Our family of 5 visited Maui in March of 2023. Unfortunately, in early August 2023, a series of wildfires broke out on the island of Maui causing widespread damage, killing at least 100 people and leaving four persons missing in the town of Lahaina on Maui’s northwest coast.

In October 2023 Maui reopened to tourists, and with an economy heavily dependent on tourism, I’ll now be sharing the details about our trip, while updating as best I can what is currently open/closed.

Best flights to Hawaii with Kids

As per usual, we flew on Southwest using our Southwest Rapid Rewards points and our two Companion Passes. You can read more about how to earn a SW companion pass (or two) in this post. There are a lot of flights from the west coast to Hawaii across most airlines, and we’ve also flown Hawaiian Airlines and had an excellent experience.

Best Hotels in Maui with Kids

We stayed at the Hyatt Regency Maui Resort and Spa. As a heads up, even at 10pm it took us about an hour to get from the airport to the hotel. The resort, which opened its doors again on November 1, 2023 after housing displaced locals after the fires, has an amazing open air lobby (there are no doors!) and an incredible ocean view. To book on points, room rates range from 25-35K Ultimate Rewards points a night and we snagged a room with a partial ocean view and balcony.

Although we decided against the luau due to its steep price ($210 for an adult!), the breakfast buffet was one of the best we’ve ever had. It had an amazing array of choices, with the chia pudding and the fresh lychee being the standouts for me. The resort also offers scuba classes and a stargazing tour, “Tour of the Stars,” which became one of our favorite activities, offering us the ability to see stars not visible from the continental United States.

The resort is perfect for families, offering fantastic pools that cater to all ages – there is a kids pool, plus an adult pool but unfortunately the Grotto that connects both of them has since been closed for structural issues with no plans to reopen it.

They served this drink at the pool that was made from the purple sweet potato Ube (it was called Ube-bay, like oooh baybay), and it was delicious. The hotel also has penguins that live in its lobby along with koi fish, and every morning at 9am you can join them for feeding time. This definitely added a unique touch to our stay.

Best Things to do in Maui with Kids

Our Maui adventure wasn’t confined to the resort and we actually got to see quite a bit of the island’s natural beauty and culture through various activities:

Jungle Zipline: An exhilarating zipline experience through the treetops of Maui, and we were able to bring our 9 year old son to zipline with us! The little two stayed behind with grandma and grandpa.

Whale Watching Tour with Makai Adventures: They unfortunately lost their flagship boat during the fires but have since purchased a new one and are up and running for business. This tour was incredible, the boat is small with a max occupancy of 20 people, and we saw so. many. whales. The guides were very knowledgeable and also showed real care for the whales themselves, and it was one of my favorite things on our entire trip.

Surfing Goat Dairy: A quirky and delightful tour in Kula, where you can even milk goats during an evening tour. We did a goat cheese tasting, fed the goats, and since Kula is more inland and up in the mountains we got to experience incredible Maui views from a new vantage point.

Kapalua Bay Beach: Perfect for the kids with calm waters and the opportunity to hike the Kapalua Coastal Trail. We rented an umbrella and some beach chairs along with snorkeling equipment. Snorkeling here was magical; we saw a ton of brightly colored fish and several sea turtles up close.

Tour of the Stars (at the Hyatt Regency Maui): I know I mentioned this above, but we really enjoyed it and thought it was worth a bit more info. This activity does cost extra (I think it was around $40-50 for adults?) – you meet in the hotel lobby and then are led up the stairs to the roof of the hotel where a former NASA scientist has these incredible telescopes set up to view different constellations around the night sky. He was incredibly informative, and you can ask any questions you’d like.

