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

2024 was a year to remember! In this episode, we’re sharing our best of 2024 awards, from unforgettable hotel stays and flights to top credit card offers that helped us turn big dreams into reality. If you’ve ever wondered what points and miles can do, this episode will inspire you to dive in and start planning your own adventures.

Pam’s Picks: Bougie Moments at the Grand Hotel Victoria and Park Hyatt Abu Dhabi
Pam shares her top hotel stays of the year, starting with a stay in Lake Como. This “lifestyle of the rich and famous” property left Pam feeling like royalty, even as she joked about rocking athleisure among designer outfits. Her other favorite? The Park Hyatt Abu Dhabi, where she enjoyed incredible January weather and a suite upgrade that made her feel like she was living in a dream.

Alex’s Favorite Stay: Greece with a Twist
Alex highlights her stay at Canaves Oia Suites in Santorini. The breathtaking views, private infinity pool, and authentic cave house design made it a “pinch me” experience. This trip reminded Alex why points and miles are so worth it—making unforgettable luxury accessible.

Jess’s Overwater Villa Moment in Bora Bora
Jess couldn’t top her Conrad Bora Bora stay this year, calling it a “pinch me” experience. From the overwater villa to stargazing on her private deck, Jess shared how she turned a $15,000 dream trip into a reality with Hilton points. Her takeaway? These moments are priceless, and points make them possible.

Top Flights of the Year
Pam’s favorite flight was on the luxurious Etihad Apartments, booked with Air Canada miles for just 65,000 points. Her first-class experience, complete with caviar service and a private suite, was a highlight of the year. Alex shared a special memory of flying business class on Singapore Airlines, while Jess raved about Turkish Airlines’ new A350 suite, complete with the best corn soup she’s ever had.

The Best Credit Card Offers of 2024
The team also reviewed their favorite credit card offers of the year. Pam scored big with the Chase Freedom Unlimited. Alex loved the Chase Ink Business Preferred’s 120,000-point bonus, and Jess highlighted the Capital One Spark Cash Plus, which earned her 260,000 miles.

Looking Ahead to 2025
As the episode wraps up, the team reflects on the incredible opportunities points and miles offered in 2024 and teases what’s to come in 2025. Whether you’re just getting started or already a pro, there are plenty of offers and strategies to help you plan your best year of travel yet.

Want to Learn More?
If you’re ready to start making memories like these, check out our free webinar, How to Get Your Next Vacation for Nearly Free. The link is in the show notes—don’t miss it!

Links:

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

Episode Minute By Minute:

• 02:00 – Favorite hotel stays: Pam, Alex, and Jess share their picks
• 10:00 – Best flights: From Etihad Apartments to Turkish Airlines suites
• 22:00 – Top destinations: Portugal, Japan, and more
• 30:00 – Best credit card offers and strategies for 2024
• 39:30 – Looking ahead: What we’re excited about in 2025
  

As 2024 comes to a close, the Travel Mom Squad is reflecting on an incredible year of points and miles. In this special episode, we’re breaking down the credit cards we opened and closed, the strategies we used to rack up points, and the unforgettable trips we took along the way. If you’re curious how points and miles can transform your travel, this episode is a must-listen!

The Cards That Made 2024 Happen
Jess, Alex, and Pam each opened (and closed) a variety of cards to maximize their points strategies. From Chase Ink cards to the Hilton Honors American Express Surpass® Card, the team shares how they targeted cards with elevated welcome offers and leveraged creative strategies to earn millions of points.

Lessons Learned From Closing and Downgrading Cards
A major part of managing a points portfolio is knowing when to say goodbye. The team discusses their approach to closing and downgrading cards, emphasizing the importance of timing to avoid red flags.

A Year of Incredible Travel
From Bora Bora to the Italian Dolomites, 2024 was packed with bucket-list trips. Jess’s travel highlights included following Taylor Swift across the globe, visiting Tokyo, Scotland, and Santorini. Alex took her family on a trip to Amsterdam and London, and Pam reflected on her most cherished moments, from flying Etihad Apartments to enjoying three-generational family getaways. The best part? Nearly all of these adventures were made possible by points and miles.

The Emotional Impact of Points and Miles
Pam ends the episode on a heartfelt note, sharing how compiling her 2024 recap brought her to tears of gratitude. “This is something I never would have been able to do without credit card points and miles,” she says. The team agrees: this hobby is about so much more than just saving money. It’s about creating memories and opportunities that wouldn’t otherwise be possible.

