5 tips we used to save over $2600 on our trip to Hawai`i

budget, financial independence, frugal, how we win, travel

Much like our vacation to Iceland in the spring of 2017, our recent two week trip to Hawai`i was predicated on our desire to hike and experience the most exotic, beautiful, and lush destinations. As such, we didn’t travel hack it to an 85% savings rate like Asheville, Savannah, and St. Augustine, but we did save a good amount (like a couple thousand dollars) and wanted to share these actionable tips with you.

Our preference is to travel to our “bucket-list” destinations versus only traveling to locations based on the best deals/points to save money. It certainly didn’t hurt that we got to experience live flowing lava within about 20 feet of us that looked a little something like this:

Lava Flow 6 (2)

Dinner and a show, nice date night!

Before we delve in to how we saved money in Hawai`i, you might want to check out our previous travel hacking articles:

We’ll wait…

So, now that you are all caught up on our adventures, what did our Hawai​`​ian adventure entail? Flights from Florida to Kona, Kona to Honolulu, and Honolulu to Florida, 14 nights, two islands (Big Island and Oahu), and countless adventures. Our priorities are hiking and experiencing the beautiful landscapes this amazing world has to offer. While certain hikes in Hawai`i come with a parking / entrance fee, the vast majority are free and entail miles of beauty at no cost. Nature provides some of the best free entertainment (and exercise) out there!

If your ideal vacation involves parking yourself on a beach, Hawai`i certainly provides every opportunity for you to do that, and you can travel hack a beach destination itinerary relatively easy. Many other blogs will help you with that. We chose to explore and adventure as you’ll see in some of the pictures and descriptions below.

But first, here’s what we spent and what we saved.

Category Spent Saved Notes
Flights $33 $1,744 Unavoidable Fees, redeemed American Airlines miles to save on the 3 flights
Bag Fees $25 $50 AAdvantage comes with a free checked bag, we had to pay the baggage fee on the Interisland flight
Big Island Lodging $581 Averaged $83 per night (7 nights)
Oahu Lodging $289 $496 Averaged $96 per night (3 nights) for AirBNB’s. Savings came from Marriott Points (one night North Shore) and two nights of being housed by friends.
Rental Cars $520 $200 Booking through Autoslash saved $200 over booking directly.
Groceries $175 $140 We packed significant meals in our checked bag!
Dining $140
Gas $108
Misc. Fees $97
TOTAL $1,969 $2,630 Hey we saved 57%!



Sunrise hike into Pololū Valley


Patience and flexibility is key when booking American Airline award flights. We checked consistently for months, waiting for our exact criteria to be matched. We did this by defining our specific criteria, but being flexible with dates, and being ready to book as soon as the seats come available. Good things don’t last forever!

Where we weren’t flexible:

  1. We wanted to fly into one Island (either Oahu or the Big Island) and fly out of the other
  2. We wanted to have only one connection on the outgoing and return trip, and
  3. We wanted to pay with the most economical Economy MileSAAver points. Given the stresses of travel, limiting the number of connections was important as well as not having any wasted time flying back and forth between the islands. We also knew that we wanted somewhere around two weeks, which was the amount of time we felt would be worth it for the ~12 hours of travel each way, visiting two of the islands, and not leaving our offices in a bind.

Where we were flexible: 

  1. Primarily the dates as well as which island to visit first. So with the parameters set, we consistently checked for one-way flights to each island and waited for our exact criteria to be met. Finally, we were able to book our criteria: Tampa to Kona (through Dallas) and Honolulu to Tampa (through Dallas).

How we did it:

  1. We each used 45K American Airlines points to get to and from Hawaii. We also each used 7.5K American Airlines points to get from Kona to Honolulu. With under 52.5K American Airlines points each, the flights were paid for (except the minimal unavoidable fees).
  2. We both had signed up for the Citi Aadvantage credit card when offered at 60K bonus miles, fully paying for these flights with points to spare (total estimated savings of over $1,700).

Bag Fees Bonus:

American Airlines would have charged $50 round-trip for our one checked bag. Our previous Citi Aadvantage cards had both been cancelled, so no free bag perk there. This had me look at the Aadvantage Aviator Red card. For a $95 annual fee you get a free checked bag, priority boarding, and 60K sign-up miles (minimum spend of only one single purchase!)… therefore for a $45 fee on top of what I was going to be paying anyway for the checked bag, we might as well take advantage of obtaining another 60K American Airline points!  This is enough miles to get a round-trip flight to Europe or of course back to Hawaii with miles to spare! The $25 bag fee we did pay was related to the inter-island flight on Hawai`ian Airlines between Kona and Honolulu.

Note: Why did we need a checked bag? Usually we’re the type to maximize savings and not check bags at all by just being minimalist and going with carry-ons.  But you can’t bring hiking polls on a plane, so we check. Since we have to check, we cram as much as we can into the checked bag.


We stayed one night on a lava field… it wasn’t too cool. Hah! Get it?!


Big Island : We elected to stay with six different Airbnb properties for our seven nights on the island. That helped give us a variety of local experiences, meeting different hosts, and getting a feel for the variety of subcultures that permeate the island. As the Big Island is the largest of the Hawai`ian Islands (shocking, I know), we had our version of slow traveling the island, starting in Kona, heading North and eventually circumnavigating the island.  We strategically found Airbnb’s that helped (generally) keep each day’s driving to a couple hours or less from. The average price paid per night, including fees, was a very reasonable $83/night (definitely check the reviews!). We could have stayed on some of the big island resorts, but many have notoriously high fees (i.e. resort fees of $30/night and parking fees of $20/night). It made no sense for us to pay upwards of $50/night on fees AND burn through our points when we stayed in locations that were even better for our planned hikes and excursions.

