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

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 All Things Travel Mom Squad: stan.store/travelmomsquad

Links For This Episode: 

• How to Take Your Family to Hawaii for Nearly Free: Family Guide to Hawaii on Points & Miles -https://travelmomsquad.ck.page/products/hawaii-family-guide 
• Shaka Guide: Kauai Tours | Audio Tour Guide - https://www.shakaguide.com/tours/kauai 
• Reservations for Kalalau trail: Reservations - Go Hāʻena - https://gohaena.com/
• Pineapple Express car rental: https://pineappleexpresskauaicarrentals.com

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