Episode #317: The Tuscany You Dreamed Of (and How to Find It)

This article may contain compensated links. See our full disclosure here

Listen to “317. The Tuscany You Dreamed Of (and How to Find It)” on Spreaker.

LISTEN ON APPLE LISTEN ON SPOTIFY DOWNLOAD TRANSCRIPT

Golden fields, hilltop towns, and unforgettable sunsets set the scene as we explore Tuscany’s quieter side, sharing evocative moments and insider stories that reveal the true soul of life in the Italian countryside.

Contents

Summary

Host Katy Clarke is, once again, joined by Olivia Windsor – Untold Italy Tour's Chief Experience Officer, to explore Tuscany in spring, from golden fields and rolling vineyards to storybook hilltop towns made famous on film. They share personal experiences beyond the tourist trail, including lively piazzas, family-run wineries, and hands-on rural encounters, revealing how to experience Tuscany in a more authentic and memorable way.

NEW FOR 2027: Our 10-day Tuscany Highlights Tour takes you from the rolling hills of Chianti to the Cypress Tree-lined valleys of the Val D'Orcia, with many untold treasures in between. Click here for more on the ultimate Tuscan adventure.

What you'll learn in this episode

Tuscany’s atmosphere is shaped as much by light, landscapes, and pace of life as by famous films, and why those cinematic images only hint at the deeper romance found in everyday village life
Katy and Olivia share what it feels like to experience Tuscany through the senses, from sunset light and piazza evenings to countryside walks, local sounds, and the smells of wood smoke, ragu, and pecorino
Authentic encounters matter more than polished attractions, including shared meals in vineyards, time with winemakers and farmers, and moments that connect travelers directly to the land and its traditions
Enjoy Tuscany’s iconic towns, wineries, and countryside without crowds by choosing the right seasons, seeking out local festivals, and favoring intimate, small-scale experiences over commercial ones
Practical insights into traveling in Tuscany, include when guided small-group tours, like Untold Italy's, add real value, how to balance independence with local expertise, and what to consider when driving and moving around the region

Timeline Overview

04:04 Tuscany’s romantic appeal is unpacked through its landscapes, atmosphere, and cultural pull, shaped by art, film, and everyday life rather than clichés
09:04 The role of light, sunsets, and the pace of life reveals why Tuscany feels so emotionally powerful, especially in small towns and countryside settings
14:02 What authentic travel in Tuscany looks like in practice, from moving beyond tourist experiences to forming genuine connections with people and place
20:43 How wine, olive oil, truffles, and farm-to-table experiences become meaningful when paired with personal stories from producers and time spent on working farms
32:08 Practical advice for navigating Tuscany, including why towns like Lucca feel more authentic, tips for driving, and how tours can simplify logistics while deepening experiences

About Untold Italy Tours

Untold Italy Tours creates small group journeys that take you beyond the guidebook and into the heart of local life. Each itinerary is carefully curated with our Italian friends to reveal authentic traditions, regional flavors, and the people who make Italy so unforgettable. Designed for curious travelers, our tours are intimate, effortless, and full of moments that feel like a dream come true.

Learn more: Untold Italy Tours website • Instagram • Facebook

About our guest – Olivia Windsor

Olivia, an Australian who moved to Italy in May 2019, and is based in Rome. She has recently launched the Italian wine site Italian Wine Tales with her husband Andrea, where you'll find not only the best wines to try, but also information on all the Italian wine regions, the best wine tours and wine clubs you can join.

Olivia has explored Italy from south to north, working in agriturismi and organic wineries before settling in Turin, Piedmont, for a few years after meeting a local Piemontese, Andrea. They are both now based in Rome and Olivia, Untold Italy's Chief Experience Officer, has created and hosted various Untold Italy Tours, as well as offering trip consults.

Follow Liv here

Italian places, foods and concepts mentioned

Places

Piazzale Michelangelo – piazza built on a hill outside of the historic center, with fantastic views back over the city
Antinori – wine producer with a winery you can visit to try a variety of wines, including Brunello
San Gimignano – famous Tuscan town popular with tourists
Lucca – charming hilltop town in Tuscany
Arezzo – this Tuscan town has a special Christmas, centered around Piazza Grande
Piazza dei Miracoli – formally known as the Piazza del Duomo, this is where you will find the Leaning Tower of Pisa

Words / Concepts

Under the Tuscan Sun – book by Francis Mayes, turned into a movie
A Room with a View – 1980s movie set in Florence and Tuscany, based on the EM Forster novel
Cena in vigna – dinner in a vineyard
Enoteca – a wine repository to try local wines

Plan your Italian adventures with Untold Italy

If you're enjoying the podcast and are excited about going to Italy but are overwhelmed by all the options, why not hire our Italy travel experts to help you build your dream trip. Our Italy Trip Planning services will get you from dreaming to booking the trip that suits you and your travel companions best – whether it's a week in Tuscany, visiting the iconic Italian cities or an off-the-beaten-path adventure in Sicily > learn more.

THE BEST!

If you want a curated Italian adventure, this is your solution. We hired Tyla and the Untold Italy crew to put together our itinerary through Tuscany. We had the vacation of a lifetime! – Jamey Ice (Google) – read more reviews.

Untold Italy Tours

Founded in 2022, our small group tour company takes curious travelers on multi-day adventures to Italy's lesser-known regions and to secret spots in places that are better known. Departing in Spring and Fall/Autumn, each trip focuses on food and wine, local traditions and uncovering the Italy you've always dreamed of > learn more.

NEED SOME HELP planning your Italy trip?

There is no shortage of Italy travel advice online. The problem is finding the right advice for your trip. Our Italy travel experts have helped hundreds of travelers go from overwhelmed to booked, with a plan they are excited about. Whether you have a loose idea or a half-built itinerary that needs a second opinion, we can help.

Talk to an Italy trip planning expert

Disclosure: Untold Italy assists our readers with carefully chosen product and services recommendations that help make travel easier and more fun. If you click through and make a purchase on many of these items we may earn a commission. All opinions are our own – please visit our disclosure page for more information.

Podcast episodes, Tuscany