203. New Italian Adventures to Try  In 2026

203. New Italian Adventures to Try In 2026

Author: Clever Dog Digital January 7, 2026 Duration: 34:50

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Links for the Show:

Fondazione FS Italiane

National Railway Museum

Strada dell’Olio DOP Umbria 

Via di Linari

In this episode, Kimberly Holcombe and Tommaso share insights from their friends who recently traveled to Italy during the Christmas holiday. They discuss historical train routes, exciting activities like driving a Ferrari through Tuscany, and adventurous hiking and biking options. Join us in this episode for unique ways to experience Italy beyond the typical tourist paths.


Key Points:

Christmas in Italy:

  • Venice was less crowded than Rome during the holidays.
  • Italian locals gather in Rome for Christmas, making it more crowded.
  • Venice had crowds during specific events like the Santa Claus gondolier parade.

Uber Black in Rome:

  • Friends used Uber Black successfully in Rome, despite previous reliability concerns with standard Uber.
  • Uber Black offers larger, luxury vehicles with professional drivers.

Historical Exploration:

  • Friends regretted not researching the history of Italian landmarks before their trip.
  • Tommaso suggests spending ample time before the trip researching historical facts so they are better prepared once there.

New Travel Options for 2026:

Historical Train Journeys:

  • Italy’s historic railways, managed by La Fondazione FS Italiane.
  • Binari Sensa Tempo (Timeless Tracks): Offers dozens of itineraries across the country.
  • The National Railway Museum is in Pietrasara, outside Naples.
  • The Christmas Market Train (Treno de Mercantini di Natale) runs from Sulmona to Roccaraso in Abruzzo.
  • A day-long excursion from Torino to Canelli offers wine tastings in Piemonte.
  • The train features Centoporte (100 Doors) carriages from the 1920s to the 1980s.

  • Sommeliers offer tastings of regional wines like Barolos.


Olive Mill Trains:

  • Frantoi Aperti (Open Olive Mills) trains run every weekend through mid-November.
  • Organized by Strada dell’Olio DOP Umbria (The Olive Oil Road).
  • Visitors can taste fresh extra virgin olive oil and learn about production.
  • Guided tastings led by professional tasters are available on board.
  • The route runs from Arezzo to other Umbrian towns like Spoleto and Assisi.
  • Promotes mindful travel and reduces carbon emissions.

Luxury Driving:

  • Drive a Ferrari through the hills of Tuscany.
  • Prices are around 4,000 euros per day, or 2,000 euros per person for two.
  • Multi-day excursions include high-end hotels.

Adventure Hiking:

  • Via Di Linari: An ancient 93-mile trail through medieval monasteries, abbeys, and a national park.
  • The trail snakes through Emilia-Romagna and the Apennine Mountains into Tuscany.
  • Best hiked in spring or fall, taking about nine days to complete.
  • Sections are no more than 12 miles long.
  • The website Camini Emilia Romagna provides detailed itineraries and accommodation options.
  • Monasteri Aperti: Monks open their doors to hikers for hot meals on certain autumn weekends.

Biking Expeditions:

  • Flat, scenic rides connecting food capitals like Parma and Bologna to Venice.
  • Explore historic sites like Ferrara, a UNESCO World Heritage site.
  • Sardinia: Features rugged coastlines and routes for all levels.
  • Sicily: Combines history and natural beauty, with cycling through the Valley of the Temples and around Mount Etna.
  • Egadi Islands (Isola Egadi): Offers idyllic cycling vacations.
  • Isola di Levanzo is ideal for mountain bikers.
  • Isola di Favignana has paved roads and gravel paths.
  • Isola Marettimo is for serious mountain bikers, featuring a small idyllic village.


There's a particular magic to Italy that goes far beyond its famous landmarks, a rhythm of life that you only really start to feel once you've lingered in a local piazza or navigated a bustling market. Kimberly's Italy Travel is an invitation into that deeper experience, guided by Kimberly Holcombe, whose own story began with a life-changing move to Milan years ago. That journey didn't just create memories; it reshaped her perspective, and she shares that genuine, lived-in understanding in every episode. You'll hear personal stories from her travels, often punctuated by the kind of comical, real-world lessons that no standard guidebook ever mentions. This podcast serves as a rich audio companion, weaving together passionate discussions about regional cuisine, layers of local history, and the vibrant arts that define Italy's culture. It’s about the sensory details-the taste of a perfectly simple dish, the echo in an ancient alleyway, the warmth of a conversation with a new friend. Listeners gain practical, invaluable travel tips born from direct experience, all while feeling like they're sharing a coffee and a laugh with a knowledgeable guide. Through these conversations and reflections, the aim is to transport you, offering not just a list of destinations, but a feeling for the places and people that make Italy endlessly captivating.
Author: Language: English Episodes: 50

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