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If there’s one question I get asked all. the. time. (especially by people who know me in real life) it’s how I’m able to afford to travel as much as I do and stay in really nice places. Especially in Hawaii.

Well, this being my job, I spend a fair amount of time tracking price patterns and researching deals, but honestly…a LOT of my travel is covered by using points and miles through credit cards and loyalty programs.

Some people call it “travel hacking” (I think it’s just managing your resources smartly ; ) Basically, it’s using credit card point & 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. And I’m going to tell you how I do it ; )

The Short List

If you just want the cliff notes, here’s my list of credit cards and loyalty programs that I use frequently:

Southwest Premier Rapid Rewards Visa (Chase)

Marriott Bonvoy Boundless (Chase)

Chase Sapphire Reserve

But keep reading for ALL THE DETAILS about how I make these cards work for me and all of my trips to Hawaii.

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).

And 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.”

How I Get Free Flights & Hotels in Hawaii

Here’s how this post is going to break down. I’m going to give you info on:

My favorite airline & how I get free flights to Hawaii through them
My favorite hotel brand & how I get free rooms in Hawaii through them
A bigger strategy that involves using multiple credit cards/loyalty programs, but which yields much bigger perks
Other credit cards/loyalty programs that may work better for you depending on where you live/travel from

And while I’m laying all of this out there in terms of traveling to Hawaii, it works for anywhere you’d travel.

Promise me this: Read this WHOLE post before you start clicking around and signing up for things. It’s a layered approach and depending on where you are in your “travel hacking journey” and where you are in the country (physically where you live), one of these things may work better for you than others.

Okay? Ready to go? Let’s dive in!

Airline (Southwest)

I think it makes sense to pick one airline to focus on. This could vary depending on your home airport and which airlines operate out of there.

For me personally, I fly out of Tulsa, OK so options are LIMITED and I’m guaranteed to have to make a connection somewhere else.

I think Southwest is the most straightforward airline to book using points. And in the last 5-6 years, it’s become the ONLY airline I fly domestically. The point values for flights directly correspond to the cash price. And they don’t throttle the availability of point redemptions. If there’s a seat available on that plane, they’ll let you book it for cash or for points.

A lot of bigger airlines only reserve so much capacity on each flight for point redemptions so if you don’t book immediately when the booking window opens, you can’t use your points even if you have them to burn.

Anyways, so I think you get a lot of bang for your buck using Southwest miles to fly to Hawaii. Plus you get free bags ; ) And their cancellation and modification policies are super reasonable.

Here’s what Southwest flights to Hawaii look like.

You can fly direct to Hawaii on Southwest from:

Las Vegas (LAS) to Maui (OGG), Oahu (HNL), Kauai (LIH), Big Island (KOA)

Oakland (OAK) to Maui (OGG), Oahu (HNL), Kauai (LIH), Big Island (KOA)

Phoenix (PHX) to Maui (OGG) and Oahu (HNL)

Sacramento (SMF) to Oahu (HNL)

San Jose (SJC) to Oahu (HNL)

Los Angeles (LAX) to Oahu (HNL)

Long Beach (LGB) to Oahu (HNL)

San Diego (SAN) to Oahu (HNL)

If you live in one of those cities, you are GOLDEN. You’ll be able to find flights fairly cheap (and low miles) and it’s an easy 4-6 hour flight.

If you do not live in one of those cities (hi, it’s me), you’ll need to do a little research into which (if any) you can fly directly from your city to.

For example, flying from Tulsa, OK, I can get direct flights on Southwest daily to Las Vegas and Phoenix, making those options for me to get to Hawaii (Southwest won’t sell you a through ticket with more than one connection).

Now, the flight times have to line up so you’ll be able to do it all in one day, but I can usually make something work even if it’s just on certain days of the week.

Maybe you noticed that from Las Vegas you can fly to all four of the main Hawaiian Islands, and that’s not by accident.

First of all, Las Vegas is a wildly popular destination with Hawaiians so there’s always demand for those flights.

Second, most mid-sized cities in the US have direct flights to Las Vegas making it the perfect “hub” for Southwest to use for people who don’t live in one of the cities with a direct flight and need to make a connection.

Live in Minneapolis, Dallas, Denver, Memphis, Albuquerque, Charlotte, Chicago, Columbus, Pittsburgh, etc? You can probably get a direct flight to Vegas which opens up Hawaii to you.

So flying to Hawaii from Las Vegas, Oakland, Phoenix, Sacramento, San Jose, Los Angeles, Long Beach, or San Diego will generally be fewer points (and a cheaper cash price) than if you have to make a connection, but you’ve got options. And that’s not even taking into account a sale.

Okay, so how to “hack” that?

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.

Hotel (Marriott)

If we’re talking major hotel chains/loyalty programs, you’ve really got three options: Marriott, Hyatt, and Hilton. Each of those “chains” has dozens of sub brands, but those are the three big buckets we’re dealing with.

