Travel Hacking: How I Get Free Flights & Hotels in Hawaii

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


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. 


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

This post may contain some affiliate links, which means I’ll make a little money on anything you choose to purchase. But of course, I only recommend my absolute favorites to you. Thank you for supporting the brands that make HulaLand possible.

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.

Here’s one more really important thing you need to know before your Hawaii trip…

Reservations You Need to Make BEFORE Your Hawaii Trip

You’ve got your airfare, hotel, rental car and your big activities booked, so you should be good to go, right? Wrong!

Travel is BOOMING in Hawaii so a lot of state and national parks used the closure and reopening to institute reservation systems at some of the island’s most popular spots to make things a little more sustainable.

That means that there are now over half a dozen sites (beaches, trailheads, etc.) that require advance reservations. And some sell out well before you arrive on the island so you really need to have some sort of a plan.

I recently saw somebody in a Hawaii travel group post in a panic that they didn’t know they had to make reservations for things in advance…they thought they could just show up and “go with the flow.” I was tempted to say, well, “as long as the flow doesn’t take you somewhere that requires reservations, you can!” ; )

But I don’t want YOU to be that person, so I’ve pulled together a list of all the places you need to reserve entry in advance (plus all the details on booking windows, price, links, etc.) and a handful of popular tourist hotspots that book out really far in advance too.

Haleakala National Park (Maui)

To visit Haleakala National Park for sunrise at the summit, you must make reservations in advance here.

Reservations are required to enter the park gates between 3AM and 7AM (sunrise hours).

Online reservations are $1 per reservation/vehicle PLUS you’ll pay the park entrance fee of $30/vehicle when you arrive (National Park annual passes are also accepted at the gate).

The reservation booking window opens 60 days in advance at 7AM HST. There are also a limited number of tickets released two days before.

You can make one reservation every three days with the same account. So if you want to make reservations for back to back days (in case of weather/conditions), you’ll need to do so with separate accounts (email addresses).

If you can’t get reservations for sunrise, you can enter the park anytime after 7AM without reservations. The summit is spectacular during the day and you don’t need reservations for sunset.

I strongly recommend creating an account before and making sure you’re logged in at 7AM HST because it’s not uncommon for reservations to sell out quickly.

Waianapanapa State Park (Maui)

To visit Maui’s famous black sand beach at Waianapanapa State Park on the Road to Hana, you must make reservations in advance here.

Reservations are required to visit the beach and are distributed in windows from 7AM-10AM, 10AM-12:30PM, 12:30PM-3PM, and 3PM-6PM. And they are pretty strict about exiting by the end of your window time (you can arrive anytime within your window).

It’s $5/person to enter plus $10/vehicle to park and those fees are paid when you book your time slot.

Reservations open up 30 days in advance.

Iao Valley State Park (Maui)

To visit the lush, green mountains and hike at Iao Valley State Park, you must make reservations in advance here.

Reservations are offered for 90 minute time slots beginning at 7AM and ending at 6PM. They ask that you arrive within the first 30 minutes of your time slot.

Entry is $5/person plus $10/vehicle to park.

Reservations open up 30 days in advance.

Diamond Head (Oahu)

To hike to the top of Waikiki’s famous Diamond Head, you must make reservations in advance here.

Reservations are offered in two hour increments beginning at 6AM (6AM-8AM, 8AM-10AM, etc.) and ending at 6PM. If you’re parking onsite, they ask that you arrive within the first 30 minutes of your reservation window.

Entry is $5/person plus $10/vehicle to park.

Reservations open up 30 days in advance.

Tip: I recommend booking one of the first two time slots because there isn’t much shade on this hike and it gets pretty hot.

Hanauma Bay (Oahu)

To snorkel at Oahu’s pristine Hanauma Bay, you must make reservations in advance here.

Entry times are staggered in 10 minute increments from 7AM to 1:20PM with roughly 1000 slots being assigned in advance every day.

Reservations can be made two days in advance and they open at 7AM HST. They’re usually gone in minutes (if not seconds).

If you’re unable to get an advanced reservation, you can try for a day of, walk in ticket. They open at 6:45AM and they only have a limited number available. Everyone in your group needs to be present when you purchase your tickets in person.

