Itinerary Summary
JOURNEY THROUGH UMBRIA – 10 NIGHTS, 11 DAYS
DATES: SAT 9TH MAY – TUES 19th MAY, 2026
Or 7 Night Option Sat 9th May - Sat 16th May, 2026
Day 1 – Todi
Morning pick up from Hilton Hotel Fiumicino Airport and transfer to Todi. A welcoming outdoor lunch at one of Todi’s best trattorias with expansive views over the Tiber Valley.
We meet our professional local guide Elisa, to show us the highlights of her charming home town with narrow cobblestone streets, medieval buildings and fascinating history. There will be some free time to explore on your own.
Then it’s a short drive to our luxurious villa for the week, Podere Masale. A magnificent restored villa that has large rooms and beautiful outdoor spaces.
Tonight, we can unwind as we have a menu especially created for you by our wonderful friend and cook Francesca. Relax into the hospitality of Umbria as you sample local culinary delights and beautiful wine whilst enjoying the views of the green rolling hills.
Day 2 – Civita di Bagnoregio
We enjoy our fresh produce breakfast at the villa before heading to the fairy tale village of Civita di Bagnoregio. This tiny medieval hamlet is perched above a rock on the hill, only accessible by footbridge. It dates back to the 6th Century BC and time of the Etruscans.
We visit the museum to get an understanding of the incredible natural formation of this town and appreciate the enormity of keeping this village alive. Free time to wander through this picturesque town with spectacular views.
Lunch at a long standing family run outdoor restaurant serving traditional yet modern cuisine and local wines. We return to the villa for a rest and relaxation.
We take a short drive to dinner to enjoy another picturesque setting and memorable meal by a re-known local chef.
Day 3 – Orvieto
After another relaxing breakfast, we’ll be off to explore the magnificent medieval city of Orvieto. Our professional guide will help us learn more about Orvieto’s architectural beauty and cultural heritage. These include major sites such as the majestic cathedral Duomo di Orvieto, Pozzo di San Patrizio (St Patricks Well) and the Piazza del Popolo.
We’ll also learn about the fascinating ancient underground world: a maze of tunnels and caves.
Another lovely Umbrian meal with allow us a break to then have free time to wander this favourite village with free time in the afternoon. It’s great for shopping!
We enjoy the evening at the villa, being treated to a modern Umbrian meal prepared by one of our professional local chefs.
Day 4 – Cooking Class & Deruta
Today we start with a traditional cooking class. We’ll spend a few hours cooking with Francesca in her Umbrian country house discovering the secrets behind her delicious meals. It’s a fun and educational experience where you get rewarded by consuming your creations coupled with local wines.
After lunch, we will return to the villa for a short rest. We shall head out in the late afternoon to Deruta, home of Italian ceramics and pottery. Its medieval streets and artisan workshops tempt you to buy that little special piece to take home!
We finish the evening with a real treat. We dine at Ristorante i Rodella, a Michelin star dining experience perched just on the outskirts of town.
Day 5- Montefalco & Rest
We’re off to Montefalco, in the heart of wine country where sagrantino grapes have thrived on these fertile plains since Roman times. Our destination is a leading winery where we discover some great Umbrian wines; the renowned Arnaldo Caprai estate. A Wine Educator will lead us on a tour of the estate, from the vineyards to the cellar, discovering what’s involved in making good wine, from fermentation to ageing and bottling with some opportunities to sample all the produce, naturally!
After our tour, we will head back to the villa for a well deserved rest afternoon.
Tonight, we are treated to dinner and wine in a local home where the host has written best selling cook books and appeared on Italian TV. Her fourteenth century home and expansive rose garden is an absolute experience in itself. This is one of my favourite nights on tour, true Italian hospitality!
Day 6 – Spoleto
We enjoy relaxing at the villa this morning to catch our breath. We shall share a light lunch at the villa before heading out to explore the medieval town of Spoleto in the afternoon.
There we explore the incredible Albornoz Fortress, Duomo di Spoleto, and Ponte delle Torri with our professionally guided walking tour. It's a steep town but with the help of a range of escalators, this makes it easy to get up the top!
Some free time in the late afternoon followed by a magnificent dinner at one of our favourite restaurants.
Day 7 – Gubbio
It’s a big day today as we’re off to Gubbio after breakfast. Our May guests will attend one of the biggest events on the Gubbio calendar: the Festa dei Ceri. This centuries-old tradition takes place each May 15th, the eve of the Feast of Sant’Ubaldo, the town’s patron saint. It centres on carrying three enormous wooden structures – ceri or candles - each some 5m tall and weighing several hundred kilograms. It’s an adrenalin filled day, an unforgettable authentic experience.
We enjoy lunch in Gubbio and a little free time to explore and shop.
We then head back to villa late in the afternoon for a pizza party with our Pizzaiolo Ciro, using the antique pizza oven on the villa's grounds.
Day 8 – Spello
We check out of the villa after breakfast today. We then head off to visit the quaint village of Spello.
We take a scenic walk along the poppy saturated Roman Acquaducts, with a local friend who tells us the history of the water system. The walk offers spectacular views of the local town, overlooking old olive groves. A magical walk in nature.
We then head into the historical centre to enjoy a light lunch and free time to wander through Spello, one of the smaller hilltop towns, less crowded and very quaint. Spello is famous for its bright pots of colour, adorning many steps and entry ways of the local’s homes.
In the afternoon we make our way to our new accommodation in the medieval village of Assisi. We shall dine locally tonight in one of Assisi's top restaurants.
Day 9 – Perugia
We take a short drive this morning to Umbria’s capital, Perugia. As we head out on our privately guided walking tour , we discover Perugia’s history and breathtaking buildings. Perugia is a city that effortlessly blends historical charm, cultural richness, and modern vibrancy. After being educated on Perugia’s past and present, you’ll then have some free time to wander this town at your own pace.
We will enjoy a casual lunch at an establishment loved by the locals.
Perugia has a vibrant feel, lots of university students and amazing shopping.
We return to Assisi in the late afternoon for a rest and local gourmet dinner.
Day 10 – Visit Chiesa del Carmine
Enjoy your breakfast at the villa before we journey north to the beautiful property of Chiesa del Carmine for a very relaxing day! Chiesa del Carmine is the ancient church at the centre of the Carmine Estate, just 20 minutes north of Perugia and close to the Tuscan border.
We then discover the real, earthy taste of Umbria on our truffle hunt while we take in the beautiful scenery. You will be a led by our expert truffle hunter, his truffle dog and an English-speaking guide. After the hunt, it’ll be time for a truffle degustation lunch by an award-winning chef. Naturally, this will be paired with their award winning wines, expertly chosen by their sommelier. What an excellent way to relax and reflect on our week together!
We return to Assisi where we now have time to explore the well known sites on foot. Assisi is said to be the spiritual heart of Italy, beckoning with its timeless beauty, spiritual significance, and medieval charm. It’s internationally famous as the birthplace of St Francis, Italy’s patron saint.
A lovely final dinner to reflect on our amazing time together.
Day 11 – Check out at 10am
Today we say goodbye! We enjoy our last breakfast together. We will take you to your local departure point within Assisi - bus, train or care hire. We also offer a transfer back to Fiumicino Airport.