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

Feeling overwhelmed by points and miles? You’re not alone! In this inspiring episode, we sit down with Devon Gimbel of Point Me to First Class to discuss the psychology of learning points and miles—and why you’re probably doing better than you think. Whether you’re new to the game or feeling stuck, Devon shares her expertise and encouragement to keep going.

Devon’s Journey: From Skeptic to Expert
Devon begins by sharing her personal journey into points and miles. Growing up in a single-parent household, travel was often limited to road trips and camping. And Devon didn’t dive in immediately—she was skeptical of credit cards and their potential for debt. Slowly but surely, she learned how to responsibly leverage points and miles, and her first intentional redemption? Flying Lufthansa First Class to Paris!

The Four Phases of Learning Points and Miles
Devon introduces the “four phases of learning” and how they apply to mastering points and miles:

1. Ignorance is Bliss: At the start, you don’t know what you don’t know, and every little win feels huge.
2. The Valley of Despair: Confidence takes a hit as you realize how much more there is to learn, but this phase is key to growth.
3. Conscious Competence: Skills and knowledge improve, though it still requires effort to apply them.
4. Unconscious Competence: With time and practice, navigating points and miles becomes second nature.

The takeaway? Feeling frustrated doesn’t mean you’re failing—it’s a natural part of the learning curve!

Mistakes Are Part of the Process
Devon, Alex, and Jess share their own cringe-worthy redemption stories to remind listeners that no one starts as an expert. From redeeming points for DVDs on Amazon to cashing in for economy flights when premium options were available, everyone has made choices they’d change now. But as Devon points out, mistakes are how you learn—and each one gets you closer to becoming a points pro.

Practical Tips for Staying Motivated
Devon also offers practical advice for listeners feeling stuck. Her key tips:

• Focus on progress, not perfection.
• Use tools like Travel Freely and Seats.Aero to streamline the process.
• Set realistic goals based on your travel priorities.

And most importantly, don’t compare your journey to someone else’s. Whether you’re road-tripping with kids or planning a dream solo trip, success looks different for everyone.

Keep Going—You’re Doing Better Than You Think
If you’re feeling overwhelmed, tune in for a dose of encouragement and actionable steps to move forward. Devon’s insights will leave you inspired to keep learning, keep trying, and keep traveling.

Links:

• Links For All Things Travel Mom Squad: stan.store/travelmomsquad

• Where You Can Find Devon:
  • Website: https://pointmetofirstclass.com
  • Podcast: https://pointmetofirstclass.com/podcast
  • Instagram: https://www.instagram.com/pointmeto_firstclass

Episode Minute By Minute:

• 00:30 – Meet Devon and learn about her inspiring travel journey
• 07:00 – Breaking down the four phases of learning points and miles
• 16:00 – Personal stories: Mistakes, lessons, and growth
• 30:00 – Tools and strategies to simplify the learning process
• 42:00 – Final thoughts: Why you’re better at points than you think

It’s never too early to plan for your next adventure! In this episode, the Travel Mom Squad team looks ahead to 2025, sharing the trips we’ve already booked, the credit cards we’re eyeing, and our goals for the year. From Bora Bora to Spain, and everything in between, we’re setting the stage for another year of nearly free travel—powered by points and miles!

The Cards We’re Excited About for 2025
Jess kicks things off with a breakdown of the credit cards she’s targeting, starting with the Capital One Spark Cash Plus and a high-value 80,000-mile Alaska Airlines personal card offer. Pam and Alex are also planning to go for the Capital One Spark Cash Plus, while Alex shares how she’s strategizing with Citi AAdvantage business cards to maximize welcome offers. The key takeaway? Timing matters when it comes to opening new cards and meeting bonus requirements.

Trips We’ve Already Booked
Between the three of us, we’ve got a packed itinerary for 2025!

Highlights include:

• Jess: Birthday celebrations in San Miguel de Allende, spring break in Japan, and summer escapes to Iceland and Ireland.
• Alex: A Costa Rica adventure with her family, a Maui getaway, and a bucket-list trip to Bora Bora with her husband.
• Pam: A whirlwind journey through India, Nepal, and Bhutan, along with visits to Spain, Maui, and Bora Bora.

We talk about how planning trips far in advance ensures award availability and allows us to secure premium travel experiences.

Points and Miles Strategies for the Year Ahead
One thing is clear: flexibility is crucial for success in the points and miles world. Alex shares how she’s keeping her plans open for potential limited-time offers, while Jess talks about balancing her earn-and-burn strategy to maximize the value of her points. Pam reflects on how having a solid points balance gives her the freedom to take spontaneous trips or splurge on luxury experiences.

Make 2025 Your Best Travel Year Yet!
If you’re ready to make 2025 the year of nearly free travel, tune in to this episode for inspiration and actionable tips. We also share a free masterclass on how to get your next vacation for nearly free, so be sure to check the show notes for the link. Let’s make this your best travel year yet!

Links:

• Links For All Things Travel Mom Squad: stan.store/travelmomsquad

• How to Get Your Next Vacation for Nearly Free: https://travelmomsquad.lpages.co/freevacation

• How I Got Approved for the Capital One Spark Cash Plus: https://travelmomsquad.com/how-i-got-approved-for-the-capital-one-spark-cash-plus/

Episode Minute By Minute:

• 00:30 – Introduction: Looking ahead to 2025
• 01:00 – The credit cards we’re eyeing for 2025
• 11:00 – Our travel plans: Highlights from our booked trips
• 28:00 – Points strategies and staying flexible
• 31:00 – Points and miles goals for the year ahead
• 33:00 – How to make 2025 your best travel year yet