Looking Ahead to 2025
The Travel Mom Squad is already planning for another year of unforgettable travel, and this episode is full of inspiration for how you can start planning your own points-powered adventures. Whether you’re a seasoned pro or just starting out, the lessons and stories shared here will motivate you to dream bigger and travel smarter.

Links:

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

• How I Got Approved for the Capital One Spark Cash Plus
• How to Get Your Next Vacation for Nearly Free

Episode Minute By Minute:

• 00:30 – Reflecting on an amazing year of points and miles
• 01:15 – Cards opened in 2024 and how they shaped our strategies
• 15:00 – Closing and downgrading cards: Tips and lessons learned
• 25:00 – Highlights from Jess, Alex, and Pam’s 2024 trips
• 35:00 – The emotional impact of creating memories with points and miles
• 38:00 – What’s ahead for 2025 - what’s coming up next on the show!

Ever wonder what kind of points and miles traveler you are? In this episode, the Travel Mom Squad dives into the different types of travelers and how your personal travel style can shape your points strategy. From planners to luxury travelers to earn-and-burn enthusiasts, we break down the styles that work best for different lifestyles and goals—and share what type of travelers we are, too!

Alex: The Planner and Strategist
Alex kicks things off by sharing how her style has evolved. As a planner, Alex focuses on specific trips she wants to take and chooses credit cards to make those trips happen. She balances planning with flexibility, chasing transferable points and limited-time offers that align with her travel goals. Her advice? Always keep the 5/24 rule in mind and prioritize cards that fit your long-term plans.

Pam: The Type-A Luxury Traveler
Pam describes herself as a “no-chill, Type-A overachiever” who loves the finer things in life. With over 5 million points and miles, Pam can book anything at a moment’s notice. Her strategy focuses on luxury—think first-class flights and five-star hotels. For those in a similar stage of life, Pam emphasizes making points work for you while enjoying the rewards of your hard-earned travel perks.

Jess: The Earn-and-Burn Expert
Jess takes a completely different approach: earning points quickly and redeeming them just as fast. “By the end of this year, I’ll have redeemed over a million Hyatt points,” she says. Jess avoids stockpiling points, knowing they devalue over time. Her philosophy? Use them while they’re at their peak value to create unforgettable family memories.

Other Traveler Types and Strategies

• The Domestic Traveler: Focused on U.S. destinations, this traveler maximizes Chase Ultimate Rewards and co-branded hotel cards for family road trips or visiting relatives.
• The Road Tripper: Ideal for families who avoid flying, this strategy uses hotel cards like Hyatt or Marriott to save on stays during sports tournaments or weekend getaways.
• The Disney Fanatic: For those who visit Disneyland or Disney World annually, Capital One cards help erase ticket purchases and make magical trips more affordable.

Your Travel Style, Your Strategy
There’s no “right” way to approach points and miles. The best strategy is the one that fits your lifestyle and goals. As Pam puts it, “You do you!”

Ready to Find Your Traveler Type?
Tune in to the full episode to hear more about each style and figure out which one resonates with you. Whether you’re just starting out or a seasoned pro, this episode will help you refine your strategy and make the most of your points.

Links:

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

Episode Minute By Minute:

• 00:30 – Introduction: How your travel style shapes your points strategy
• 01:15 – Alex: The planner and how she prioritizes flexibility
• 10:08 – Pam: The luxury traveler with 5 million points
• 15:23 – Jess: The earn-and-burn approach to points
• 21:30 – Domestic travelers, road trippers, and other styles
• 27:55 – Takeaways: Why any strategy can work for your goals

You’ve heard us share our travel stories and tips, but today we’re introducing you to three incredible women who help make Travel Mom Squad possible. Megan, Traci, and Claire aren’t just our teammates—they’re passionate travelers and moms with their own inspiring journeys in the world of points and miles. In this episode, we dive into how they got started, their favorite travel wins, and what keeps them motivated to help families travel better. Hit play to hear their stories!

Megan: From Student to Digital Manager
Megan is the glue that holds our team together, managing everything from card consultations to staying on top of the best credit card offers. A longtime points and miles enthusiast, Megan took her first points-funded trip to China in 2014, booking round-trip flights and two weeks of hotels for free! Fast forward to today, and she’s orchestrating epic family adventures, including a two-week trip to Hawaii and Australia. Her advice? Don’t be afraid to expand your plans. As Megan says, “We were already halfway to Australia, so why not go all the way?”

