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  • Kaylee Maslowsky

Exploring Hawaii Part II – Keeping it Affordable

I’ve had the opportunity to travel to Hawaii four times and visit all four major islands. In total, I’ve spent approximately three months of my life in the aloha state.


“But Kaylee, Hawaii is so expensive!” says absolutely everyone.

Hawaii is one of the most beautiful places in the world. And you don't have to break the bank to travel there.

I’m here to share that it doesn’t have to be. My husband and I fell in love with the islands after spending 15 days in Oahu and Maui on our honeymoon. Truth be told, we spent WAY too much money on our first trip to Hawaii. At the time we didn’t know any better, and booked flights, accommodations and activities through a travel agent without doing any research. Big mistake. I don’t remember what that vacation cost us, but I guarantee that if we had booked everything ourselves using the strategies we know now, we could have spent triple the amount of time in Hawaii at the same price.


When planning any vacation, you need to be willing to do your research. If Hawaii is on your list (and it should be), follow my tips below on how to plan an inexpensive vacation to the Hawaiian islands.


Start saving those travel points.

I’ve bragged about the benefits of collecting loyalty points in a previous post and I’ll brag again. With the exception of our honeymoon, we have NEVER paid full price for flights to Hawaii. Back when you could actually use your air miles to fly, we’d make a conscious effort to collect miles and then use them all on a round-trip flight to Hawaii. Now that air miles are (for lack of a better word) useless, all you Canadians out there should be collecting West Jet loyalty points. Refer to my previous post on loyalty points for a quick refresher. West Jet flies direct from Vancouver to both Oahu and Maui. The flights aren’t actually that bad, and once you land in Hawaii you can easily hop around to other islands using Hawaiian Airlines. (Think $70 USD flights).


Rent a vehicle.

The best way to see Hawaii is to explore it on your own. While some of the islands are quite small, it’s not convenient or affordable to rely on public transportation or ride share options. And any type of group tour in Hawaii is going to be insanely expensive and usually rushed. Every island has such beautiful sights that you’re doing to want to explore at your own pace. Do yourself a favour and rent a car, allowing you the opportunity to forget about time and get lost in the beauty of the islands. We’ve used Discount Hawaii Rental Cars in the past and found that they have better rates than the larger car rental companies. Of course if you have points you can use toward car rentals, go that route first.


Now you might be tempted to opt for the mustang convertible, because let’s be honest, what’s better than cruising down the Hawaiian coastlines with the wind blowing in your hair, watching whales breach off in the distance. I’m telling you, DON’T DO IT. There are NO Hawaiian locals driving around in mustang convertibles. You are essentially telling the world that you are a tourist. While there’s virtually no crime present in Hawaii, vehicle break-ins at popular tourist spots are actually a thing. While you’re out hiking in a bamboo rain-forest, your mustang might be getting ransacked. You’re much better off getting a less expensive, smaller vehicle, which will help you get around in the more remote areas where the roads are extremely narrow. You and your wallet will thank me.

Enjoying a cup of java on our lanai in Kona, Hawaii.

Avoid the fancy resorts.

Sure. It would be lovely to stay at the Four Seasons Resort in the ritzy area of Wailea, Maui where serving staff literally walk into the pool, fully clothed, to offer you a juicy slice of pineapple. You’re in one of the most beautiful places in the world – is all that extra luxury really necessary? Instead of spending upwards of $600 USD a night to stay in a resort, I highly recommend you befriend Airbnb. Airbnb allows you to sort through accommodations based on your needs. The reviews are real and give you a great sense of what you can expect. I’m often more surprised when I stay at a hotel as opposed to an Airbnb. And the longer you stay, the less you pay. Many property managers will offer a discounted rate the more time you plan on spending at your accommodation. I've been fortunate enough to stay in beautiful condos with laundry, full kitchens, and unbeatable ocean views for around $200 USD a night (taxes and cleaning fees included).


You will also save a ton of cash by not having to eat out every meal, or pay those exorbitant resort fees at the end of your stay.


Stock up at Costco.

All four major islands (even sleepy Kauai) are equipped with a Costco. This is ALWAYS our first stop after picking up our rental vehicle. This is the only place you should be purchasing your booze and food from. Once you get into the touristy areas, grocery stores are ridiculously expensive. Stock up in advance, and save yourself a ton of cash.

Nothing better than happy hour drinks oceanside in Maui.

Can you say happy hour?

Ah happy hour. My favourite time of the day. Happy hours are huge in Hawaii and you’d be silly not to take advantage of the deals offered. Between 3:00 p.m. and 5:00 p.m. daily, we’d find ourselves on a patio for happy hour priced drinks and appetizers. Eating out in Hawaii can be extremely expensive, so happy hour prices are a great way to experience new restaurants and different types of food without breaking the bank. Of course you will want to go out for a few breakfasts and dinners during your stay, but you certainly don’t need to everyday. That’s why you stocked up at Costco. ;-)


Sign up for timeshare presentations.

Yes, you read that right. While I am in no way recommending you actually purchase a timeshare (not a cost savings at all in my opinion), you should be taking advantage of the perks being offered for attending a timeshare presentation. This is your opportunity to take in a traditional luau, golf a world-class course, or spend an evening at a beautiful restaurant. All that’s required? Having a free breakfast and touring around a beautiful resort for 90 minutes. Don’t let the presentation cut into your precious vacation time and plan to attend on a rain day. You only have to be present for 90 minutes in order to get your free perk. So as long as you don’t actually get conned into buying a timeshare (these sales people are gooood), this is an amazing opportunity to experience a beautiful resort (surely an upgrade from your Airbnb) and get an amazing perk in return.

A complimentary round of golf? Yes please!

Hawaii doesn’t need to be an expensive vacation. These strategies will significantly cut down your costs while still allowing you to have a kick-ass vacation.


Do you have other questions about how to make your vacation to the Hawaiian islands affordable? Subscribe to my blog and ask away!

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