Episode #305: How to Tour Sicily - Beyond Sightseeing to the Heart of the Island

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Considering a trip to Sicily and wondering how to build the ultimate island itinerary? Filled with vibrant cities, dramatic landscapes, and unforgettable food, Sicily offers a wealth of experiences but can be challenging to navigate. Explore the island’s must-see highlights, authentic local experiences, and practical tips to help you plan a Sicily journey that feels rich, immersive, and truly your own.

Contents

Summary

In this episode, we welcome back Olivia Windsor, Chief Experience Officer and host of Untold Italy Tours, as we journey through the unforgettable island of Sicily, exploring its dramatic landscapes, layered history, and vibrant food culture shaped by centuries of influences and the ever-present force of Mount Etna. From lively city markets and ancient Greek temples to quiet countryside moments sharing homemade cannoli, this episode brings Sicily’s energy and warmth to life, with practical tips on when to go, how to get around, and why an Untold Italy small group tour can bring local insight that makes all the difference when creating a truly memorable Sicilian itinerary. In 2026, the Spring tour runs from 5th – 16th May and the Fall tour from 1st – 12th October. Discover the full itineraries and learn how to get in touch at untolditalytours.com.

LEARN MORE: About Untold Italy’s Sicily Spring and Fall tours here.

What you'll learn in this episode

Sicily feels so alive and different from the rest of Italy – from the constant presence of Mount Etna to the island’s vibrant street life, passionate people, and energy that many travelers describe as instantly emotional and unforgettable
Sicily’s layered history shapes everything you experience, with Greek, Roman, Arab, Norman, and French influences visible in its architecture, food, landscapes, and local traditions, creating a cultural richness unlike anywhere else in Italy
The kinds of “only in Sicily” experiences that define a visit – include volcanic wineries on Etna, bustling markets in Palermo and Catania, countryside cooking sessions making cannoli, and walking among ancient Greek temples in Agrigento
Personal connections with locals transform a Sicilian trip, from meeting family-run producers and artisans to sharing meals and stories that help visitors feel welcomed, understood, and deeply connected to the island’s culture
How to plan a Sicily itinerary that truly works, covering why the island’s size can be deceptive, when a car is essential, where flying in makes sense, the best seasons to visit, and how local guides or small-group travel can remove stress and unlock deeper experiences

Timeline Overview

06:56 – Learn how Sicily’s timeless traditions still shape daily life, from religious festivals and family rituals to the storytelling culture that keeps history alive across generations
09:58 – Discover why Sicily may look small on the map but feels vast in experience, with its layered history, diverse landscapes, and the emotional depth travelers encounter as they move across the island
12:59 – Understand the value of guided, immersive travel in Sicily, where local knowledge opens doors to deeper cultural connections, meaningful encounters, and places you would rarely find on your own
18:31 – Explore Sicily’s hidden stories, including lesser-known towns, personal histories, and traditions that reveal the island’s soul beyond famous landmarks
29:24 – Find out why driving is essential for truly experiencing Sicily, allowing access to rural areas, wineries, small villages, and unforgettable moments that public transport simply can’t reach

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

Ragusa – Baroque town in the Val di Noto area of Sicily
Messina – a harbor city in northeast Sicily, separated from mainland Calabria by the narrow Strait of Messina
Catania – Sicily’s second-largest city
Taormina – a town on the east coast that has been a tourist destination since the 19th century
Cefalù – seaside town you can visit easily from Palermo by train, bus or private transfer
Palermo – Sicily’s largest and capital city
Ortygia – a small island that is at the historical center of the city of Syracuse. The island is also known as the Città Vecchia (Old City
Agrigento – incredible ruins in Sicily, known as the Valley of Temples

Food / Drink

Cannoli – classic ricotta-filled pastries
Mount Etna wine – amazing wines made in vineyards based on the volcano, with its fertile volcanic soil
saffron – prized in Sicilian cooking, it was introduced by Arab rulers in the Middle Ages and woven into the island’s cuisine, trade, and traditions as a symbol of wealth

Words / Concepts

White Lotus – comedy-drama series set in a tropical resort – it follows the exploits of various guests and employees over the span of a week

Plan your Italian adventures with Untold Italy

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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.

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Podcast episodes, Sicily

Episode #305: How to Tour Sicily – Beyond Sightseeing to the Heart of the Island