Traci: The Fact-Checking Pro
Traci’s role is all about keeping our blog and content accurate and compliant, but her travel experience is just as impressive. She’s been in the points and miles game for over a decade and even introduced Jess to this world! Traci shared highlights from her family’s DIY around-the-world trip, pieced together with points and miles. From art tours in Milan to a luxury cruise in Ha Long Bay, Traci’s travel philosophy is all about maximizing memories while balancing practicality. And yes, she admits economy ankles are real—but so is the joy of exploring new destinations!

Claire: Building Memories with Birthday Trips
As our Facebook community manager, Claire is a familiar face to anyone in our group. But did you know she started her points journey by buying Travel Mom Squad’s course for herself? Since then, Claire has turned family birthdays into opportunities for travel. Her next adventure? Taking her oldest to London and Paris for senior photos—a dream trip made possible with points.

The Takeaway: Your Team, Your Inspiration
What makes Travel Mom Squad special isn’t just the places we’ve been—it’s the team behind the scenes, working to help you unlock the magic of points and miles.

Whether you’re new to points or a seasoned pro, this episode will inspire you to dream big, plan smart, and keep making memories with your family. Tune in now to hear their stories and start thinking about your next adventure!

Links:

• Join Our FREE Webinar, Learn How To Travel Nearly Free! https://travelmomsquad.lpages.co/freevacation

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

Episode Minute By Minute:

• 01:15 – Megan’s role at TMS and how she got started with points and miles
• 07:00 – Megan’s most memorable family trip and how points made it possible
• 15:30 – Traci’s background in points and miles and her favorite travel style
• 22:45 – Traci’s incredible DIY around-the-world trip with her family
• 33:00 – Claire’s introduction: How she discovered TMS and her role as the Facebook community manager
• 41:00 – Claire’s approach to birthday trips and favorite points-based travel moments

Tired of long lines at immigration or security when traveling? We’ve got you covered! In this episode, the Travel Mom Squad revisits a favorite topic—Global Entry and TSA PreCheck®—but with a twist. While we’ve covered these programs before, there are important updates you need to know to make family travel even smoother. Whether you’re flying internationally or just looking to breeze through airport security, these tips are a game-changer.

New Updates You Can’t Miss
Since our last discussion on this topic, a major update now allows kids under 18 to get Global Entry for free if their parent or guardian is enrolled. Jess highlights how this policy change can save families hundreds of dollars—especially for large families like Alex’s. And if you’ve ever been frustrated by long wait times for Global Entry interviews, Alex shares how her family took advantage of the new interview-on-arrival option, skipping the months-long backlog to get everyone approved quickly. Jess also mentions that some airports, like San Francisco, are testing departure-day interviews, which could make the process even easier.

How to Get It for Free Using Credit Cards
Alex dives into the details of credit cards that reimburse Global Entry and TSA PreCheck® application fees. Popular options like the Chase Sapphire Reserve, Capital One Venture, and Amex Platinum cards make it easy to offset the costs. One pro tip: You can use the benefit on someone else’s application by paying with your card, so you can help friends and family members enroll too. Between these credits and the new kids-under-18 policy, Global Entry has never been more accessible.

Backup Options for Occasional Travelers
If you’re not ready to commit to Global Entry, Pam suggests Mobile Passport as an alternative. This app offers a shorter immigration line without the application process or fees. While it’s not as fast as Global Entry, it’s a great backup for infrequent international travelers.

The Key to Stress-Free Family Travel
Between Global Entry, TSA PreCheck®, and Mobile Passport, there’s no reason to deal with long lines at the airport. As Jess says, “Travel days are stressful enough—why not make them as easy as possible?”

If you’ve been putting off enrolling in these programs, this episode is your sign to get started. Tune in now to hear all the details and updates that will make your next family trip a breeze!

Links:

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

Links For This Episode:

• Mobile Passport Blog Post: https://travelmomsquad.com/no-global-entry-try-mobile-passport/
• Mobile Passport App: ‎Mobile Passport Control

Episode Minute By Minute:

• 00:30 – Revisiting Global Entry and TSA PreCheck® with important updates
• 07:00 – TSA PreCheck® benefits and why it’s worth it
• 10:30 – The best credit cards for free enrollment
• 15:00 – How the new kids-under-18 policy can save families money
• 20:00 – Alex’s tips for interview-on-arrival success
• 28:00 – Mobile Passport: A simple alternative for occasional travelers
• 30:00 – Final thoughts and why it’s time to enroll