All of them have pros and cons, but it’s undeniable how big Marriott’s global footprint is. No matter where you go in the world, there are almost exponentially more Marriott options than Hyatt and Hilton.

And that holds true in Hawaii.

So if you’re picking ONE hotel program to “work.” I can’t really recommend anything other than Marriott. And as you’ll see, hotel perks and rewards rack up a lot faster when you keep loyalty to the brand.

Okay, so I know you’re familiar with “Marriott,” but you may not realize exactly how far the Marriott brand reaches these days.

Besides the traditional Marriott marquis hotels, Marriott’s brands in Hawaii also include Sheraton, Westin, Ritz Carlton, Courtyard, Residence Inn, Marriott Vacation Club, and the Luxury Collection & Autograph Collection (collections of boutique hotels like the Royal Hawaiian, Moana Surfrider, Mauna Kea Beach Hotel, and the Laylow – these are some of my favorites ; )

So there are a LOT of great hotel choices in Hawaii under the Marriott umbrella – whether you’re looking for a once in a lifetime destination resort, a boutique hotel with fun vibes, or a good bang for your buck hotel.

I have stayed at some truly world class resorts in Hawaii for FREE using Marriott points including:

Ritz Carlton Kapalua

Mauna Kea Beach Hotel

Wailea Beach Resort

St Regis Kauai (now the 1 Hotel Hanalei Bay)

And some of these places had cash prices over $1500/NIGHT!!

I could NOT do this without my Marriott Bonvoy Boundless card through Chase.

Now I’ll level with you…you are not going to sign up for this card and book a week long trip at the Ritz Carlton on Maui next week. That’s a longer game ; ) But it’s totally possible if you work the program.

Here’s what you will get as soon as you sign up for this card (and meet the minimum spend requirement): 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.

In Hawaii (depending on dates), that could work at hotels like:

Oahu: The Laylow, Royal Hawaiian, Moana Surfrider, Courtyard Waikiki Beach, Sheraton Princess Kaiulani, Waikiki Beach Marriott, Renaissance Honolulu Hotel, AC Hotel Honolulu, Residence Inn Kapolei, and Courtyard North Shore.

Maui: Sheraton Maui Resort, Westin Maui Resort, AC Hotel Wailea, Courtyard Kahului

Kauai: Sheraton Kauai Coconut Beach Resort, Sheraton Kauai Resort

Big Island: Courtyard King Kamehameha’s Kona Beach Hotel, Waikoloa Beach Marriott

Besides the initial free nights, here’s why I love my Marriott Bonvoy Boundless card:

It comes with 6x points per $1 spent at Marriott hotels. Added to the points you get through the Marriott Bonvoy loyalty program, and you’ll get 17x points per $1 that you spend at Marriott hotels. That’s hotels anywhere. Need to stay at a Courtyard Marriott overnight on a road trip back home to see the family? Pay for it with your Bonvoy card and those points start to rack up REALLY fast. This is a GREAT card if you travel in general just here and there.

15 Elite Night Credits each year. Marriott’s status tiers are determined by how many nights you stay per year, but there are ways to boost your “night count” without actually sleeping in a Marriott bed. Basically Silver status is 10 nights, Gold is 25 nights, Platinum is 50 nights, Titanium is 75 nights, and Ambassador is 100 nights per year. Elite Night Credits are not free nights, but they’re credits toward your annual night count which determines which kind of perks you get when you DO stay at Marriott hotels. Higher status levels like Platinum, Titanium, and Ambassador may have access to perks like suite upgrades, free breakfast, and lounge access. So with this card, you get automatic Silver status and a jumpstart to a higher level of status without having to spend all of those nights in a hotel.

Plus every year on the anniversary of the date you opened your card, you get a free 35K/night free night certificate.

But I’ve saved my favorite thing about using Bonvoy points to book Marriott hotels for LAST:

When you book four nights using points, you get a FIFTH NIGHT FREE. So after I use my free night certificates (that have max point values like 50K or 35K per night), I only use my Marriott points for “big” stays where I have enough points to book four nights and get the fifth free. It’s by far the best way to max out the value on your points.

Side note: You cannot combine free night certificates with points to take advantage of the fifth night free promo.

Last year, I cashed in 325K points to stay for 5 nights at the Mauna Kea Beach Hotel on the Big Island. And I’m getting ready to stay at the Ritz Carlton Kapalua for 5 nights for 330K points.

