Today on the show, we’re joined by our friend and listener Holly to hear all about her incredible points and miles trip to San Diego! From staying at a hotel that would have cost nearly $11,000 for $0 out of pocket to using TWO Companion Passes for flights, this trip is a perfect example of just how far a good points strategy can take a family.

Holly breaks down the cards and strategies that made the trip possible, including how she used bank bonuses and Capital One miles to cover excursions and other vacation expenses. We also get into the details of where they stayed, what they did, and her honest reviews of the properties and excursions along the way. This was truly a mind-blowing vacation with next to nothing out of pocket!

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The news just keeps coming! This week, we’re breaking down the new Chase Freedom Flex Q4 bonus categories, including why dining and groceries could make this an especially lucrative quarter. We also talk about Qatar making it easier to book award flights for friends and family, a huge 70% Chase-to-Marriott transfer bonus, reported delays with some Amex transfers, and a pretty painful Wyndham devaluation.

Plus, Chase is celebrating the Sapphire Reserve’s 10th anniversary with new limited-time perks and credits. We go through what’s included, which ones we think are actually useful, and how we might take advantage of them. And finally, we clear up the difference between joining Wonderland Besties through Patreon versus subscribing through Apple Podcasts—and why we wanted to give you both options.

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This week, Jamie joins us to recap her family trip through Grand Teton and Yellowstone National Parks! She shares how they used Southwest points and a Companion Pass to fly into Boise and home from Bozeman, plus how they covered lodging with Wyndham points, Capital One miles, and credit card benefits. We talk about exploring Jenny Lake, Hidden Falls and String Lake in the Tetons before cold and rainy weather completely changed their plans.

Then it’s on to Yellowstone for bison, bears, Old Faithful, the Grand Canyon of Yellowstone, the Grizzly and Wolf Discovery Center, and some seriously wild traffic. Jamie also shares what she would do differently next time, where she would stay, and her biggest tips for planning a Yellowstone and Grand Teton trip with kids. This one is full of practical advice for planning your own national parks adventure—and a good reminder that sometimes the best family trips require a little flexibility!

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This week’s Midweek Mini has some important travel updates plus a BIG Wonderland on Points announcement! We’re talking about the new Trusted Traveler app replacing the old Global Entry app, Alaska Airlines making international lap infant award travel much more affordable, and the current Capital One Venture offer. We also cover a major change to Chase-to-Hyatt transfers and what you may want to do before it takes effect. Then, Wonderland Besties is officially HERE! We’re breaking down everything included in our new membership, from bonus episodes and ad-free listening to timely news, voicemail questions, community input, giveaways, group trip access, and more—plus we explain the differences between joining through Patreon and Apple Premium.

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Elizabeth von Tersch from U.S. News & World Report joins us to break down the latest rankings of the best airline and hotel loyalty programs—and there are definitely some surprises! We talk about why American took the top airline spot, what caused Atmos and United to fall, why JetBlue is gaining ground, and where Delta struggles. On the hotel side, we dig into Wyndham taking #1, why Hyatt remains strong despite its smaller footprint, and how programs like Choice, Hilton, Sonesta, and IHG compare. Plus, we talk about devaluations, transfer partners, redemption value, and why your points are almost always worth more today than they will be tomorrow.

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This week’s Midweek Mini is packed with good news! We’re talking about Southwest’s plans for new airport lounges and how a potential new premium Southwest card could impact Companion Pass strategy. We also break down the Chase Sapphire Reserve’s DoorDash restaurant credit increasing, Rove adding Copa Airlines as a transfer partner with a limited-time bonus, and some great Copa redemption sweet spots. Plus, we’re sharing a BIG Wonderland on Points update that you don't want to miss!

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We’re recapping Joanna’s incredible father-daughter trip to Alaska and breaking down how she made such an epic trip surprisingly budget-friendly! We talk about flying from St. Louis to Anchorage for just 17,500 points each way, using Hyatt points for the hotel, renting a car and exploring on our own, and deciding which experiences were actually worth the splurge. From trekking and rappelling on Matanuska Glacier to hiking in Girdwood, exploring Whittier, spotting beluga whales, picking wild blueberries in Hatcher Pass, cruising Kenai Fjords National Park, and finally finding a moose at sunset, this trip was packed with bucket-list moments. Joanna also shares why experiencing Alaska with her dad made this one of the most meaningful trips she’s ever taken—and why she came home already wanting to go back.

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This week, we’re catching up on a little bit of everything! We share an incredible VIP Minnesota Vikings experience made possible by one of our listeners, plus how we used points for the trip and checked out some unique Priority Pass options at MSP. We also talk about a recent credit card fraud scare, why we prefer credit over debit cards, and our strategies for earning the Southwest Companion Pass. Plus, we’re covering spring break planning, an important reminder to always register for Hyatt promos, and some new Rove features we’re excited about.

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Kirsten, a pediatric emergency medicine doctor and mom of three, joins us to break down how her family spent six nights in Puerto Rico for just $1,500 out of pocket on a trip that would have cost around $12,000 in cash. We get into exactly how she pulled it off using JetBlue points, Hyatt points, credit card travel credits, rental car status, and a Hyatt Guest of Honor award. Kirsten walks us through their stay at the Hyatt Regency Grand Reserve, why Guest of Honor benefits saved them hundreds of dollars on breakfast and parking, and how Puerto Rico turned out to be an incredibly easy family destination for a February school break. We also talk about their adventures in El Yunque, natural waterslides and cliff jumping in the rainforest, a canceled snorkeling excursion that led to a great backup day at Luquillo Beach, and exploring historic Old San Juan. Plus, we cover the Capital One offer that earned Kirsten an incredible 30X on a Viator excursion, her favorite points and travel tools, and why Puerto Rico deserves a spot on your list if you want beaches, adventure, history, and tropical weather without needing a passport.

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SURPRISE! For the first time ever, Wonderland on Points is dropping a brand-new episode on a FRIDAY. We just could’t wait on this one because Rove has massive new updates! We’re talking a NEW Rove app, Rove Dining, Instant-Earning Gift Cards and more!

We’re joined by Carissa Rawson from Rove to talk about the exciting new developments within the Rove program. If you’re already using Rove—or have been curious about how it could fit into your points-and-miles strategy, you’ll want to hear what’s coming next.

Carissa gives us an inside look at Rove, explains what makes the program different, and shares several new changes designed to make earning and using rewards even more exciting. We also discuss how travelers can take advantage of the program and why Rove is one to watch in the points-and-miles world.

Tune in for all the details—and enjoy this special Friday surprise!

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