In this episode, we’re spotlighting a hidden gem in the MidEAST—Hocking Hills, Ohio. This is our SECOND submission from listener Katie shares all her top tips for visiting this stunning spot, from the best places to stay to must-do hikes and creative ways to book it all using points and miles.

We cover everything from rustic-chic state park lodges (bookable through Chase or Capital One) to romantic cabins with hot tubs and even luxury treehouses. Katie has visited in every season and swears you can’t go wrong, though fall is especially beautiful—just be sure to book early.

Whether you’re hiking through Ash Cave, sipping wine at a local vineyard, or cozying up by a fire in a cabin, Hocking Hills offers the perfect mix of relaxation and adventure. This is a road trip you’ll want to add to your list—especially if you’re looking for a peaceful escape that won’t break the bank.

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In this episode, we’re diving into one of the most aspirational redemptions in the world of points and miles—Alila Ventana Big Sur, a luxurious adults-only, all-inclusive Hyatt resort tucked along California’s stunning coastline. We’re joined by social worker and points enthusiast Deb, who shares how she booked this $1700+-per-night property using points, and why she says it was 100% worth it.

Deb opens up about how travel has become a vital outlet for avoiding burnout in her emotionally demanding career, and how discovering points and miles through a Chase Sapphire Preferred bonus changed everything. She walks us through her strategy for locking in a three-night stay at Ventana using Hyatt points, including how she searched for elusive award space using hotel search aggregator tools. She also shares details about getting there with airline miles, her room upgrade to a Big Sur suite, and all the stunning extras that made the trip unforgettable—like forest bathing, coastal hikes, beekeeping, and nightly s’mores.

If you’ve ever dreamed of staying at Ventana—or wondered whether luxury travel on a budget is really possible—this episode will inspire you to dream bigger and dive deeper into the world of points and miles. Deb also gives us a preview of her upcoming session at the Travel More Conference, where she’ll be teaching others how to find award availability for high-end hotels using advanced search tools.

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The above link includes referrals for Capital One Travel Cards. If you need AMEX or Chase please reach out and we would be happy to send you our personal referral links.

We receive a small commission when you use our links. This is an amazing way to show your support for the show at no cost to you ❤️

Today on our Midweek Mini we are taking a small break from summer road trips and we’re diving into the ever-evolving world of points and miles—and how we’re adjusting our strategy to keep up. With recent changes to Chase’s sign-up bonus language, we’re starting to shift our focus away from chasing (pun intended) welcome offers and instead doubling down on everyday spending and earning categories.

We talk about how the Chase Freedom Flex has become a staple in our wallets, especially when we can line up our real-life spending with the rotating categories. This quarter, Instacart and gas are big wins, and we break down how we’re using those to rack up serious points. We also share how tools like Card Pointers help us stay organized and make sure we’re always using the best card for every purchase.

If you’ve ever felt like the points and miles landscape is changing faster than you can keep up, you’re not alone. We’re in it with you—and in this episode, we walk through the exact strategies we’re using to keep earning more and spending less. Because even without a big sign-up bonus, there are still plenty of ways to keep your travel dreams alive.

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The above link includes referrals for Capital One Travel Cards. If you need AMEX or Chase please reach out and we would be happy to send you our personal referral links.

We receive a small commission when you use our links. This is an amazing way to show your support for the show at no cost to you ❤️

Today on Wonderland on Points, we’re heading out of the city and into the storybook charm of the English countryside! Jo shares all the highlights from her family’s recent road trip through two of England’s most picturesque regions: the Cotswolds and the Yorkshire Dales (with a fun little national park detour in between). From booking flights with points to tackling the adventure of renting a car and driving on the “wrong” side of the road, she walks through exactly how they made this dream trip happen—without blowing the budget.

You’ll hear about the magic of the Cotswolds, where each village felt like stepping into a Jane Austen novel, and the peaceful charm of Tewkesbury, including a visit to the breathtaking Tewkesbury Abbey. Joanna also talks about exploring the Yorkshire Dales on horseback, a highlight that brought a whole new perspective to the stunning scenery. Traveling by car gave their family the flexibility to chase spontaneous detours and discover unexpected gems along the way.

Whether you’re dreaming of a countryside getaway or already planning your own English road trip, this episode is packed with practical tips and inspiration for seeing the UK beyond the big cities—creating family memories that will last a lifetime.

