In this week’s Midweek Mini, we’re breaking down one of the biggest and best deals in the entire world of points and miles — the Southwest Companion Pass. Whether you’re new to travel hacking or already a seasoned Southwest flyer, this episode walks you through exactly how to earn and maximize this incredible perk.

We share two main strategies to earn the pass — the classic two-card combo (personal plus business) and the real-life “no business card” approach — and explain how to time your spending perfectly so your pass lasts nearly two full years. You’ll also hear why this perk is so special for families and frequent travelers, along with a few important warnings about timing your spend before and after January 1.

We also dive into recent and upcoming Southwest changes, from assigned seating and new card perks to controversial snack and accessibility policy updates. Despite the changes, we both agree that if you fly Southwest even a few times a year, this is still one of the most valuable deals you can grab in travel.

If you’ve ever wondered how to earn 135,000 qualifying points the smart way, when to open your cards, or how to make your pass last the longest, this episode has everything you need to know. We’re sharing our own Companion Pass experiences, what worked, what didn’t, and why this deal continues to be one of our all-time favorites for families who love to fly for nearly free.

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This week on the Wonderland on Points podcast, we’re joined by Jenna from @TravelersinLaw for one of the most sporty trips we’ve ever talked about — her points-and-miles-fueled adventure to Milan for the Formula 1 Italian Grand Prix. We go behind the scenes on how it all happened, from locking in flights right when the availability opened to booking last minute puddle jumpers and hotels using points.

Jenna shares what it’s like attending an F1 race in Italy as a super fan. We talk about how she booked her flights and where she stayed, plus what the experience was actually like once she was there — the atmosphere, the food, the people, and the chaos that only Italy can deliver.

We also chat about how this trip fits into the bigger picture of the dreams that points and miles can make possible.

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This week, we begin with some less than thrilling news in the points and miles world. We love to keep you up to date but it's not always fun to share. THEN- we’re pulling back the curtain on how a trip actually comes together — from that first spark of inspiration to locking in the flights. It started with an Instagram video, a great transfer bonus, and some unbelievable business class redemptions, and by the end of the day, we had a surprise trip booked.

We walk through the entire process of figuring out where to go, how to get home, what the taxes and fees really looked like, and how we turned a spur-of-the-moment idea into a birthday trip of a lifetime.

If you’ve ever wanted to see what it looks like to build a trip with points in real time — the thought process, the strategy, and the excitement — this episode is for you.

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In this episode, we’re joined by Allison from @PointstoBoardingPass to break down one of the most powerful but underrated perks in the award travel world — Air Canada’s Aeroplan stopover program. Allison shares how travelers can add a stopover of up to 45 days for just 5,000 extra points and walks us through exactly how to find and book these deals using tools like Seats.aero and Air Canada’s multi-city search.

We talk about how to maximize this feature for business class OR economy redemptions, why it’s a great option for honeymooners or anyone wanting to hit multiple destinations on one trip, and how it can unlock extra award space on tough routes. The conversation also covers the pros and cons of Aeroplan’s family pooling, the hidden risks that come with it, and which airlines to avoid for smoother bookings.

Allison shares her own experiences using Aeroplan, including how she saved 30,000 points by adding a stopover, and what she’s planning next with points — from Scandinavia to the France. It’s a fun, practical deep dive full of tips, laughs, and strategies that will have you rethinking what’s possible with your points.

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Citi just launched a new American Airlines card - the Citi Advantage Globe Mastercard - and we are diving into what makes it stand out. With a $350 annual fee, it comes with solid perks like four Admiral’s Club passes, a domestic companion certificate, and Turo and Splurge credits that feel a little hit or miss. We break down the 90,000-mile welcome offer, easy $5,000 minimum spend, and new “Flight Streak Bonus” that helps earn AA status faster. Tune in as we share who this card actually makes sense for and whether it’s worth a spot in your wallet.

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In this episode, Jo shares the story of an unforgettable road trip — four teenagers, one mom, and a weekend that proved you don’t have to go far (or spend a fortune) to make magic happen. What started as a plan to see a concert turned into a full-blown adventure that got the teens off their devices and completely hooked on exploring a small town full of surprises.

From finding a Hyatt stay for just 6,500 points a night to discovering amazing free activities and local gems, Jo walks through how this spontaneous trip came together using points and miles. You’ll hear how she planned it, what made the destination so special, and why this road trip stands out as one of her favorite examples of affordable, meaningful travel with teens.

If you’ve ever wanted to plan an epic getaway that actually connects with your kids (or your kids’ friends) this episode is full of ideas and inspiration for using points and miles to create memories that last long after the trip ends.

Special thanks to Visit Bentonville for partnering with us on this incredible episode.

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In this midweek mini, we’re back from the TravelMore Conference and sharing all the behind-the-scenes details. From reconnecting with our favorite points-and-miles friends to some wild things we learned — and a few future guests who will be joining us on the podcast — we’re diving into everything that made this weekend truly amazing. We also get into “The Big Leak,” potentially the biggest points-and-miles news that could change the game forever. We break down what it means, why everyone’s talking about it, and what travelers like us should know going forward. If you’ve been curious about what TravelMore is really like or just want to catch up on the latest buzz in the points world, this quick episode is the perfect listen.

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This week on Wonderland on Points, we’re chatting with our friend Joy from @SavvyTravelMamas about her family’s European Harry Potter trip—and how she made it all happen with points. From planning the Warner Bros. Studio Tour in London to finding family-friendly stays, Joy shares the highs, the hiccups, and what she’d do differently next time. She talks us through the best tips and tricks for an amazing Harry Potter experience in both London and Scotland.

We talk through the logistics of using points for flights and hotels, balancing Harry Potter experiences with other sightseeing, and how to make big international trips feel manageable. Whether you’re a Potter fan or just dreaming of a magical European family adventure, this episode is packed with practical tips, honest reflections, and plenty of travel inspiration.

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