Oahu : Oahu was a little bit more mixed, the island is much busier and more expensive for lodging. We also booked closer to our travel dates (and were traveling around spring break) which may have dwindled the available supply. Thankfully, we have two amazing friends who live on Hickam AFB and let us crash for two nights. We also took advantage of the Courtyard Marriott near North Shore for a night with available Marriott Points. While Waikiki has a majority of the resorts, similar to the Big Island, these often come with significant resort and parking fees (not as much of an issue if you don’t rent a car). Contrarily, the Courtyard Marriott near North Shore comes with no resort fees and a more reasonable $12.50/night parking fee ($10 when we visited). This property was charging over $300/night, so nice point redemption on that stay. The remaining three nights on Oahu were again spent in Airbnb’s close to our planned hikes at an average cost of $96/night.


Cue the Jurassic Park music… or the LOST ticking clock

Rental Cars:

Autoslash continues to be a fantastic website for finding and booking well priced auto rentals. We highly recommend you consider using them as a resource anytime you are looking for a car rental. They saved us well in the Southwest U.S., Asheville, and now Hawai`i with both bookings. We saved over $200 using Autoslash over booking directly through Hertz (which we had a fine experience and no issues with). Oahu does have a comprehensive bus system, but we opted for the car for convenience.


Eating out and enjoying local foods should be part of any trip you make. It’s a fantastic opportunity to sample new flavors, expand your pallet, and eat like a local, even if it’s just for a meal. With that said, Winning Williams likes to control our nutritional input, eating right and cost effectively. From a cost perspective, groceries in Hawaii are EXPENSIVE, especially compared to shopping at Aldi in Florida!

We try to control all variables that are in our power. Knowing how expensive groceries in Hawaii are, we started shopping in Florida, utilizing our checked bag to transport said food. We then supplemented with fresh goods upon arrival in Hawai`i (bread, tortillas, bananas, cheese, etc.) So what did we pack in our checked bag and could you do something similar to safe significant money while traveling: almonds, trail mix, beef jerky, peanut butter & jelly (supplemented with bread was a major lunch source), popcorn, tuna packets (major dinner source), instant potato packets (judge free zone right?), instant rice packets, and whatever else I’m forgetting at the moment!

There’s no question that we saved significantly by 1) grocery shopping and not dining out every meal and by 2) utilizing Aldi in Florida for non-perishables. We estimated $140 of savings from lower grocery costs alone.


On dining we spent a reasonable $140 over the two weeks which included delicious date night of Vietnamese food and ice cream, Malasadas (Portuguese donut), moco loco (rice topped with sausage, ham, and spam, fried egg, brown gravy), café’s, Hawaiian BBQ, to the basic we’re hungry and need cheap food now classics like Taco Bell and McDonald’s!


Many of the parks and hikes are free. A couple came with minimal ($5) or even as little as $1/per person fees. Completely inexpensive and worth it. The Volcano National Park was the most expensive with a 7-day park pass going for $25. It’s worth every penny to experience this national park!

If you would like more specific hiking/itinerary information, please feel free to reach out to us!


For reference, here’s a list of most of the hikes we did across both islands: Jagger Museum, Aiea Loop, Pali Puka, Diamond Head, Koko Head, Lanikai Pillbox, Makapuu Point, Ulakaa Trail, Keana Point, Laie Falls, Manoa Falls, Wiliwilinui Ridge, Pearl Harbor, Crater Rim Drive, Kalopa State Park, Kilauea Iki and Thurston Lava tube, Akaka Falls, Carl Smith Beach, Laupahoehow Point, Onomea Drive, Rainbow Falls, Peepee Falls, Lava Hike!, Lave Tree State Park, Mackenzie Recreation Area, Manua Kea, Pololu Valley, Wipio Valley, Honomalino Bay, Punaluu Black Sand Beach, Pu’ukohola Heiau Park.


We saw, we savored, and we saved! What are your next trip plans?


A BIG Thank You:

Part of our trip involved an amazing morning of surfing with the legendary Nords over at The Military Guide. He was very patient with us and we learned a lot! The surfing lesson was fun and exhilarating, but the conversation afterwards was equally rewarding. Being about to connect with and discuss our favorite topics with someone who has such a vast wealth of knowledge was great. We met Doug back in January at CampFI Southeast. We have made some great friends at events like these and what could have just been another day of hiking by ourselves turned into an amazing morning that was one of the highlights of our vacation. Actionable tip here is: be open to interacting with others. You might make new friends or connections that can have a positive lasting impact!


And the Videos:

Big Island:



2 thoughts on “5 tips we used to save over $2600 on our trip to Hawai`i

  1. So happy you guys had an amazing trip! Great write-up and fantastic savings. Now the only problem is that you’re likely addicted to Hawai’i (I am) and will need to go back. Maui and Kauai’i await. Next time stop over in Vancouver to adjust time zones and spread out the travel. You can stay with me anytime!


    1. We absolutely will take you up on that! We are actually thinking that our next big adventure may be a trip to the Pacific Northwest for the hiking and kayaking. 🙂 We will definitely keep you posted.


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