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Points Talk with the Travel Mom Squad

113. Inside Our Hawaiian Holidays – How We Spent the Holidays in Hawaii on Points and Miles

Points Talk with the Travel Mom Squad

Alex, Pam and Jess

Places & Travel, Education, Society & Culture, How To

4.9 • 734 Ratings

🗓️ 28 January 2025

⏱️ 69 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

The holidays are magical no matter where you celebrate, but spending them in Hawaii? That’s next-level. In this episode, the Travel Mom Squad shares how we used points and miles to pull off unforgettable trips to Maui and Kauai over the Christmas and New Year holidays. We’re giving you all the behind-the-scenes details so you can start planning your own Hawaiian holiday adventure. 

Maui with Alex’s Crew
Alex starts by sharing how she surprised her family with a Christmas gift they’ll never forget: six nights at the Hyatt Regency Maui. Planning a year ahead made all the difference, allowing her to lock in the best rates using 210,000 Hyatt points for two king rooms. Alex breaks down why booking early is crucial during peak season and how transferring points to Hyatt made this dream trip possible. 

Pam’s Anniversary Upgrade Quest
Pam recounts her experience booking alongside Alex and attempting to score a suite upgrade using Hyatt’s upgrade award. While she didn’t get the full upgrade she hoped for, Pam shares the hilarious story of how a mix-up led to Alex receiving flowers meant for Pam’s 50th wedding anniversary. 

Kauai Adventures with Jess
Over on Kauai, Jess’s family enjoyed six nights at the Grand Hyatt Kauai, covering two rooms with a whopping 420,000 Hyatt points. Jess explains how she maximized her points strategy by leveraging Hyatt’s Guest of Honor program and sharing tips for making family stays more enjoyable. 

Flights and Rental Cars: Navigating the Holidays
Booking flights to Hawaii during peak season can be daunting, but we share how Pam's experience was flying United and how Jess and Alex got creative with Southwest companion passes, gift cards, and points to keep costs down. Jess also shares her game-changing experience renting a car with Pineapple Express on Kauai—a rental-car service that lets you skip the lines and even includes beach gear!

Hawaiian Holiday Takeaways
The best part of these trips? Spending time with family and meeting some of you, our listeners, who were also in Hawaii thanks to points and miles. Whether it’s taking the grandparents along, planning a holiday surprise for your kids, or just soaking up the aloha spirit, this episode is packed with inspiration for your next adventure.



Links:

Links For This Episode: 

 

Episode Minute By Minute:

  • 00:00 – Intro: How we each spent the holidays in Hawaii
  • 01:30 – Alex’s Maui trip: Booking the Hyatt Regency and family surprises
  • 07:00 – Pam’s story: Anniversary upgrades and club lounge tips
  • 15:20 – Jess’s Kauai trip: Guest of Honor perks and family fun
  • 23:30 – Flights: Southwest companion passes and creative savings
  • 31:45 – Rental cars: Tips for Maui and Kauai
  • 41:00 – Reflections: Meeting listeners and making memories

 

Transcript

Click on a timestamp to play from that location

0:00.0

Ever dream of taking your family on a dream Hawaiian vacation during the holidays?

0:04.6

If so, listen in as we recap how we did just that for our families and how you can do it too.

0:10.2

Welcome to Points Talk with the Travel Mom Squad.

0:13.1

We are three moms who've discovered how to leverage credit card welcome offers to get hundreds of thousands of dollars of travel expenses for nearly free.

0:21.6

We've used credit card points of miles to take vacations to places like Hawaii, Paris, Greece,

0:26.9

Maldives, Japan, and so much more.

0:29.5

And the best part?

0:30.7

We each still have 800 plus credit scores.

0:33.7

Imagine being able to take the vacation of your dreams for nearly free.

0:37.4

It's totally possible and we're here to show you how.

0:41.2

Hey, I'm Alex. And I'm Pam, Alex's mom. And I'm Jess. Let's Talk Points. So we all just recently returned from spending some of the holiday break in Hawaii. Alex and Pam and Alex's family of six were

0:57.2

on Maui at the Hyatt Regency Maui. And then me and my blended family of six were on Kauai at the Grand

1:05.1

Hyatt, Kauai. Obviously used points and miles for the vast majority of our flights and hotels for this trip.

1:13.0

So let's get into how we each made this happen.

1:16.0

So Alex, kick it off with how you booked the higher Regency Maui for eight people for $0.

1:24.1

Well, I mean, I had technically booked it for four and then my mom booked it for four. I didn't book it for everybody. But yeah, this was really exciting. So last December, so December 2023, the three of us were in Arizona at our retreat. And I don't even know how it came up, but just decided let's go I'm going to take my family to

1:46.3

Hawaii next year for Christmas I'm going to surprise my kids with a trip so every year for

1:51.0

Christmas we do a family gift so one year it was like a double shot from Costco you know like the

1:55.8

basketball double shot game one year it was like a bounce house for the basin so like you know

2:00.6

the little

2:00.9

Fisher Price ones when they were really little. So every year we try to do a fun gift like that.

2:04.5

I think one year we did a ping pong table. And this year I was like, we're going to do a trip to

...

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