The Road to Hana with Kids

If I’m being perfectly honest, I don’t think I would do the Road to Hana again with younger kids. It is a beautiful drive and there are a lot of cool stops and things to see, but younger kids often don’t appreciate stuff like pretty scenery or lava tubes, ya know? Plus the roads are very windy, and our kids don’t get carsick often but two of them were pretty nauseous by the time we headed back. If you do want to go and bring your kids, here are my tips:

• Plan to leave early. Just the beginning of the Road to Hana was already a full hour from our hotel.
• Download the Shaka Guide and pay the $20 or whatever it is for the guide – it’s GPS enabled and it’s amazing for understanding what you’re seeing and knowing where to stop. We would have absolutely missed the entrance to the Lava Tube without it!
• Bring a lot of snacks and activities for the kids to do in the car because you’ll be spending most of the day in there.
• Bring Kids Dramamine and also the kids nausea bracelets.
• Stop and get some banana bread – there’s a bunch of places to get it along the way
• Get out and hike once or twice to break up the day. We hiked at Twin Falls (2nd stop, but we did it on the way back). As a heads up, it was described as a “short hike” to the waterfalls (which are small) but I felt like it was a fairly long walk. Potentially because our 6 year old cried the entire way.
• Make a reservation for the Black Sand beach – we did not do this and were unable to enter.
• If you’d prefer to take it slow, staying a night or two at the Hyatt in Hana might be a good way to break up the drive a bit.

While we didn’t make it all the way to the Seven Sacred Pools (we got a later start and the kids were over it) we did really enjoy all the scenery along the way. It is beautiful, and yes the roads are windy and tight in spots. If you’re a beginner driver, this might not be for you. At one point I could put my hand out the car window and touch the wet moss on the side of a ravine.

Best Restaurants in Maui with Kids

These are the places we ate and enjoyed. We never felt out of place with our kids, although if you’re aiming for more upscale places, or want a confirmed table if you have a larger party, I would highly recommend making reservations several weeks to even months out for some places. Mama’s Fish House was highly recommend but they book up months in advance so we weren’t able to get in.

• Kihei Caffe Lahaina – incredible breakfast, we came here multiple times
• Leilani’s on the Beach – great for a casual dinner right on the water. Outside seating only.
• Leoda’s Kitchen & Pie Shop – excellent sandwiches (they’re huge) and yummy pies! Great stop for lunch after leaving Kula and heading back into Lahaina.
• Down the Hatch – TEMP CLOSED – Excellent seafood, we also came here multiple times – the Lava Lava Shrimp is incredible.
• Paia Fish Market – TEMP CLOSED – fish and chips
• Ululani’s Shaved Ice – TEMP CLOSED – best shaved ice we’ve ever had, we came here 3 or 4 times during our week trip!
• 808 Grindz – TEMP CLOSED – delicious home cooked breakfast, ran by a family, be prepared to wait (but worth it)

If you’re looking for information on what is open since the fires, I have found this website to be a good resource.

As Maui rebuilds, the spirit of Aloha has never been more important. Visitors are encouraged to extend grace and support to the local communities, contributing to the island’s recovery through mindful tourism.

Mahalo.

What is the Southwest Companion Pass?

The Southwest Companion Pass allows you to choose one person to fly with you, free of airline charges. You still pay taxes, which for domestic flights are $5.60 per leg, but you can use the pass unlimited times whenever you purchase or redeem points for a flight as long as there is a seat available on that flight. There are no blackout dates.

To earn the companion pass, you can either fly 100 qualifying one-way flights or earn 135,000 qualifying points in a calendar year. Once you earn the pass, you’ll have it for the remainder of the year in which you earned it, plus the following full calendar year. You can also change your companion up to three times per calendar year.

How to earn the Southwest Companion Pass (or two of them)

I can assure you that we did not fly 100 flights – instead, we each opened 2 Southwest credit cards and the signup bonuses were enough for us to each earn a Companion Pass. In my opinion, this is what makes Southwest the most affordable airline for us. If we only had one, it just wouldn’t be as beneficial. Then, we each designate one of our children as our companion. When we go away for a long weekend just the two of us, one of us calls Southwest to change our companion to the other and voila – 2 flights for the price of one.

