Episode #283: Vespa Sidecars, Rooftop Bars, and Medieval Towns

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Listen to “283. Vespa Sidecars, Rooftop Bars, and Medieval Towns: Katy’s Italian Trip Highlights” on Spreaker.

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What do you get when you blend Roman rooftop bars, a Vespa sidecar adventure, dreamy medieval towns, and the rolling Umbrian countryside? For Untold Italy founder Katy Clarke, it’s just another chapter in her ongoing love affair with Italy. Her latest trip to Rome, Naples, Umbria, to newly discovered gem Urbino, and beyond – offered a mix of history and culture, delicious food, beautiful scenery, and heartfelt moments to inspire those dreaming of authentic Italian adventures.

Contents

Summary

In this episode, host Katy Clarke takes us along on her whirlwind journey through Rome, Naples, Orvieto, and Urbino. From sipping cocktails on Roman rooftops and zooming around the Eternal City in a Vespa sidecar, to uncovering the magic of medieval towns and taking refuge in the serene Umbrian countryside, Katy shares her firsthand experiences, travel tips, and fun mishaps – like surviving the summer heatwave, mastering Italian trains, and the art of finding bliss in a simple truffle omelette.

What you'll learn in this episode

On this trip, Katy combined business, team-building, and exploration while reconnecting with the Untold Italy team and families
Katy and the extended Untold Italy family celebrated with a rooftop party in Rome’s Trastevere
Navigating Rome during a heat wave – keep hydration, pace yourself and never forget good footwear
The team took a fun Vespa sidecar tour and joined a pizza and supplì class with a MasterChef Italia contestant
Katy visited Villa Farnesina for Raphael frescoes and a peaceful cultural break from the hot and busy city
Some of the team joined Katy on a day trip to Naples by high-speed train to experience its vibrant energy and street life
Joined a local guide in Naples for personal stories, food tastings like pizza fritta and discovered local culture and the art installation at the cathedral
Returned to Rome with travel tips including train logistics, luggage advice, and navigating Termini station (and the lack of taxis)
Katy joined the Untold Italy small group tour in Umbria, featuring repeat travelers and immersive local experiences
She enjoyed a deeper dive than previous visits in Orvieto with a local guide, sampled truffle pasta and iced coffee, and enjoyed its calm atmosphere compared to some of the touristy Tuscany towns
Visited a ceramics workshop in Deruta and soaked in views from their hotel over to Assisi
At La Cuccagna agriturismo near Gubbio – run by Untold Italy's own Sarah and her husband, Sal. Katy enjoyed the peaceful countryside, home-cooked meals, and met a podcast listener
Katy and Sarah took a day trip to Urbino, in Le Marche, with impressions of its medieval charm, artisan crafts, and hilltop architecture. Definitely off the beaten path, but worth it
Katy reflected on the contrast between city and rural travel and encourages everyone to visit lesser-known destinations in the Italian countryside for a deeper experience

Timeline Overview

03:16 Katy's feet are back on the ground in Italy – team bonding adventures in Rome
06:22 Dealing with the heat in Rome and thankful for the smaller visitor numbers in Centro Storico
12:40 Roman cooking class – Suppli and Pizza with LivTours' new cooking school
14:02 Naples day trip exploration with a WithLocals customizable guided city tour
22:55 Catching up with the Untold Italy tour in Umbria
25:18 Unique Assisi experiences in Umbria
32:52 Exploring Urbino’s Medieval streets, charm and artistic curiosities
35:50 Magic nights at La Cuccagna – you can't beat the Umbrian countryside

Italian places, foods and concepts mentioned

Places

Trastevere – district in central Rome, south of the Tiber, with a great vibe and gorgeous surroundings
Tonnarello – popular restaurant with a few locations in Trastevere
Mercato Trionfale – market in the Prati district of Rome, near the Vatican
Palazzo Farnese – high Renaissance building in Rome. Given to the French government in 1936 – still currently the French Embassy. You can visit, but only as part of a pre-arranged guided tour
Spaccanapoli – the street that is like the spine of Naples' center
Galleria – grand 19th-century shopping arcade in Naples
Orvieto – lovely Umbrian hilltop city
Deruta – Umbrian hilltop town, known as the center of maiolica ceramics manufacturing, as well as being an I Borghi più belli d'Italia (the most beautiful villages of Italy)
La Cuccagna – the agriturismo of Sarah, Untold Italy team member and podcast guest and her husband, Sal
Urbino – small city in Le Marche
Gubbio – city in Umbria, located on the lowest slope of Mt. Ingino, a small mountain of the Apennines, where you will find the birdcage cable car – the stuff of height-hating Katy's nightmares
San Saba – ‘little Aventine' is a district in Rome between Circus Maximus and Testaccio

Food / Drink

Suppli – Roman version of fried, stuffed rice balls with only mozzarella as the stuffing
Pizza Fritta – the deep-fried original pizza from Naples
Shakerato – refreshing iced coffee

Words / Concepts

Bared – Australian footwear brand
LivTours Vespa Sidecar tours – fabulous tour offered as Semi Private or Private experience
LivTours home made suppli and pizza cooking class
WithLocals – a great resource to find guides, as Katy did for her team's visit to Naples with Mariarosaria
Untold Italy Umbria Tours – our Umbria small group summer tour, Katy joined for a visit this trip. There are also tours in Fall/Autumn
The Ducal Star – a geometric ornament based on a mathematical design, which is a prominent symbol of Urbino's Renaissance heritage. The design, dating back to the 1400s, is found in various forms, including glass lampshades and embodies the intellectual and artistic achievements of Urbino during the Renaissance

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Experiences, Podcast episodes

Episode #283: Vespa Sidecars, Rooftop Bars, and Medieval Towns – Katy’s Italian Trip Highlights