And obviously, if you’re not staying at premium luxury properties, you can get stays for a LOT less. Or stay a lot longer ; )

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

I mentioned a list of hotels above that are good places to get the best “bang for your buck” on points and use free night certificates above, but if you’re like me, and you have a “bucket list” of great hotels, here’s also a list of the top aspirational Marriott properties in Hawaii (places that are worth hoarding your points for a big splurge):

Wailea Beach Resort (Maui)

Ritz Carlton Kapalua (Maui)

Koloa Landing Resort (Kauai)

Mauna Kea Beach Hotel (Big Island)

Royal Hawaiian (Oahu)

Moana Surfrider (Oahu)

The Big Guns: Chase Sapphire

Okay, we’ve talked about the two specific brand programs and cards that I use, but if you’re serious about travel hacking, you can’t ignore the Chase Sapphire.

This is the granddaddy of all cards if you’re in the travel game. It’s actually two cards:

Chase Sapphire Preferred

Chase Sapphire Reserve

Let’s call them jr. and sr. ; )

Both of these cards operate with Chase Ultimate Reward points which are widely considered to be the most valuable and most versatile points in the travel industry. And it’s mostly because they’re part of a larger travel network.

Chase Ultimate Rewards has partnered with major travel brands like Southwest, Marriott, Hyatt, British Airways, etc. so you can transfer your points to those networks and book directly but they also have their own travel portal where you can book your travel and receive more value for your points.

Both of these cards have access to this network, but the Sapphire Reserve card comes with significantly more travel perks (and a significantly higher annual fee).

Basically, if you’re a semi-frequent traveler, you MUST have one of these cards.

BESIDES the amazing flexibility to earn and use your points, both cards have some serious travel perks like: rental car collision coverage, baggage delay insurance, emergency evacuation and medical insurance, lost luggage reimbursement, trip cancellation insurance, etc.

The Chase Sapphire Reserve also comes with an annual $300 travel credit, Global Entry or TSA PreCheck fee credit, access to over 1300 airport lounges around the world, and credits and membership perks for brands like DoorDash, Instacart, Peloton, and Lyft.

But let’s talk about cost. The Chase Sapphire Preferred has a pretty standard $95/year fee which is 100% worth the perks.

The Chase Sapphire Reserve has a $550/year fee which is…a lot. But let’s break that down. Remember, the Reserve comes with a $300 annual travel credit which immediately drops that to $250/year. So then you just have to decide if the increased point rewards, complimentary Global Entry/TSA PreCheck, lounge access, Instacart subscription, Doordash subscription, AND all of the travel insurance add up to the remaining roughly $150 in price difference between the Preferred and the Reserve.

All of the math suggests that it does, but it will just come down to if you’re comfortable with a card with such a high annual fee.

Whichever of these two cards you choose, here’s how I use the points:

Unless I’ve just opened a new card and I’m working to meet the spend requirement to get the sign up bonus (i.e. get 60K points when you spend $4000 in the first three months, etc.), I put all of my daily purchases on my Chase Sapphire card.

Then depending on what travel I’m looking to book, I either 1) Transfer Chase points to Southwest to book airfare, 2) Transfer Chase points to Marriott to book hotels, or 3) Book hotels through the Chase travel portal.

The Chase travel portal gives your Chase points a dollar value (1.5 cents for the Reserve and 1.25 cents for the Preferred) and you can use your points against the cash value of a LOT of different hotels.

I really like using this option to book luxury hotels like the Four Seasons or Auberge which don’t have a credit card/loyalty program to collect rewards on.

For example, let’s say I have the Chase Sapphire Reserve card (1.5 cents/point value) and I have 400K Chase Ultimate Reward points saved up. That’s a cash value of $6000 that I can use to book a resort through the Chase travel portal.

If I have the same number of points but I have the Chase Sapphire Prefered card (1.25 cents/point value), that’s a $5000 value.

Use >>this link<< to get 60,000 bonus points when you sign up for this card.

Multi-Card Strategy

Points REALLY start to snowball when you start stacking cards to maximize rewards. The three cards I’ve mentioned above all work together really well since Southwest and Marriott are partners with Chase.

You can collect the sign up bonus (and program loyalty points) with the Marriott Bonvoy Boundless card and have the option to move your Chase Ultimate Rewards points over to Marriott Bonvoy too.

And the same for the Southwest/Chase Sapphire combo. Get the sign up bonus from the Southwest Premier Rapid Rewards card and you can transfer Chase Ultimate Reward points to your Southwest account.

Depending on how many cards you want to manage, you could also add World of Hyatt and United cards to your lineup and everything will still pair well with your Chase Sapphire.

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.

P.S. Thanks for sticking around and reading this whole post! If you have ANY questions about planning your trip to Hawaii, you can join my free Facebook group here. I’m there answering questions every day and there are 7500+ other friends who have a ton of Hawaii information to share!

Also, if you want to follow along on my travel adventures in real time, you can follow me on Instagram (@caitylincoln). My post captions are full of travel tips and I have a ton of story highlights and videos with great info. And please share my account with your friends that are headed to Hawaii! Your support really helps me keep this blog running!