I’ve been on THREE trips to Hawaii in the last year with free flights AND free hotels ALL booked using points and miles.

That’s:

One trip to Maui staying at the super swanky Wailea Beach Resort and doing my favorites like sunrise at Haleakala, the Road to Hana, and soooo much beach time.

One trip to the Big Island staying at the Mauna Kea Beach Hotel to visit Hawaii Volcanoes National Park, tour a Kona coffee farm, and see the manta rays after dark.

And one trip to Maui staying at the Ritz Carlton Kapalua to explore the west side beaches, drive the Kahekili Highway, and do a day trip to Lanai.

WITH FLIGHTS FOR TWO PEOPLE.

Some people call it “travel hacking,” but basically…it’s using credit card points & mile systems to cover travel experiences, usually in a more luxurious way than you would normally if you were paying cash.

I’m certainly no expert in this industry, and I’m sure there are people who do this WAY better than me (and on a bigger scale), but I do travel to Hawaii a lot and I’ve saved a LOT of money using points and miles. So I’m going to tell you how I do it ; )

Using Credit Card Points to Travel to Hawaii

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First of all, a BIG Disclaimer: You should NEVER go into credit card debt to do this. And you should never use this to justify spending more money on things than you normally would because you’ll “get points.”

Also, let’s be clear. Stringing together free stays and amazing deals isn’t as simple as applying for one credit card and getting a free trip. It usually involves a little more strategy and synchronization (and sometimes just time to accrue points).

But here’s how to start:

Pick an Airline

I like Southwest (for reasons I have explained thoroughly here) and they’re the only airline I fly to Hawaii anymore.

They’ve also got BY FAR the easiest credit card point system to use.

I have this Southwest Premier Rapid Rewards Visa card through Chase. The current sign up offer is 50,000 points. Depending on where you live and fly from, that’s at least one completely FREE ticket to Hawaii and it could be two depending on the time of year (or more if you catch a crazy sale).

The card also gives you:

2 Early Bird Check-Ins per year (super nice when you’re going to Hawaii and the perfect seat is really important)

6000 anniversary points

3x points on Southwest purchases (more points for your next flight)

If you’re new to the “travel hacking” game, I think this is a REALLY good place to start. You’ll get some free flights right away and honestly, I feel like Southwest points rack up sooooo fast when you’re using the card for your everyday purchases.

Again, use >> this link << to get 50K bonus points when you sign up.

And read >> this post << for ALL the details on flying to Hawaii, why I like Southwest, and other airlines that may work better depending on where you’re flying from.

Pick a Hotel

Hotels and resorts are my FAVORITE thing to use credit card points on because there’s such a spectrum of what you could save. Flights cost what they cost, but using points on a luxury hotel could save you up to $1500 PER NIGHT.

My go to is Marriott. They have by far the most options available of any of the major hotel chains plus they’ve got a ton of luxury and boutique options (which are my favorite).

This Marriott Bonvoy Boundless card through Chase is probably my most used credit card.

As soon as you sign up for this card (and meet the minimum spend requirement) you get 3 FREE nights to use anywhere you want! The free nights attached to this card are good for hotels worth up to 50K points per night (plus you can add 15K points to each of those certificates) meaning you can book three nights at a hotel that’s valued at up to 65K points per night. There are quite a few hotels in Hawaii that will fall into that category (even more if you go during shoulder season – spring or fall).

Again, use >>this link<< to get 3 FREE nights when you sign up for this card.

But I have a “go big or go home” philosophy when it comes to travel, so I like to DOUBLE DIP on Marriott Bonvoy rewards with the Marriott Bonvoy Business Amex.

If you’re self-employed, a freelancer or contractor, a gig economy worker, if you own rental properties, etc…you qualify for a business card. (And you don’t need to be registered as an LLC or corporation. You can apply as a sole proprietorship with just your social security number.)

This card comes with three free 50K nights (the same as my Marriott Bonvoy Boundless through Chase) so right out of the gate, that’s SIX FREE NIGHTS.

Plus having both really gives you a jump on hitting an “elite status level” where you get perks like free breakfast, room upgrades, late check out, etc.

For more tips on booking Marriott properties in Hawaii with points (including how to maximize your free night certificates and which Marriotts I think are most “aspirational”), read >> this << post.

Two Free Nights at the Grand Wailea on Maui

Yes, yes, yes, I’m pretty loyal to Marriott. BUT here’s a “quick hit” that’s good to know about…

Maui’s flagship luxury resort, The Grand Wailea, is a Waldorf Astoria hotel which is owned by Hilton. If you scout around a bit, you can usually find it available for as low as 110K points per night. Right now, the sign up bonus on this Hilton Honors (Amex) is 155K.

And one of the Hilton loyalty program’s stand out features (to me) is that members can transfer points to one another without a limit (Marriott caps the number of points you can transfer to someone at 100K per year).

If your travel partner (husband, wife, daughter, friend, etc) also signs up for the card and gets the bonus, one of you can transfer your points to the other and you’ll have enough points total to book 2-3 nights!

That’s probably not going to be your whole trip, but you can either pay cash for the remaining nights (a major way to lessen the bill), or use your free nights at the end of your trip (maybe you’re staying in an affordable condo) as a big splurge.

Again, use >>this link<< to get your 155K point sign up bonus when you sign up for this card.