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The above link includes referrals for Capital One Travel Cards. If you need AMEX or Chase please reach out and we would be happy to send you our personal referral links.

We receive a small commission when you use our links. This is an amazing way to show your support for the show at no cost to you ❤️

Today on another Midweek Mini—road trip edition—we’re bringing you a total gem for our Midwest listeners! Bentonville, Arkansas might not have been on your radar before, but it definitely will be after this episode. This small town is packed with surprises: world-class art at Crystal Bridges, a walkable downtown filled with charming shops and restaurants, incredible bike trails, and some seriously impressive food. Whether you're a history buff, foodie, art lover, or just need a peaceful weekend away, Bentonville truly has something for everyone. We walk you through where to stay, what to eat, and all the best things to do to make the most of your visit to this historic and unexpectedly cool destination.

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Today on Wonderland on Points, we’ve got BIG NEWS!

Chase just launched a brand-new welcome bonus for the Sapphire Reserve as well as ENTIRELY refreshing the earning and benefits and we’re breaking it all down in this episode. We’re joined by our go-to credit card correspondent, travel and finance journalist Katherine Fan, who helps us unpack all the details.

We’ll walk you through the updated annual fee, the refreshed bonus categories, and the current lineup of card benefits to help you decide whether the new Sapphire Reserve deserves a spot in your wallet. AND we will announce the BRAND NEW SHINY welcome offer.

After you listen, we’d love to hear your thoughts! Are you planning to apply for this revamped card, or is it a pass for you? Come join the conversation in our Wonderland on Points Facebook group and let us know!

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Our personal links may not YET reflect the elevated sign up bonus- but they will shortly! Thank you for choosing to use our links! These links can be used for ANY of the Sapphire cards.

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The above link includes referrals for almost all travel cards (AMEX, CapitalOne, co-branded cards)

If you need Chase links please reach out! We would be happy to send you our personal referral links or the Daily Drop newsletter link that will allow you to access our affiliate links.

We receive a small commission when you use our links. This is an amazing way to show your support for the show at no cost to you ❤️

In this Midweek Mini, we take you to the cobblestone streets and Spanish moss of Savannah, Georgia—submitted by Wendy. It is an amazing spot for a charming, walkable weekend escape. We chat about the best times to visit (spring and fall are ideal!), where to stay for easy access to the city’s highlights, and the can’t-miss food and experiences that make Savannah so memorable.

We share our love for the historic district and accommodations like the Andaz, which even includes bike rentals to help you explore. From iconic Southern dining at The Grey and The Old Pink House to strolling through Forsyth Park or along the river walk, Savannah offers something for everyone. We also touch on the city’s vibrant culture, including its lively nightlife and, of course, the wildly entertaining Savannah Bananas baseball team.

Whether you’re into history, food, or just soaking in the charm of the South, Savannah is a weekend destination worth adding to your list.

Submit Your Summer Road Trip Series Story HERE

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The above link includes referrals for almost all travel cards (AMEX, CapitalOne, co-branded cards)

If you need Chase links please reach out! We would be happy to send you our personal referral links or the Daily Drop newsletter link that will allow you to access our affiliate links.

We receive a small commission when you use our links. This is an amazing way to show your support for the show at no cost to you ❤️

In this episode, we’re joined by financial educator and profit strategist Jamie Trull for a conversation that bridges travel, family, and finance. Jamie shares how her background as a CPA led her to help families and small business owners make smarter financial decisions—and how those choices can open the door to more meaningful (and affordable) travel.

We dig into how points and miles fit into a bigger financial strategy, the importance of separating personal and business expenses, and when it might make sense to form an LLC or S-Corp. Jamie also breaks down the often-overlooked tax implications of credit card rewards and offers tips for keeping finances organized to maximize benefits.

One highlight? Our chat about teaching kids financial literacy—whether by adding them as authorized users, paying them through a family business, or simply involving them in travel budgeting. Jamie encourages families to create “fun funds” by setting aside a percentage of profits, making room for joy and connection without financial guilt.

This episode is packed with practical advice and empowering insights for anyone looking to make their money—and their miles—go further.

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Jamie's Resources

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The above link includes referrals for almost all travel cards (AMEX, CapitalOne, co-branded cards)

If you need Chase links please reach out! We would be happy to send you our personal referral links or the Daily Drop newsletter link that will allow you to access our affiliate links.

We receive a small commission when you use our links. This is an amazing way to show your support for the show at no cost to you ❤️