How to maximize the Southwest Companion Pass:

If you want to really maximize the pass and get the most out of it (aka have it for the longest amount of time) then the best time to start opening the cards is going to be end of October or anytime in November of any calendar year. This table shows the exact cards we opened, the exact dates we opened them, and the amount of bonus points we got for each:

Player	Card Opened Date	Cards Opened	Sign up Bonus	Points Earned with dates
Raya	October 14, 2022	Southwest Rapid Rewards Performance Business card	80,000 points	January 2023
Raya	December 1, 2022	Southwest Rapid Rewards Plus card	50,000 points	January 2023
Duane	November 1, 2022	Southwest Rapid Rewards Performance Business	80,000 points	February 2023
Duane	January 20, 2023	Southwest Rapid Rewards Plus card	50,000 points	February 2023

I earned my Companion Pass January 18, 2023 and Duane earned his in February. We used them to take our family of 5 to Maui in March!

If you notice in the table above, we made sure to earn all of our points in Jan/Feb of 2023. This is very important because all 130,000 points need to be earned in the same calendar year in order to achieve the companion pass. I cannot stress this enough, and every year so many people make the mistake of earning their sign up bonuses too soon.

One other thing to note – all the credit cards listed above have varying annual fees. The strategy here is to, yes, pay the annual fee for the first year. The value you’ll get from the points and the Companion Pass(es) will greatly outweigh the annual fees. Some of the cards also have additional benefits like a reimbursement for Global Entry/TSA Precheck that can offset the cost too. Once your first year anniversary hits and the annual fee posts for the second time, you have 30 days to cancel your card and get the annual fee refunded back to you. This is what we have done and will continue to do. It is not recommended to cancel any credit card before first having it for an entire year.

Now that you’ve got the gist, there is a bit of nuance to this process, and it’s important to pay attention to the details in this situation.

Here’s what else you need to know:

Southwest currently has 5 available credit cards – 3 personal and 2 business cards. You can only hold one personal card at a time, which means your strategy here needs to be either opening 1 personal and 1 business card, or opening two business cards.

All 5 of the Southwest cards are issued by Chase, so that means that you need to be under 5/24 in order to apply for all cards. If you are cutting it close at 4/24, I would do one of two things:

1. Open the business card first (because you need to be under 5/24 to get approved for a chase business card) and then open the personal card at least 30 days later. The personal card will use up your last 5/24 spot, so you have to be ok with giving that up.
2. Skip the personal cards and just open both business cards and keep yourself at 4/24.

Pay very close attention to the minimum spend on each card, and leave yourself at least a $500 buffer on the card (meaning spend at least $500 under the minimum spend required to get the bonus points) and then put the card away until after January 1st. Do not put any recurring charges on this card, do not give it to a partner or spouse. Once January hits, go crazy, spend the rest of the money to meet the minimum spend and earn your points.

It’s very important to note that returns will still count towards your minimum spend. This means if you buy something that puts you over the minimum spend, and then return it (even if it’s returned immediately), you are likely going to earn your points early. (Note: this is not a hack to get points without actually meeting the minimum spend as there is a chance the bank could take away your points).

What happens if I screw up and earn my points before the end of the year?

Well, you have a couple options.

Option 1 – you can hit the minimum spend on your second card before the end of the year and still earn the companion pass for one year at least.

Option 2 – if you were originally planning to do 1 personal and 1 business card, then you could open up the second business card (you can hold 2 biz cards at once, just not 2 personal cards) and continue with the original plan to meet the minimum spend on both cards after January 1st. Alternatively, if you already opened 2 biz cards and no personal cards, then you could apply for one of the personal cards (assuming, again, you’re under 5/24).

