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Journey along the less-traveled roads of Umbria, Tuscany, and Emilia and discover another side of Italy. Stroll Assisi’s historic streets, visit Florence, the “Cradle of the Renaissance”, and explore Emilia, a haven for food lovers and creatives. From Modena, home of Enzo Ferrari, to time-honoured traditions like Parmigiano-Reggiano and balsamic vinegar, savour regional flavours whilst uncovering Italy’s legacy of design, culture, and the music of Luciano Pavarotti.
Designed for travellers who want to go beyond checking off a list, this small‑group journey makes it easier to step into daily life, share conversations with locals, and immerse yourself in each destination.
*Advertised price based on 10 November 2027 departure and correct as of 26 October 2026.
Inclusions
Roundtrip home to airport Private Chauffeur Service
16 meals: 10 Breakfasts, 5 Lunches, 1 Dinners
4 Handpicked Accommodation including 3 nights in a traditional Tuscan villa
Cultural Experiences
Hunt for truffles with a local expert and his truffle-sniffing dogs.
Enjoy three nights in a restored Tuscan villa.
Visit Pavarotti's home and museum and explore his connection to opera and music.
Culinary Inclusions
Experience a home-cooked meal in one of Umbria's country homes.
Savour the famous Chianti red wine during a tasting at a winery in Tuscany’s rolling hills.
Tour a traditional Parmigiano-Reggiano dairy and enjoy a tasting.
Must-See Inclusions
Explore Assisi, the historic birthplace of St. Francis.
Discover Florence, the "Cradle of the Renaissance."
Visit the Ferrari Museum, showcasing iconic design and innovation.
Highlights
Rome
Assisi
Home-Hosted Lunch
Truffle Hunting
Olive Oil Tasting
Tuscan Villa Stay
Chianti Wine Tasting
Florence
Ferrari Museum
Pavarotti's Home
Parmesan Cheese Experience
Balsamic Vinegar Producer
Itinerary
Day 1: Rome, Italy
Accommodation: Kolbe Hotel Rome
Italy’s dynamic capital city beckons. As arrival times will vary, there is no scheduled sightseeing today. Spend the day as you wish, exploring independently. As evening approaches, get a taste of local culture with an aperitivo — a relaxed tradition of small bites and drinks that offers an easy way to unwind at the hotel and get to know your fellow travellers.
Day 2: Rome - Narni - Umbria Region
Accommodation: Hotel Dei Duchi
Meals: Breakfast
This morning, transfer to Umbria. Visit the hill town of Narni and step into a long-forgotten world as you explore an archaeological site hidden beneath the village. Moving through atmospheric chambers, frescoed rooms, and historic passageways, uncover the stories behind this lost world. In the afternoon, continue through a landscape of olive groves and cypress trees on your way to your hotel. Enjoy the peaceful rhythm of country life in a pristine Umbrian town, your home for the next three nights.
Day 3: Umbria Region
Accommodation: Hotel Dei Duchi
Meals: Breakfast, Lunch
Travel to Assisi, the birthplace of St. Francis. Set out on a walking tour of the old city with a local guide, learning about its history as you stroll the medieval streets. Visit the famous Basilica of St. Francis and admire Giotto’s frescoes. Later, a local family welcomes you to their country home for lunch as their honoured guest. Share stories and make an Umbrian friend (or two).
Day 4: Umbria Region
Accommodation: Hotel Dei Duchi
Meals: Breakfast, Lunch
In the shadow of the Apennines, discover the flavours of Umbria’s renowned culinary heritage. Join a local truffle hunter in search of the elusive fungi in the company of his trained, truffle-sniffing dogs. Sample the goods yourself during a rustic, home-cooked lunch before returning to your hotel in the late afternoon.
Day 5: Umbria Region - Chianti Region, Tuscany
Accommodation: Villa San Lucchese
Meals: Breakfast, Lunch
Take in views of Lake Trasimeno and pause at a family-owned frantoio (olive press), where olives are pressed each November. After learning about the many varieties of trees and traditional oil-making methods, roll up your sleeves and join in for a cooking class of Umbrian specialities doused in their oil and accompanied by a hearty lunch. In the afternoon, drive through the Chianti countryside to a restored Tuscan villa where your hotel is located.
Day 6: Chianti Region, Tuscany
Accommodation: Villa San Lucchese
Meals: Breakfast, Dinner
Spend a quintessential Chianti day exploring the legendary rolling hills of Tuscany, covered in vineyards and olive groves. Countryside backroads lead you to an artisanal pasta factory in the village of Greve, as well as a family-owned winery producing Chianti Classico. Visit the historic cellars before sampling their wines during a tasting accompanied by local cheeses and charcuterie. Return to your hotel in the late afternoon. As the sun begins to set, gather with your fellow travellers for a dinner of Tuscan specialities.
Day 7: Chianti Region - Florence
Accommodation: Villa San Lucchese
Meals: Breakfast
Explore Florence, the “Cradle of the Renaissance.” Today, it’s your choice! Join a local expert for an extensive walking tour of the city’s highlights -OR- visit the Ferragamo Museum, celebrating Italy’s enduring influence on global style. Take some time on your own to explore the city’s seemingly endless treasures, before returning to your Tuscan villa in the evening.
Day 8: Chianti Region - Reggio Emilia
Accommodation: Hotel Posta
Meals: Breakfast, Lunch
Begin your day travelling through the Apennine Mountains, crossing into the Emilia region, a haven for food lovers and creatives. This afternoon, visit the countryside home of the great opera singer Luciano Pavarotti. Tour the rooms that were once his residence, still filled with family heirlooms and mementos from his legendary career. Your visit concludes with a private opera concert where vocalists-in-training perform some of the Maestro’s favourite arias. Afterwards, continue to Reggio Emilia, your home for the next three nights.
Day 9: Reggio Emilia
Accommodation: Hotel Posta
Meals: Breakfast
This morning, visit Modena, the hometown of Enzo Ferrari. Explore the Ferrari Museum showcasing vintage vehicles, several famous engines, and a multimedia presentation before spending some time in the old town. Return to Reggio Emilia mid-afternoon. Before settling in for an evening at leisure, explore the town and visit the historic hall where Italy’s three-coloured national flag was created.
Day 10: Reggio Emilia
Accommodation: Hotel Posta
Meals: Breakfast, Lunch
Early this morning, visit a local dairy producing Parmigiano-Reggiano cheese according to traditional codes dating back to the 1300s. Then, pause at an agriturismo where the owners still age their balsamic vinegar production in the attic, as countless generations have done before them. After a tasting and light lunch, return to Reggio Emilia for an afternoon at leisure. This evening, come together for a toast to the memorable journey you’ve shared.
Day 11: Reggio Emilia - Tour Ends
Meals: Breakfast
Your journey through the flavours of Italy comes to a close today.
Booking terms and conditions apply.
*
Term and conditions apply: All pricing subject to change and availability. Advertised prices are per person twin share unless stated otherwise. Offers may be withdrawn at any time. Itineraries are subject to change. Booking Conditions and Phil Hoffmann Travel Schedule of Professionalism* applies. Please speak to your Phil Hoffmann Travel Consultant for more information.