Episode #297: How to Travel Italy Your Way

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Are you torn between planning your own Italian adventure or joining a guided tour? The expert Untold Italy team breaks down the pros and cons of independent travel versus small group tours, sharing insider tips and real experiences to help you craft your perfect Italian journey!

Contents

Summary

Whether you’re planning an independent trip or joining a guided tour (or a mix!), this episode explores the pros and cons of each travel style – from flexibility and logistics to authentic local experiences. Our team of Trip Consultants, Tour creators and hosts – Olivia, Sarah, Guilia and Cassie – share how the Untold Italy Tours and their Trip Consultations help travelers craft personalized adventures, filled with meaningful connections, great food, and unforgettable memories across Italy.

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What you'll learn in this episode

Traveling independently offers flexibility, control, and the ability to create routines that suit your personal preferences, while guided tours provide a stress-free experience with access to local expertise, perfected itineraries, and unique venues that are often unavailable to solo travelers. Guests on small group tours also benefit from social sharing of meals and immersive cultural interactions, allowing them to experience Italy more deeply than they might on their own
The Untold Italy Small Group Tours, typically limited to around 12 guests, provide the ability to adapt itineraries to individual interests and add spontaneous experiences based on group dynamics. This flexibility allows travelers to visit off-the-beaten-path locations, interact authentically with locals, and engage in activities tailored to their passions, creating a highly personalized and memorable trip
Untold Italy’s planning and consultation services help travelers navigate logistics such as trains, driving routes, and connections, while offering tailored recommendations based on personal interests rather than generic popular sights. These services are particularly valuable for families, first-time visitors, or those with limited time, ensuring that every aspect of a trip – from must-see landmarks to hidden local gems – is optimized for a meaningful experience
Traveling in Italy can present practical challenges, from differing transport infrastructure compared with the US or Australia to unreliable online schedules in rural areas. Local guidance is crucial for overcoming these hurdles, allowing travelers to move efficiently between destinations and focus on enjoying the cultural, culinary, and historical richness of each region without unnecessary stress or delays
Experiencing Italy fully involves balancing iconic landmarks with authentic local experiences, such as sampling regional wines, exploring small towns, and connecting with local artisans. Guests learn to immerse themselves in the country’s diversity – from city to countryside to coast – while embracing opportunities for cultural discovery, personal growth, and meaningful connections facilitated by a knowledgeable and passionate travel team

DISCOVER: Untold Italy's Small Group Tours to Piedmont, Emilia-Romagna, Puglia, Liguria, Sicily, Tuscany, Umbria, the Dolomites and the new 12-day Northern Italy Tour.

Timeline Overview

07:03 Living Like a Local in Italy: Insights on immersing yourself in authentic Italian culture beyond typical tourist experiences
16:06 Benefits of Small Group Tours: How smaller, personalized tours enhance the travel experience and allow more meaningful interactions
26:11 Italy Travel Planning Made Personal: Tailoring travel plans to individual preferences for a stress-free, customized journey
33:34 Transport Schedules: US vs Italy: Comparing logistical differences in travel and transportation between the US and Italy
45:47 Experiencing Italy's Unique Charm: Exploring Italy’s distinct cultural, historical, and regional highlights for a memorable visit

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

About our guest – Giulia Tamarri

Giulia Tamarri from Travel with Rezdora is a qualified Tour Manager, Food Guide, and Untold Italy host from Castelfranco, between Modena and Bologna. After earning a degree in Foreign Languages from the University of Bologna, she spent nearly a decade abroad in Australia, New Zealand, and London, working in education and events before returning home to Emilia Romagna.

Now based in Spilamberto, the home of Traditional Balsamic Vinegar, Giulia has led more than 40 tours across Italy and Europe and trained as a certified food and wine expert for her region. Inspired by the “rezdora” – the skilled home cook who manages the family kitchen – Giulia brings the same passion, precision, and warmth to curating unforgettable culinary and cultural experiences in her beloved Emilia Romagna as well as hosting Untold Italy tours across Italy.

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About our guest – Sarah Marano

English-born Sarah and her Italian husband Salvatore created La Cuccagna in Umbria after meeting while paragliding and discovering a shared love of adventure and sustainable living. Together, they’ve turned their hillside farmhouse into a welcoming and luxe guest retreat where visitors can experience authentic Umbrian life surrounded by nature.

Sarah is deeply committed to sustainability – reusing original materials in the property’s restoration, using solar energy and olive-nut fuel for heating, and sourcing furnishings, produce, and handmade ceramics from local artisans. Much of the food served comes from their own organic farm, where they grow herbs, fruit, and vegetables and produce olive oil, wine, and limoncello – offering guests a true taste of slow, sustainable Italy. Sarah is an Untold Italy tour host in Umbria, works on tour planning and logistics, as well as bringing her skills and experience of living in Italy for decades to Trip Consultations.

You can find La Cuccagna on these channels:

About our guest – Cassie Tresl

Cassie, her husband Alex, and their daughter Emmy make up ACE, a Seattle-born family proving that adventure doesn’t stop when you have kids. After moving to Europe in 2019 and traveling across the continent by car, they’ve embraced life on the road – from short getaways to months-long journeys.

Now based in Abruzzo, Italy, the family continues to explore hidden corners of their new home through budget-friendly road trips, giving Emmy the chance to grow up immersed in Italian culture and language while creating unforgettable travel memories together.

Living in a small town in one of Italy’s lesser-known regions, Cassie has become an expert in navigating the country’s travel logistics and uncovering hidden gems – expertise she now shares through her trip consultations and building content in the Untold Italy app, super-useful for independent travelers.

Follow Cassie here

Italian places, foods and concepts mentioned

Places

Assisi – hilltop town in Umbria, famous for St Francis
Corniglia – part of the Cinque Terre, but not directly on the sea
Abruzzo – region in central Italy
Lake Como – one of the northern lakes, known for its beauty and as a glamorous destination

Words / Concepts

Contiki – tour company, still offering group tours to Italy and Europe today, like their Simply Italy tour
St Francis of Assisi – the patron saint of ecology and animals, hailing from the 13th century, he founded the Franciscan order

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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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Episode #297: How to Travel Italy Your Way – Insights From Our Experts