points. Let’s call it ~12,000 points, which would be worth ~$75 based on the redemption rates we got on this trip. It’s not a lot, but we will use those at some point.

I also used a Chase offer on this trip, which paid 15% back on Marriott transactions of $100+. Had I been smarter I would have utilized this fully, but I did get $22 back by paying for the Princess Kaiulani stay on this card.



Other Fun Stuff

Vacation wasn’t just swimming in the pool and eating sushi, it was also playing on the beach and eating teppanyaki.

* child models were compensated for their services

Playing in the sand

Burying your brother is fun

Eating sand is not


We went to Hawaii for spring break. Travel hacking saved us at least $3,000 and got us upgraded to a $3,000/night suite. Not bad.

I never regret visiting Hawaii and we are all looking forward to our next visit, just as soon as we build up enough miles :)


Be sure to check these out for planning your own Hawaiian getaway: