A family of four's week on Maui for 195k points and $1,717, using two credit cards

If you spend any amount of time in the points and miles family travel world, you will hear an influencer talk about how they took their whole family to Hawaii for basically FREE. But when you search for flights, you're utterly confused on how they're affording it.

Because even with points and miles, it's not cheap!

Well here's how they do it, friend: Two cards, two Companion Passes, and one kid who still flies in my lap. 😎

That combination wrote my ground rules before I ever opened a search window:

• Fly Monday, not Saturday.

• Position out of Las Vegas (LAS).

• Two real home bases, not four.

And do NOT try to knock out the road to Hana in a single day.

The ground rules

Refresher on the challenge: four travelers, the whole trip inside a fixed window over Thanksgiving week, and a budget of 200,000 points and $2,000, with points from a maximum of three credit cards.

I used two.

A Southwest co-branded card, and what's clearly becoming my ride or die card for travel. Another one that transfers to Hyatt at a great ratio.

The Southwest card is the one doing the heavy lifting here, so let's start there.

What the cards actually unlock

Step 1: Hold a Southwest co-branded card like one of these.

By having a Southwest card, you no longer have to pay for a bag (since they so kindly took away free bags), and you can choose your seat prior to check-in even for a basic fare flight, though when you can choose your seat varies based on the tier you pick.

Step 2: Earn a Companion Pass

This is where Southwest outshines the competition, and it's also how influencers are taking their whole family to Hawaii on points.

There are different methods to earning a Companion Pass, typically involving spending a certain amount each year or earning a certain amount of points/flights flown.

BUT, occasionally Southwest runs promos to earn a Companion Pass very easily.

For instance, there was one recently to earn a pass after booking and flying a flight during the designated window. The pass was only for a short period of time though.

With the way Southwest has been shaking things up lately, you never know what they're gonna throw out there.

I happened to take advantage of a companion pass promo earlier this year and opened a Southwest card and have been putting that bad boy to WORK.

So, in this case, we're going to assume I have a Southwest co-branded card and a companion pass... cause I do. 😎

The flights: four people to Maui for 90,000 points and $44.80

So, in what we can call my signature move of breaking the rules a little, we're going to save some points by flying out on Monday, the 23rd. We're also flying out of Las Vegas.

2 reasons: it's a direct flight (or there's a good chance your connecting flight would layover here) and it's cheaper.

For a family of 4, there are two ways to save big on these flights.

Option 1: Two adults in your household hold a companion pass so two people can fly for free (+ taxes)

Option 2: One of your children is still under 2 and is therefore a lap infant and flies free of charge (you just have to hold them the entire flight 😬)

I actually fall in BOTH categories, as my daughter is under 2 and my mom actually has a companion pass as well.

Assuming two adults have a companion pass, I'd purchase the following Southwest flights:

Harry Reid Las Vegas International Airport (LAS) to Kahului (OGG) on November 23rd for 23,000 points and $5.60 per person. 👇

And the return flight on November 30th for 22,000 points and $5.60 per person. 👇

Now, these are by no means the most luxurious flights. It's Southwest, so expect a couple snacks and a soft drink with their standard leg room.

BUT, with 2 companion passes you can save on airfare for 2 people in your party.

So in total, it would come out to 90,000 points and $44.80 round trip for 4 people.

That's 22,500 points and $11.20 per person, over Thanksgiving week, to the middle of the Pacific.

Home base #1: one night by the airport

Now that I've cheated my way to the islands, here's where I'd stay.

I'd actually book the first night at the Courtyard by Marriott Maui right by the airport. And I'd pay cash.

Why? Well the points rate was way overpriced and staying by the airport puts me in the perfect position to wake up early the next morning for the adventure that I have planned.

One night, $358. 👇

So, I'd land the first night, pick up the rental car, find dinner, and stock up on some snacks for the week we're in town. (Hawaii is expensive, but they do have Costco 😉)

We'd all turn in early and sleep off the travel day.

Home base #2: two nights in Hana

The next morning, I'd get everyone up as early as I could manage and take off on the drive to Hana.

Now, a lot of people do the road to Hana in one day but with stops that can amount to a 10-12 hour day. No thanks.

We're going to take our time, enjoy the sights, stop for banana bread along the way.

Because we're staying in Hana for two nights.

The Hana-Maui Resort is a secluded property in Hana town that puts you right in the heart of some of the best the island has to offer.

It's bookable with World of Hyatt points which was my plan but there's an 80th anniversary cash rate currently that was actually a better deal than booking with points.

Two nights, $846. 👇

I'd either book two queens OR spring for the bungalow option for more space to spread out since there are four of us, if there's room in the budget.

By spending 2 nights in Hana, you don't have to rush along the drive or fight traffic to get back before dark – which matters in November when the sun sets earlier.

Instead, we can take our time, plan some hikes, visit waterfalls before they get crowded and enjoy a couple sunrises and sunsets in Hana.

Note: after our stay there, we'd pack up and head back the way we came. The back side of the island is a rougher drive, not for the faint of heart, and rental insurance is often voided by the unpaved roads.

Home base #3: four nights on points

The rest of our trip is going to be spent relaxing at the opposite end of the island at the Hyatt Regency Maui Resort and Spa.

While there are certainly fancier options, this resort is highly regarded as a GREAT option for families with kids.

Multiple pools, beach access, kayaking, and daily activities to take part in during your stay.

Standard rooms run between 20k-45k a night post-Hyatt award chart overhaul.

And for the dates I was looking at, it would cost 105,000 points for a standard two queen room for 4 nights. 👇

That's 26,250 a night for all four of us in one room, at the top end of the standard range, during the busiest week of the year.

After 4 nights there, we'd pack up and begin the long trek back home.

About playing (cough, cough) fast and loose

Maybe this is playing a little fast and loose with the rules as far as this assignment goes, BUT it is exactly how I would book this trip. The Companion Pass wasn't something I manufactured for a challenge.

I already had it.

The damage

Here's the bill:

Points: 90,000 (Southwest flights) + 105,000 (Hyatt, 4 nights) = 195,000

Cash: $44.80 (flight taxes) + $358 (airport hotel) + $846 (Hana) = $1,248.80

Rental car: Using Costco travel: $468 for a mid-size SUV for the week

Two cards. Seven nights. Four people. And $283 of the $2,000 never left the account.

What else I looked at

• Points at the airport hotel. Way overpriced for a one-night crash pad. Cash won, and it wasn't close.

• Hana-Maui on World of Hyatt points. This was the original plan. The 80th anniversary cash rate beat it, so I paid cash and kept the points for the back half of the week.

• The road to Hana in a single day. 10-12 hours with stops. No thanks. 🤷‍♀️

• The back road out of Hana. Shorter on a map. Rougher in practice, and often enough to void your rental insurance.

• The bungalow at Hana-Maui. More room for four people, more money. Worth it if your cash budget has the room; mine did, barely.

The bottom line

Is 195,000 points and $1,717 a lot for a week on Maui? For one or two people, yes.

For four, split across two Companion Passes and a lap infant, it's about $429 a head for seven nights and round trip airfare during the single most expensive travel week of the year.

The flights are the whole trick. Once four people get to the islands for 90,000 points and $44.80, the rest of the week gets easy.

And if you don't have a Companion Pass, take the other half of this itinerary anyway: one night by the airport, two nights in Hana so the drive isn't a death march, and four nights somewhere with a pool the kids won't get out of.

Plus, if I can hang loose anywhere, it's gotta be on a beach in Hawaii, right?! 😉