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Point Me To First Class

Point Me To First Class

Written by: Devon Gimbel MD
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Point Me to First Class is a show for employed professionals, solopreneurs, entrepreneurs, and business owners with higher-than-average personal and/or business expenses who want to learn to leverage them into credit card points to spend on travel. Your expenses are your greatest untapped asset - but learning how to use them to travel the world doesn't have to be confusing or complicated. Each week, Devon Gimbel shares valuable tips, tools, and strategies to help you uplevel your skills earning and redeeming credit card points and shows you how to spend them on incredible travel experiences. Interested in learning more about working with Devon? Visit www.pointmetofirstclass.com to learn more. This podcast is for you if you find yourself asking questions like: How do I earn credit card points and use them for travel? How can I make my expenses benefit me? How can I earn as many credit card points for as little spending as possible? How to maximize value from credit card points. How to earn credit card points for travel. Turn credit card points into travel.© 2025 Devon Gimbel MD LLC All Rights Reserved Social Sciences Travel Writing & Commentary
Episodes
  • 176. Two Points Experts, Two Takes on Park Hyatt Cabo and Alila Mayakoba
    Jul 13 2026

    If you've been eyeing one of Hyatt's newer Mexico resorts and wondering whether it's actually worth your points, you're not alone.

    I'm joined this week by Michele from Fancy Travel Pointers, and the two of us have both separately stayed at Park Hyatt Los Cabos at Cabo del Sol and Alila Mayakoba within the last six months. Instead of each doing a solo review, we decided to sit down and compare notes, since we booked, stayed, and experienced both properties independently and didn't come away agreeing on everything.

    We walk through exactly how we each booked these stays in points, what room categories and upgrades we landed, and how the two resorts stack up on rooms, pools, dining, and service. I talk about the exceptional pool service and an unexpected ear-piercing emergency at Park Hyatt Cabo, and Michele shares why the lagoon side sold her on Alila Mayakoba over the beach. We also get into the dining misses at both properties, whether either one has a kids' club, and how Hyatt's newly changed award chart is reshaping whether a category 8 redemption like Park Hyatt Cabo still makes sense going forward. Michele also weighs in on how both properties compare to the neighboring Waldorf Astoria Los Cabos Pedregal, long considered the pinnacle points redemption in the area.

    Whether you've got one of these resorts on your wish list or you're just trying to figure out where your Hyatt points go furthest right now, this conversation should help you decide.

    Get full show notes and transcript: https://pointmetofirstclass.com/park-hyatt-cabo-vs-alila-mayakoba

    Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

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    1 hr and 12 mins
  • 175. Why Aeroplan Belongs in Every Traveler's Award Strategy
    Jul 6 2026

    Have you ever transferred miles into a program and then realized you only ever use it to book the same handful of flights everyone else does?

    Air Canada Aeroplan might be the most useful airline program that US travelers consistently overlook, and after this conversation I think you'll see why so many experienced points and miles enthusiasts treat it as a core part of their strategy. Today I'm talking with Anshul Singh of Points, Miles, and Bling, who has spent years inside the Aeroplan ecosystem and has used it to book everything from business class to Europe to trips most people never imagine points can unlock.

    Anshul and I get into why Aeroplan hits a rare balance between being easy to use and deep enough to reward the people who dig in, and why its network of close to 50 airline partners is where the real opportunity lives. Listen as we talk about the overlooked partner bookings most travelers walk right past, like Brussels Airlines business class out of Washington Dulles and Emirates and Air Mauritius routes you would never expect through a Star Alliance program, how Aeroplan's stopover rules let you build a single ticket that visits more than one place, and the Hotel Savers chart that points airline miles at high-end hotels like Six Senses and Fairmont.

    We also cover the smart way to think about buying Aeroplan points around a promotion, and my favorite part of the whole conversation, how the same program that flies you to Europe can take you to see polar bears in Churchill, the northern lights over the Canadian Arctic, and whale pods up and down both coasts. Whether you're brand new to Aeroplan or you've transferred miles into it before and never looked past the obvious flights, this episode will change how you see the whole program.

    Get full show notes and transcript: https://pointmetofirstclass.com/air-canada-aeroplan-strategy

    Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

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    1 hr and 9 mins
  • 174. United MileagePlus Upgrade Awards: How to Book Polaris for Less Cash and Miles
    Jun 29 2026

    If you've ever looked at United Polaris business class prices and thought they were completely out of reach, you're not alone. They can be outrageously expensive to book whether you're eyeing paying cash or points.

    But what if there was a third path - something between paying full cash for a premium ticket and redeeming a massive amount of miles outright? Miguel Rueda, from the Let's Get to the Points podcast, shares about a strategy within the United loyalty program that most travelers either don't know about or completely overlook. It's called a Mileage Plus Upgrade Award, and understanding how it works fundamentally changes what's possible when you're flexible with dates and routes.

    Miguel and I discuss what these awards actually are, how they differ from traditional award bookings, what PZ space means and why it matters for this strategy, and how to search for and confirm these upgrades. We walk through the specific mechanics of how this works, the tools you'll need, how to enable expert mode on United's platform, and the step-by-step booking process. We also explore when this strategy offers exceptional value and which routes and regions consistently show the strongest availability for premium cabin seats.

    Whether you have United miles, transferable points you can move into United, or just a willingness to mix a little cash with your miles, this episode reveals how multiple Polaris seats can be available on a single flight—a game-changer for families and groups that have struggled to find premium cabin availability elsewhere.

    Get full show notes and transcript: https://pointmetofirstclass.com/united-mileageplus-upgrade-awards

    Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

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    43 mins
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