The best part about the Southwest Companion Pass, besides 2 flights for basically the price of 1, is that once you’ve earned the 130,000 points to unlock the companion pass, you still have those points you can use to book flights! You do not have to use those points to “buy” the pass, per se. So if you have 2 people getting the companion pass, that amounts to 260,000+ points to book flights for your family! It’s really incredible.

Why can’t I choose my seats on Southwest?

Sometimes Southwest gets a bad rap because it’s the only airline where there are no assigned seats. While I understand this can be stressful for some families, I can assure you it’s not that bad. Southwest does boarding in groups – at checkin you’ll be assigned either Group A, B or C. Group A goes first. Then B, then C. I do recommend setting an alarm and checking in immediately at the 24 hour mark prior to your flight time. In our experience, our kids who have the companion pass each get assigned the number right before ours during checkin, even when they check in hours later. So, for example, if I check in and get B55, and then I check in my companion, my companion will get B54.

After the A group boards, they will do family boarding. The SW rules state that if you’re traveling with a child age 6 or younger, you’re eligible for family boarding. However, in our experience (and according to other data points from recent travelers, including this article from The Points Guy) any child up to age 13 will be allowed to board during this time. This has been our experience each time we’ve flown Southwest – and if you board after Group A, there are still plenty of seats available for a family of 5 like ours to sit together.

Is Southwest Companion Pass worth it?

If you’re planning trips to any of the places Southwest flies, then the Southwest Companion Pass is an absolute must. It makes air travel for larger families much more affordable. Not to mention, when booking with points you can cancel a flight up to 10 minutes prior to departure and get all your points back. This is an amazing feature if you have kids who get sick at the drop of a hat (isn’t that all kids?). And each passenger (including companions) get 2 free checked bags on every flight! All these benefits are a testament to the incredible value and flexibility that Southwest offers to its loyal customers, making it an unparalleled option for those families looking to maximize their travel benefits without compromising on the quantity or quality of their trips.

There are some parts of traveling that can feel very overwhelming, especially when you include all of the planning and logistics that need to happen leading up to a trip. I had been putting off getting passports for our kids because once you get them, they are only good for 5 years (versus 10 years for adults) and they are not cheap. It never made sense to do it until we had a set trip planned. Finally at the end of last year we had to bite the bullet as we were planning our first trip outside of the country for early 2024 and wanted to ensure we allowed enough time for processing. At the time, processing times were 12-16 weeks although they seem to have shortened since then. Additionally, there were a couple of things that caught us by surprise even though, once I thought it through, they make perfect sense.

Those two things are:

1. You must go in person to apply
2. Both parents (if listed on the birth certificate) must be present in person

I had planned to apply for the kids passports just like I did my own – get photos taken at Walgreens, fill out and print the applications and mail them off with the appropriate documents. But while I was trying to find instructions on how to mail them in, I realized my only option was to schedule an in person appointment. And that’s when I realized this needs to be done in person, and that my husband also needed to attend. Was it inconvenient to get all 5 of us in the same place at 3pm on a Thursday between everyones work and school schedules? Yes, it absolutely was. But does it make sense to me that, in order to get a legal document authorizing my child to leave the country, this needs to happen in person with the consent of both parents? 1000% yes.

The state department does a really good job of laying out exactly what you need to complete this process and this website right here should be your Bible when applying for a passport: Applying for a Passport for a Child Under age 16. I would recommend first making your in person appointment because, at least here in Arizona, the first available appointment for 3 kids was 6 weeks out. Perhaps it would have been sooner with only 1 or 2 kids?

