How My Family Travelled to Hawaii for Cheap


A couple years ago, my family visited Maui and Oahu, and ever since then, we’ve been longing to return to Hawaii. This March Break, we finally made it happen and visited the Big Island (Hawai’i) and Kauai.

Travelling to Hawaii can be pricey, but there are multiple strategies that can be employed to soften the blow on your wallet.

On our most recent trip, we ended up spending under $3,000 (CAD) on flights and accommodation for 11 nights in tropical paradise with a family of five. Read on to learn how we did it.

Our Hawaiian Itinerary

Initially, we had planned to only visit Big Island (Hawai’i), but in the end, we decided to add a few more nights and visit Kauai, the last remaining island on our Hawaiian bucket list.

Maha’ulepu Heritage Trail, Kauai

We flew from Toronto to Vancouver to Kona with WestJet, and then stayed on the Big Island for seven nights. During this time, we moved around the island and stayed in three different areas: Kona, Waikoloa, and Volcano.

After these seven days, we flew from Kona to Lihue, Kauai on Hawaiian Airlines, where we stayed for four nights.

Kauai is a small island, and you could definitely stay in one hotel for the whole duration of your trip, but we ended up splitting our time between Princeville and Koloa.

Coming home, we flew United Airlines from Lihue to Toronto via Denver.

Amys Hawaii Trip

Saving on Our Flights

Generally speaking, you can expect to pay $700–1,000 (CAD) for a single round-trip flight to Hawaii, and you can expect to pay even more if travelling during peak periods like March Break.

For our family of five, we knew we could be looking at around $5,000 (CAD) just for the flights alone. Instead, we spent just under $800 (CAD).

Flight from Toronto to Kona, Big Island

We flew to Big Island using our WestJet dollars and the annual companion vouchers that came with my and my husband’s WestJet RBC® World Elite Mastercards.

Our redemption for five passengers looked like this:

  • Two companion vouchers
  • 439 WestJet dollars × three passengers
  • $665 (CAD) in taxes and fees for five passengers

Normally, there is a $399 base fare for the second passenger when using the companion voucher for Hawaii. However, WestJet sometimes runs a promotion offering a special $0 base fare companion voucher.

My husband and I both signed up for the card during one of these promotions in 2021, which is part of why this redemption came to the price as low as it did.

Flight from Lihue, Kauai to Toronto

Our original return flights were booked from Kona to Toronto on United Airlines with a layover in Denver for $1,560 (USD) for our family of five. Rather than use cash, we were able to use my United TravelBank credits.

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A great thing about many of the American airlines is that they no longer charge change fees. This meant that when we decided to return from Kauai instead of Big Island, we only had to pay the difference in fare for the new routing, which came to $21 (USD) per passenger for a total of $105 (USD) for all five of us.

Inter-island flight between Big Island and Kauai

To get from Big Island to Kauai, we flew a one-hour flight with Hawaiian Airlines for $85 (USD) per passenger, for a total of $423 (USD). I booked this flight through Capital One’s travel portal so that I could redeem the $300 (USD) annual travel credit that comes with my Capital One Venture X, thereby reducing my out-of-pocket cost to $123 (USD).

This meant that in total we spent only $976 (CAD) on all our flights!

These are just some of the examples of the many ways you can save on flights. Another common way to save on flights is through points redemptions.

As an example, a one-way flight between Canada and Hawaii can be booked for 22,500 Avion points or 12,500–17,500 Aeroplan points from Western Canada, and 27,500 Avion points or 17,500–25,000 Aeroplan points from Eastern Canada.

Accommodation on the Big Island

Aside from getting to and from Hawaii, accommodation can quickly become quite expensive. Luckily, we were able to significantly offset our costs using our Miles & Points strategy.

Staying in Kona with Marriott Bonvoy’s Annual Free Night Awards

The first and last nights of our stay on Big Island were spent at the Courtyard King Kamehameha’s Kona Beach Hotel.

Its proximity to the airport makes it a convenient hotel for late-night arrivals and early morning departures, which was exactly the situation we found ourselves in. Our WestJet flight arrived at 10pm the first night, and our flight departing for Kauai departed at 9:57am.

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Courtyard King Kamehameha’s Kona Beach Hotel – Beach

My husband and I both redeemed our annual Free Night Award worth 35,000 points from our Marriott Bonvoy American Express Cards for these two nights. At the time, the nightly cash rate was $370 (USD), but with the Bonvoy Free Night Award redemptions, we only had to pay $25.96 (USD) per night in taxes and fees.

Unfortunately, current redemption rates for this hotel have increased to around 59,000 Marriott Bonvoy points per night, so you’d need to use a Free Night Award worth 50,000 points with a top-up to enjoy a redemption similar to ours.

To earn Free Night Awards worth 50,000 points apiece, consider signing up for the Marriott Bonvoy Business Card from American Express US, which currently comes with a welcome bonus of five Free Night Awards worth 50,000 points each.

Staying in Waikoloa on an Encore Package with Marriott Grand Vacations

For the next four nights on Big Island, we stayed at Marriott’s Waikoloa Ocean Club, a Marriott Vacation Club property, on a timeshare package. If you’re not familiar with these, check out my previous post on how to leverage them for your vacations.

