Families Fly Free

Rachel says "I found my thing" when it comes to travel rewards and suggests "you can't go wrong investing in memories." Learn how this mother of grown kids has upgraded her travel rewards skills to take her family on a trip not "if" but "when" and "where" ever they want. She's even been able to fly to California for "lunch" and to take her daughter on a flight just to try on a wedding dress. What'...

Are you waiting to travel "someday" when you have more time or money? Portland realtor Bret Crawford shares how he went from barely earning enough Southwest points to flying free multiple times a year – and why the book Die with Zero convinced him to stop waiting. In his 60s, Bret's embracing the "go-go years," traveling as much as he can before he gets to the "slow-go" and then "no-go" years. Whe...

Think transferring Chase Sapphire points to Southwest will get you closer to Companion Pass? Think again. In this episode, I'm clearing up the biggest confusion around earning the Southwest Companion Pass—because the rules aren't what most people assume. I'll walk you through: The major mistakes people make (including that Chase transfer trap) Why "bonus points" don't always mean what you think Th...

The travel rewards landscape is shifting, and 2026 requires a new approach. In this episode, I'm walking you through 6 specific changes you need to make to keep flying your family for free—whether these are strategies you've clung to for years or adjustments necessitated by recent bank and airline policy changes. What you'll learn: Why constantly opening new cards needs to stop (especially with Ch...

Ever wonder if you can really cover an entire international vacation with points—not just flights, but hotels, vacation rentals and more? In this episode, I walk you through exactly how I took 3 of us to Costa Rica and saved more than $10,000 strategically using miles and points. Here's what you'll learn: How breaking Southwest flights into segments can save you thousands of points The incredible...

Did you accidentally earn your Southwest credit card bonus too early this year? You're not alone! Every year, people reach out who've made timing mistakes with their Companion Pass strategy—and it's happened more than usual in 2025 thanks to those amazing 100K+ credit card offers. In this episode, I break down exactly what went wrong, why timing matters so much at year-end, and most importantly—wh...

In this week's episode, I share with you all my best tips for maximizing the number of miles and points you can earn on your holiday shopping. You'll learn how to: Earn airline AND flexible points inside shopping portals How to earn points IN store How to stack points-earning How to get EXTRA discounts on top of earning points How to earn points at Amazon and Target Use all the points you earn for...

Forgetting travel credits, letting points expire, missing credit card bonuses—sound familiar? You're not alone. In this episode, I'm sharing 1 simple strategy to stop leaving money on the table and start maximizing every mile and perk you already have: simplify by conducting a card audit. I'll walk you through how to decide what cards to keep, to close and to set aside, so you can take a big sigh...

This week I’m chatting with Families Fly Free member Dave Banks —a dad of 4 from rural Oregon—who went from “credit cards are only for emergencies” to saving $2,367 on just 2 trips using my simple system. Dave shares how he and his wife flew to the Florida Keys for as low as 5,000 points each way with the Companion Pass, why the Families Fly Free Community has been the biggest surprise, and how th...

Staying successful with Southwest means keeping up with nonstop change — and that’s where I come in. In this episode I break down the latest boarding scoop from the Wall Street Journal and everything else they've announced in the last few months. I discuss the simple way to avoid paid seat headaches — lost seats on changes, messy expiring credits and poor points-plus-cash value — by booking in poi...

❓Got questions about how Families Fly Free can help your family travel to more places using miles and points BEFORE the price goes up soon ? In this episode, I share a replay of a recent 🧑‍🧑‍🧒‍🧒 Families Fly Free Open House with 4 current members on hand to answer attendees' questions honestly and directly. We had a HUGE turnout and so many great questions AND answers from our amazing members...

If I had to start from zero with travel rewards today, here’s exactly what I’d do — and what I’d skip.  Fresh off a Families Fly Free member meetup in California wine country 🍷, I’m sharing the simple, real-time strategy my Families Fly Free members use to keep flying free without juggling 20 cards or chasing outdated advice. You’ll learn why narrowing your focus is the fastest win: master flying...

Booking hotels through travel portals can be a brilliant points-saver, but there are also downsides to booking this way. In this episode I break down when portals like Chase Travel and Capital One beat transferring points to Marriott, Hilton or IHG, the risks of these bookings and the simple steps I teach my Families Fly Free members to mitigate any issues. We’ll also cover the powerful Hyatt exce...