There are no reservations for parking and it’s first come, first serve. $3/vehicle.

It’s $25/person to snorkel at Hanauma Bay (12 and under, active military, and locals with HI ID are free).

The Hanauma Bay Nature Preserve is open Wednesday through Sunday (CLOSED MONDAY AND TUESDAY) from 6:45AM-4PM. Last entry is at 1:30PM, the beach is cleared at 3:15PM and you have to leave the facility by 4PM.

Jellyfish patterns can also affect whether or not the bay is open so double check the day before/day of.

USS Arizona at Pearl Harbor (Oahu)

If you want to take the boat tour at Pearl Harbor out to the USS Arizona, it’s recommended to make advance reservations here.

Online reservations are guaranteed a specific boarding time to go out to the USS Arizona. If you’re unable to get an advance reservation, you can wait standby when you arrive. The line could be short (15 minutes or so) or long (hours) and it just depends on the day (if they’re having problems with the loading dock sometimes they don’t take many from the standby line) and the time of day.

Reservations are supposed to open up 60 days in advance, but keep an eye on your exact dates, because lately they’ve actually been opening up about 57ish days in advance???

They also release a small batch of tickets the day before.

The boat ride out to the USS Arizona is free, but it’s $1 to make the reservations online.

They recently started charging $7/vehicle for parking at Pearl Harbor.

Haena State Park / Kalalau Trail (Kauai)

If you want to hike Kauai’s famous Kalalau Trail, you must make advance reservations here.
You’ve got three options here:

1) Parking & Entry: This is the most flexible option and also the most limited. THESE RESERVATIONS SELL OUT IN LESS THAN A MINUTE. There are three time slots available: 6:30AM-12:30PM, 12:30PM-5:30PM and 4:30PM to sunset. You can purchase multiple time slots if you want to stay longer. It’s $10/timeslot (parking) plus $5/person and you have to reserve every person when you initially book. Everybody has to arrive in the same car and your ID needs to match the reservation.

2) Shuttle & Entry: If you can’t get parking at the trailhead, there’s also a shuttle option. Shuttle reservations are $35/person (16+), $25/person (ages 4-15), 3 and under can ride free. The shuttle runs every 20 minutes 6:20AM to 6:40PM.

3) Entry Only: If you’re a Hawaiian resident (with HI ID) or someone WITH a Hawaiian resident, you can purchase entry only for $5/person with no advance reservations. Also, if you’re walking or biking to the trailhead you can do this option. But there is NOWHERE to park in the area to walk in. So this really only works for those with bikes or who are staying close enough to walk. They will tow your car if you park outside the designated areas.

The reservation window opens 30 days in advance at 12AM HST. The parking & entry option usually sells out in a minute, but the shuttle availability will last longer.

There are a TON of FAQs here including the possibility of snagging a canceled reservation.

Other Things to Book in Advance

Hawaii is a busy place these days! Besides the state and national parks above, here’s a handful of miscellaneous things you should make reservations for in advance (if they’re on your radar):

Mama’s Fish House (Maui): The iconic spot is the most popular restaurant in Hawaii and dinner reservations usually start filling up about 6 months in advance (they open up bookings 18 months in advance). Make reservations through their website and if the dates you want are already booked, you can join a waitlist. Most people have pretty good success getting in on the waitlist (even if it’s for lunch).

Old Lahaina Luau (Maui): Honestly, any luau you’re planning to attend you should book early, but most people are usually shocked how far out the Old Lahaina Luau books out. Book it as soon as you know your dates (I think they open at the six month window). They also have a waitlist.

Kualoa Ranch UTV Tour (Oahu): Everybody loves Jurassic Park so getting to ride UTVs where they filmed the movies is very popular. The ranch offers a lot of different tours but the UTV tours usually book out a couple of months in advance.

Spa Reservations: If you’re staying at a resort with a spa (or planning on visiting one), don’t wait until you arrive to make your reservations. I’d make them at least a month in advance.

Tee Times: Same for golf, reserve your tee times well in advance.

Dining Reservations: Any “fancy” or resort restaurant is likely to be booked up these days so if you like having a nice dinner every night, make your plans in advance.