If you’ve ever thought award travel isn’t possible with a large family or group, this episode will change your mind.
In Part 1 of this conversation, I sit down with Dr. Alison Curfman, a pediatric emergency physician, entrepreneur, and relentless optimizer who regularly travels the world with her family—typically six to eight people depending on whether au pairs or grandparents join. After co-founding a healthcare company that scaled to a nine-figure valuation, Alison transitioned into advisory and consulting work that she could do from anywhere. Listen in as Alison walks through her exact strategy for finding business class flights for large groups, her hotel booking approach that keeps everyone comfortable without breaking the bank, and why positioning flights have become part of the adventure rather than a hassle.
We cover how she anchors her trip planning around long-haul flights, builds itineraries around award availability instead of fixed destinations, and uses spreadsheets and organization systems to keep track of multiple bookings across airlines and hotels. Allison also shares practical insights on traveling light with kids, leveraging Hyatt’s loyalty program strategically, and combining fine hotels & resorts credits with points to maximize value on family trips.
Whether you’re traveling with four people or eight, this episode offers a roadmap for making large family award travel not just possible, but truly enjoyable.
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Point Me to First Class is the show for professionals and business owners with higher-than-average personal or business expenses, who want to learn to leverage these expenses into credit card points they can spend on travel.
Each week, I share valuable tips, tools, and strategies to help you uplevel your skills earning and redeeming credit card points, so you can expand your travel and expand your experiences.