Capital One Venture X is changing this popular perk that made it one of my favorite travel cards! Find out what's changing and WHEN and my strategy for what to do next... To stay on top of the lastest and ever-changing strategies in the world of travel rewards + learn my simple Fly Free Formula, join me inside of my hallmark Families Fly Free membership. Learn more at https://www.familiesflyfree.c...

Is this the end of travel rewards as we know it? 😱 Staying successful with miles and points in 2025 means keeping up with nonstop change — and that’s where I come in. In this episode I break down the biggest shifts I’m seeing right now from banks tightening approvals to pricey lounge access to Southwest’s new complexities — and offer 5 things you need to know as a result to keep flying free. I’ve...

Ready to add a little spooky fun to your travels this fall? 🎃 In this episode of the Families Fly Free podcast, I’m joined by Heather Alexander, author of Haunted USA , to uncover eerie—and family-friendly—ghost stories from all 50 states.  From haunted hotels and mysterious lighthouses to tap-dancing ghosts and legendary pirates, you’ll discover plenty of places to explore this Halloween season...

Southwest has made a flurry of changes in 2025 — from charging for bags and introducing assigned seats to rolling out brand-new fare types and tweaking credit card perks, including increasing their annual fees. And they’ve managed to make things very complicated. But here’s the good news: I’ve cut through the clutter to get to the heart of what actually matters in my trademark "keep it simple stup...

Ever stood in front of a famous painting and wondered, “What am I supposed to do here?” In this first episode of my new Wander in Wonder series, I dive into how to truly appreciate art — even if you don’t consider yourself an expert (I certainly don’t!). Inspired by a class I took at Notre Dame on Theology, Art and Beauty and my professor Dr. Sarah Maple ( https://sarahelizabethmaple.academia.edu/...

In Part 2 of my conversation with Chad Pennycuff ( My DVC Points Podcast ), we’re diving deeper into Universal Orlando’s brand-new theme park: Epic Universe — and there’s so much more to explore! After attending the Grand Opening event for media, I share my insight on the parks along with Chad's an Orlando local and "theme park junkie." This episode covers: 🍕 The best food in the park (hello, tru...

In this episode, I’m joined by Chad Pennycuff of the My DVC Points podcast to break down everything you need to know about Universal Orlando’s brand-new theme park, Epic Universe — starting with where to stay, what to skip and how to save. I share my experiences attending the Grand Opening event for media. We also recap Chad’s incredible theme park tour across Asia, including Shanghai Disney, Univ...

Join me for an insider’s journey to London as I share my favorite travel tips, hidden gems and even a few things I wish I’d done differently. In this episode, you’ll hear how I flew to London for (almost) free, where we stayed (and why it mattered), the must-see spots I recommend and how to get around the city stress-free — all from the perspective of a professional travel journalist. From Big Ben...

College visits, auditions, move-in weekends and campus drop-offs — they’re all part of the college journey… and they can get really expensive, really fast. But what if you didn’t have to stress about the cost? In this episode, I share how I recently visited Notre Dame using points and stayed right on campus without spending a dime — plus how Club members like Heather, Amylee and Yolanda have used...

Chase Sapphire Preferred is my FAVORITE Travel card — and right now, it’s offering a limited-time 100,000-point bonus (worth at least $1,250 in free travel) that ends May 15 at 9am ET . Thanks for using my personal affiliate link to support the podcast if you decide to apply for the card: https://www.familiesflyfree.com/favorite-card But beyond the big bonus, this card quietly packs in some powerf...

Southwest Airlines is shaking things up—starting with assigned seating in January 2026 and a new policy that could mean paying for checked bags . 😲 But don’t panic! In this episode, I’ll walk you through exactly what’s changing, what’s not changing, and most importantly—how you can still get your checked bag s free and snag a great seat without paying extra. We’ll cover: ✈️ How to navigate the ne...

Ever feel like travel is more stressful than it should be? You’re not alone — and you’re not imagining it. In this episode, I unpack the real reason travel feels overwhelming: No one ever taught us how to do it well. From not knowing if you passport will pass muster to panicking when a flight gets canceled, most of us are just guessing our way through trips — and that leads to stress, wasted money...