Once you have the appointment set, read through the above linked site several times as you’ll need to be very detail oriented to ensure you don’t forget anything. Our children are all US citizens and we are both listed on the birth certificate so our situation was fairly straight forward. Here’s what we brought to our appointment in Arizona (but again, please refer to the link above to confirm what you’ll need for your specific situation):

• Our photo ID’s
• Application for each child (typed, not handwritten if possible to prevent errors)
• birth certificate for each child PLUS a copy of each birth certificate for each child (yes, you need to send in their original birth certificate and a copy. They will mail the original back to you, but it will be sent separate from the passport)
• passport photos for each child (got ours at Walgreens)
• A separate check for each child’s passport fee – this will be mailed in with their application – PLUS $ (a credit or debit card) for the processing fees which are charged day of appointment)

Despite being ultra prepared with paperwork, we did have one hiccup in that during our appointment. The woman who helped us thought that 2 of our 3 kids’ passport photos would be rejected. So she recommended that we drive back to the place we had gotten them taken (like 2 months before, mind you) and have them redone. So my husband went back to work and I traipsed all three kids back to Walgreens, had the photos redone, and then went all the way back to the passport office with all three kids in tow. As a side note, keep your receipt because Walgreens redid them at no cost to me.

She mailed everything off, handed me a receipt and told me how to track the progress, and sent us on our way. It was roughly 4 weeks from our appointment date to the day I received all the passports in the mail, which was a very quick turnaround. While we did not pay for expedited service, you can certainly do that if you have a trip rapidly approaching. I also would not assume that 4 weeks is the norm and would allow for extra time (6-12 weeks) just in case.

Overall, the process of obtaining passports for a child (or three) though initially overwhelming, was a fairly easy process that I’m sure we will appreciate even more as we explore Costa Rica in a couple of months! And now, with passports in hand, our family of five is now ready to embark on more exciting global adventures in the future. In fact, we are already starting to plan 2 big international trips for 2025. Hope you can join us for the journey!

A brief backstory – We have been travel hacking “seriously” for about a year and a half and we’ve been to Maui, San Diego, Oceanside, San Francisco and most recently Washington DC! But going back in time, I actually took my first “free” flight in 2018, and I went to Bali. I had purposely opened up a card for this exact reason, and used all my points on one flight. I booked my flights through the Chase portal because, at the time, I didn’t know any better (this is not the best value for your points). But I still got to Bali (and home) completely free. And got a 24 hour layover in Hong Kong too!

Before jumping into actionable steps, it’s important to prioritize responsible credit card usage when engaging in this hobby. We strongly recommend that if you currently have credit cards that you’re paying off, do that first before you start. You’re not getting free travel if you’re paying interest on a credit card balance.

Step 1 – Figure out your credit score

You want at least a 640 to start, and the higher the better. Sites like Credit Karma are ok for checking your score but in our experience, Experian Boost is the best one and it’s the one we use. You can create a free account to check your score and you can see the “ingredients” of your credit score.

Step 2 – Figure out what your 5/24 status is

The Chase 5/24 rule is a Chase rule that states that if you have been approved for five or more personal credit cards in the last 24 months, you will automatically be denied for any additional Chase credit cards. This includes all credit cards, not just Chase cards. So if you signed up for a JC Penney card last year, or a Discount Tire card like we did before we knew better, that card counts as one of your five cards. This is why it’s often recommended to start with Chase cards – because you’re starting the 24 month clock and the hope is by the time you’ve run out of Chase cards, you can move on to Capital One and American Express cards, neither of whom have this 5/24 rule. And then in 24 months you can move back to Chase, and so on.

Step 3 – Figure out your monthly spending (that can be put on a credit card)

This one might seem kind of silly, but let me explain why it’s important. Each credit card you sign up for is going to have what’s called a “minimum spend” requirement. This is the minimum amount you need to spend on that card in order to receive the sign up bonus (often called a SUB) and there is usually a specific timeframe in which you need to hit that minimum spend. Most commonly it’s 90 days, but not always – I’ve seen 60 days or 180 days on some cards.

So not only do you need to know how much you’re spending to know if you can hit the minimum spend, the goal here is to not spend any more money than you would without the credit card. So knowing your usual budget is a good way to keep yourself in check and ensure you’re not overspending.