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Marriott’s Waikoloa Ocean Club – Exterior

The last time we were in Hawaii, we stayed on two such packages, one at the Marriott Maui Ocean Club and the other at Grand Islander by Hilton Grand Vacations.

Often, if you decline to buy a timeshare package during a preview presentation, the sales representative will offer you a repeat or Encore Package, which is kind of like a second chance to experience their vacation clubs for the still undecided.

After our stay at the Marriott Maui Ocean Club, we were offered an Encore Package for $1,295 (USD) for four nights in Hawaii. Our initial preview package was only $1,098 (USD) for five nights, after paying an upgrade fee of $299 (USD) for a one-bedroom suite to accommodate our family of five.

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If you’re wondering why we bought the Encore Package rather than just a new preview package, this was for a couple of reasons.

First, we knew we wanted to return to Hawaii, and we knew that preview packages to Hawaii are not always available.

Second, a night at any of the Marriott Vacation Clubs in Hawaii typically costs $600–1,000 (USD) per night, so we knew we were still getting a great bargain with the Encore Package. Marriott’s Waikoloa Ocean Club, where we stayed on this trip, currently costs between $800–1,000 (USD) per night.

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As a final note on our stay at the Marriott’s Waikoloa Ocean Club, we really appreciated that all base rooms are one bedroom suites rather than studios, so there was no need to pay additional fees for a suite upgrade to fit our family of five.

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Marriott Waikoloa Ocean Club – One-bedroom suite

Staying in Volcano on Scene+ points

We spent one night in Volcano to visit Hawaiʻi Volcanoes National Park.

The closest chain hotel to the national park is the Grand Naniloa Hotel Hilo, a DoubleTree by Hilton, which is a 40-minute drive away. If you book far enough in advance, this hotel is quite cheap at under $200 (USD) a night.

As our time in this area was limited, for convenience we opted to rent an Airbnb that was in the heart of Volcano. The spacious and modern two-bedroom bungalow was $391.56 (CAD) for the night.

To help cover the cost of this night, I used my Scotiabank Gold American Express® Card to pay for the stay, and then subsequently offset the cost using my Scene+ points.

I also made the booking through British Airways Executive Club’s Airbnb portal to maximize the points I could earn from the rental. By doing this, I earned 2 Avios per US dollar spent.

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In total, we spent just over $1,800 (CAD) for a week’s worth of accommodation on the Big Island.

Accommodation on Kauai

In Kauai, we stayed one night at another timeshare property, The Westin Princeville Ocean Resort Villas, followed by three nights at the Grand Hyatt Kauai.

Staying in Princeville on Marriott Vacation Club Points

No, we didn’t end up buying into the Marriott Vacation Club to gain access to the Westin – my parents did, many years ago when owning a timeshare was a popular trend.

My parents then generously let me redeem some of their points for our night at the Westin Princeville Ocean Resort Villas.

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The Westin Princeville Ocean Resort Villas – Exterior
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The Westin Princeville Ocean Resort Villas – One bedroom suite

If you don’t know anyone who owns a Marriott Vacation Club, not to worry. There are websites like Redweek.com that facilitate the rental of timeshares, allowing you to access substantial savings.

For example, on the Redweek website, you can rent a one-bedroom villa for only $214 (USD) per night versus the $1,067 (CAD) it’s listed for on Marriott’s official website.

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Staying in Koloa on Hyatt points

For our last three nights in Kauai, we stayed at the Grand Hyatt Kauai, often touted as the best property on the island.

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Grand Hyatt Kauai – Exterior

I redeemed 35,000 World of Hyatt points per night, for a total of 105,000 points for our stay. The cash rate was listed at over $1,000 (CAD) per night, so I was getting a value of 2.8 cents per point, which is a good value and saved us a lot of money.

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One thing I love about the World of Hyatt program is that you don’t pay any fees or taxes on award stays.

My World of Hyatt points were earned through my Chase Sapphire Preferred and Chase World of Hyatt credit cards, but if you don’t have a means to obtain these US credit cards yet, you can see if it would make sense to buy points to cover your stay.

Buying Hyatt points to redeem for a stay, especially during a promotion, can sometimes actually end up costing you less than paying cash, so it’s always worth looking into this option when planning your trip.

By using Hyatt points and gifted timeshare points, in total, we spent $0 for our accommodation on Kauai.

What Did We Spend Our Money On?

Saving money on our flights and accommodations freed up our funds for indulging in other fun things, namely food & experiences! 

Of course some of the best experiences – such as like hiking the crater of a volcano on the Kilauea Iki Trail – are free, but it always helps to have more disposable income to spend on the ones that aren’t.

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Here are some pretty awesome experiences and activities we did as a family on the Big Island and Kauai:

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Helicopter tour with Island Helicopters Kauai
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Bird’s eye view of Nāpali Coast

Conclusion

The biggest costs on any vacation are usually airfare and accommodation, and accommodation costs are particularly high in Hawaii, so finding ways to save is key.

Credit card benefits and points, as well as timeshare vacation packages and rentals, are just a couple of ways to help keep your costs down.

By saving money on some things, you can then have more at your disposal to cover other expenses or perhaps even your next trip.

I hope you found this article helpful, and if you have any more creative ways to save on vacations or any go-to tips, I’d love to read them in the comments below.





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