Episode #318: Italy in Winter - Milan, the Olympics, and Getting Unstuck

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Planning a trip to Italy but finding yourself getting stuck with the logistics? Sometimes going beyond online research can help create a truly memorable Italian adventure to suit your specific needs. Discover the limits of DIY and AI-powered planning, and why local knowledge, thoughtful guidance, and a flexible approach can transform your trip into something far more meaningful and uniquely yours.

Contents

Summary

In this episode, host Katy Clarke welcomes Alex Tyron – technologist, startup founder, and passionate traveler – to share her family’s adventure at the Milan Winter Olympics and an Alpine ski trip. Joining from New York City, Alex reflects on how her love for Italy began in her teens and grew through art, culture, and travel. We explore the realities of planning an Olympic-time visit with kids, from navigating Milan’s accommodation challenges to discovering family-friendly ski resorts in the Aosta Valley. Alex also shares why local expertise still matters, the limits of online and AI trip planning, and tips for blending smart planning with the spontaneity of Italian travel.

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What you'll learn in this episode

Alex shares how she worked through common Italy trip-planning roadblocks – explaining why online research and AI tools often fall short, and how expert, on-the-ground advice helped her save time, reduce stress, and make better decisions
Alex structured her family’s Italy itinerary using key “trip anchors” to shape the journey, balance logistics, and create a realistic plan that worked smoothly while traveling with young children
She shares her firsthand impressions of Milan – including what surprised her most about the city, where she stayed, how she approached major attractions, and why it worked better for families than she expected
Thanks to her Untold Italy trip consultation with Tyla, Alex discovered a lesser-known ski destination in the Aosta Valley – and found choosing a smaller resort led to a more relaxed, authentic, and enjoyable experience for her whole family
Her takeaway from planning and traveling in Italy is that combining technology with local expertise, staying flexible, and embracing spontaneity ultimately created a far richer and more meaningful trip

Timeline Overview

04:08 Planning travel with AI tools – the benefits and limitations of using AI for trip planning, and why it often lacks the nuance and up-to-date detail needed for Italy
16:48 Rediscovering Milan’s charm – how the city surprised with its walkability, atmosphere, and family-friendly appeal, especially when staying in a local neighborhood
30:44 Discovering Aosta and Pila – choosing a lesser-known Alpine destination and what makes it a more relaxed, authentic alternative to major ski resorts
40:53 Letting go of overplanning – learning to adapt when things don’t go to plan, from booking challenges to on-the-ground hiccups, and embracing a more flexible approach
51:48 The impact of AI on expertise – why human knowledge, curated advice, and even travel agents are becoming more valuable in an increasingly AI-driven planning landscape

DISCOVER: Untold Italy's Personal Travel Assistant Zia, which Dewey founder Alex worked with Katy to create. Get answers to your questions using Untold Italy's expertise and information.

About our guest – Alex Tryon from Dewey Labs

Alex is a serial entrepreneur, angel investor, and enthusiastic eater. She is the co-founder of Dewey Labs, which builds custom answer engines that make expert knowledge accessible, without the hallucinations or internet average answers that make most AI search untrustworthy.

Previously, she co-founded Artsicle – dubbed “The Gallerists to the People” by The New York Times – and held senior roles at The Muse and Teachers Pay Teachers. She is a NYC Venture Fellow, a recognized Female Founder to Know, and an active advisor and mentor in the New York startup community.

Follow Alex here

Italian places, foods and concepts mentioned

Places

Milan – dynamic urban center in northern Italy; global capital of fashion and design, and also the host city for Olympic ice events
Cortina d'Ampezzo – glamorous Alpine ski town, known for luxury resorts and hosting Olympic skiing and curling events
Castello Sforzesco – historic castle in the center of Milan, surrounded by green space and public courtyards
Duomo di Milano – Milan’s awe-inspiring Gothic cathedral, a vital city landmark with panoramic rooftop views
Leonardo da Vinci Museum – interactive museum in Milan dedicated to da Vinci’s scientific and artistic achievements; popular with families
The Last Supper – Leonardo da Vinci’s iconic painting, whose viewing requires advance booking in Milan
Pila – small ski village above Aosta, noted for its family-friendly slopes, Italian mountain vibe, and immersive local experience
Aosta Valley – mountainous region in northwestern Italy, popular for skiing, hiking, and Alpine villages
Alps – extensive European mountain range, offering world-class skiing and breathtaking landscapes
Aosta – ancient Roman town in the Aosta Valley, serves as a gateway to nearby Alpine ski areas
Matterhorn – iconic Alpine mountain straddling Italy and Switzerland, renowned for skiing and mountaineering
Dolomites – UNESCO-listed mountain range in northeastern Italy, famous for stunning peaks, both winter and summer outdoor activities

Words / Concepts

Dewey Labs – company founded and run by Alex, specializing in AI-powered answer engines built on expertise from humans and organizations. Zia is Untold Italy’s custom-built online tool for Italian travel information, powered by Dewey Labs technology
Milan-Cortina 2026 Winter Olympics – international sporting event and the anchor of Alex’s family trip, as Alex's cousin was part of the Canadian women's hockey team
Salone Mobile Milano – the world’s largest and most prestigious furniture and interior design trade fair, held annually in Milan
Tyla – Untold Italy team member, expert on Milan and skiing, who helped Alex plan her family’s ski adventure
ChatGPT, Claude, Google – examples of generic AI platforms used for information search and planning
RAG system – ‘retrieval augmented generation’, a type of AI tool designed to answer questions based on specific, curated data rather than the wide open internet
Reddit – online community forum cited as one of the less reliable sources in AI’s “parametric knowledge”
Parametric knowledge – information AI bots have, derived from general internet sources and books, sometimes inaccurate or out of date

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Experiences, Podcast episodes

Episode #318: Italy in Winter – Milan, the Olympics, and Getting Unstuck