Step 4 – Not all points are created equal

Recognize that not all points have equal value, and different ecosystems act as distinct currencies. For instance, compare Marriott and Hyatt points – You can transfer your Chase UR points to both Marriott and Hyatt – but it’s often not the best value to transfer them to Marriott. This is because 1 Marriott Point holds less value than 1 Hyatt point. So for example, you can get an average run of the mill Marriott for 50K Marriott Points a night but for 35-45K you can book a Park Hyatt, which is the highest tier super luxury hotel for Hyatt.

I’m not saying one is better than the other, but I’m saying it’s important to know the value of the points you’re wanting to use. As far as redemptions go, a good Marriott point redemption is about 0.8 cents per point, and a good Hyatt point redemption is 2 cents per point or more. Don’t get overly concerned about point values initially; it becomes easier over time to discern good values with practice. Ask yourself if a redemption aligns with your family’s needs and brings joy; if yes, book it without worrying about the point value.

The other thing that’s important to understand, is that there are two main categories of points. There are flexible points, and airline/hotel specific points (these are called cobranded cards).

Let’s start with the flexible points – some of the more popular ones are: Chase Ultimate Rewards Points (UR), Capital One Points, and American Express Membership Rewards (MR) – think of these points as a flexible currency that can be transferred to different transfer partners. A transfer partner is a hotel or an airline that accepts these points as a form of payment. So, for example, I open up a Chase credit card and I earn 60,000 Ultimate Rewards points. I can then transfer those 60,000 Chase Ultimate Rewards points to places like Southwest Airlines, United, British Airways, Hyatt, and so on to book a hotel room or a flight.

The second main category is going to be cobranded cards that are specific to that airline or hotel chain. For example, you can open a Southwest Rapid Rewards credit card and earn, let’s say 60,000 Southwest Rapid Rewards points once you hit the minimum spend. These points can only be used to book flights on Southwest Airlines, you cannot transfer them anywhere else. Almost every airline and hotel chain has their own are cobranded cards and they all earn points that can only be used for that specific airline or hotel.

Step 5- Choose your first credit card and open it!

If your credit score exceeds 640, you’re under 5/24, and you can meet the minimum spend, consider opening a Chase Sapphire card, widely recommended by travel hackers for its benefits and features.

There are 2 Chase Sapphire cards – the Preferred and the Reserve. Check out the table below to review the differences between the cards. You’ll need one of these 2 cards in order to transfer your Chase Ultimate Rewards points to any transfer partners.

Chase Sapphire Preferred

Chase Sapphire Reserve

Annual Fee: $95 Annual Travel Credit: $50 (must book thru Chase portal) Auth user fee: $0 Foreign Transaction Fee: $0 Travel Insurance: Auto​ Rental Collision Damage Waiver, Trip Delay Reimbursement, Lost Luggage​ Reimbursement, Trip Cancellation/Interruption Insurance. Rewards/Bonuses: 3X points on dining, 2X points on travel

Annual Fee: $550 Annual Travel Credit: $300 (just has to code as travel) Auth user fee: $75 Foreign Transaction Fee: $0 Travel Insurance: Auto​ Rental Collision Damage Waiver, Trip Delay Reimbursement, Lost Luggage​ Reimbursement, Trip Cancellation/Interruption Insurance. Rewards/Bonuses: 3X points on travel and dining Airport Lounge Access: Complimentary Priority Pass membership TSA PreCheck/Global Entry credit: up to $100 reimbursed every 4 years

Jumping into the travel hacking arena calls for a thoughtful and strategic approach, as we shared above. By starting with a clear understanding of your credit score, navigating key rules like the Chase 5/24, and evaluating your monthly spending habits, you can start to maximize the benefits of credit card points for almost free travel and the Chase Sapphire card is an excellent starting point. If you’ve been confused about where to start in the exciting world of travel hacking, we hope this has been helpful. We’d love to hear where you’re going on your first trip. Happy travels!