Tuscany Itinerary

Day 1Welcome to Tuscany

Upon arrival at Terontola railway station, you will be met and transported in a luxury minivan the short distance to our base in the town of Cortona. On our way from Terontola, we get our first sight of Cortona, red terra-cotta roofed buildings nestled on the hillside in front of us. At Cortona, you will be checked into your luxurious Tuscan style hotel which will be home for the duration of the tour.

Cortona received a great deal of attention and fame following the publication of Frances Mayes’ bestselling novel ‘Under a Tuscan Sun’ and the movie of the same name in which Diane Lane portrays Mayes’ relocation to Tuscany and her restoration of the beautiful villa, ‘Bramasole’, just on the edge of Cortona.

The town is filled with beautiful time-worn stone buildings dating back as far as the 13th century housing museums, galleries, artists’ studios, restaurants, b&b’s, boutiques, handbag and shoe stores with narrow cobblestone laneways winding between them. Cortona also has a wonderful selection of restaurants many of which we will be visiting for our evening meals, and not to be missed are the mouthwatering gelato shops.
After time to freshen up and settle in, you’ll be invited to meet the other guests over a glass of the local vino, a cheese platter and a short briefing session. We will then start exploring the local area by taking a short drive to the edge of town for a quick look at Frances Mayes’ Bramasole and then up to the top of the hill to the magnificent fort that towers over Cortona, offering panoramic views far out over the Tuscan countryside.
Upon return to our hotel there will be time to relax and refresh before our first night welcome dinner.​​​
Day 2Cortona

On our first full day of the tour we take the opportunity to more thoroughly explore our surroundings in Cortona at a leisurely pace. The village centre is filled with art galleries, boutiques, shoe and handbag stores, leather artisans, and gelato shops. The town square is always humming with activity and the cafes and restaurants have a great view of the passing parade.

Today we will visit sites of historical significance; visually spectacular and spiritually refreshing. The beautiful Santa Maria della Grazie was a challenge to engineers to build a place of worship at this site of miraculous healings and now sits as a landmark on the hill below Cortona. Also on the outskirts of the town is Santa Maria Nuova, another beautiful example of the gothic architecture in the area, and amidst a beautiful hillside setting we visit the tranquil Franciscan monastery Eremo Francescano La Celle, one of the most peaceful and spiritual places in all of Italy.
We will then head back into the heart of the old town for a visit to the acclaimed MAEC Etruscan Museum before taking a relaxed lunch at a special restaurant we know of.
Following lunch with the group you will have time to explore the old town of Cortona by yourself to visit the sites, museums and galleries or to do a spot of shopping at the boutiques as you please.
After a day spent exploring Cortona, we will gather again as a group to dine at an intimate little restaurant just down from the main piazza where we’ll enjoy fine Tuscan food and swap shopping stories.
Day 3Assisi - Basilica Tour

Pont de Avignon
Today, we head further afield, taking a drive to Assisi, which is situated in the neighbouring region of Umbria, Italy’s ‘Green Heart’. Umbria is located in the very centre of Italy, not having any coastline but containing within its borders the splendid waters of Lake Trasimeno in the northwest of the region. The typical Umbrian landscape spreads out before us in waves of agricultural fields patchworked over the rolling hills with rows of slender, tapering cypress trees defining the roads through the region.

Assisi is of course famous as the home of Saint Francis, patron saint of Italy, and recognition of this can be seen throughout the city including the magnificent 13th century Papal Basilica of San Francesco d'Assisi located at one end of the city on the hillside of Monte Subasio overlooking the panorama of the Umbrian valley.
Upon arrival at Assisi we will familiarise ourselves with the layout of the city, taking in the sights of the Cathedral of San Rufino (13th century) where Saint Francis was baptised and the Ancient Roman ‘Tempio di Minerva’ that now houses the Santa Maria sopra Minerva, built in the 16th century as we walk through the piazzas to the Basilica San Francesco d’Assisi. At the basilica we will take part in an audio tour to guide us through the magnificent rooms and frescoes of one of the most visited religious sites in all Italy.
Following our visit to the basilica we will have lunch in one of Assisi’s finest restaurants offering Umbrian style cuisine in a beautiful setting with transparent floors looking into an Etruscan archaeological site.
After our lunch we’ll take some free time to explore the city where the streets are filled with small shops selling all sorts of delicacies and wine shops offering up many of the local vintages as well as plenty of opportunities for clothing, trinkets and of course, religious souvenirs.
At the end of the day we head back to Cortona where refreshments will be waiting for us. Later in the evening, we’ll get together for a light dinner and an early night for a well earned rest.
Day 4Montepulciano and Pienza

Travelling south from Cortona through the rolling vineyards we visit the mediaeval hilltop town of Montepulciano, famous for it's wines and its history. Stopping first just outside the city at the high renaissance chiesa of San Biagio di Montepulciano before driving up the hill to enter the old part of the city near the Fortezza Medicea di Montepulciano.

Montepulciano was originally an Etruscan settlement and during the Middle Ages was fought over by Siena and Florence until finally coming under the banner of Florence permanently in 1404. This history has left the town with a fascinating mix of gothic and renaissance architecture. The history of wine in Montepulciano dates back just as far with Etruscan pottery showing traces of the culture.
The main piazza at the top of Montepulciano is Piazza Grande and this charming square is lined with restaurants, cafes and specialty shops where we will have time to explore and sample some of the local product before stepping down through an entryway below Palazzo Ricci to find ourselves in an underground wine cellar that has been awarded the title of ‘Most Beautiful Wine Cellar in the World’ where many thousands of hectolitres of Vino Nobile are stored for aging and where we will be taken on an informative tour of the cellar complete with wine tastings to be followed by a light lunch in the ‘cantina’.
After lunch we will have time to explore some of the shops and sights of Montepulciano before traveling the short distance to Pienza , another hilltop town famous for pecorino sheep cheese and spectacular views where we will wander through the picturesque streets of this beautiful village taking time to investigate the local shops, giving us the opportunity to sample some of Southern Tuscany’s traditional products, including Pecorino di Pienza and Extra Virgin Olive Oil.
Following our visit to Pienza we head back to Cortona once again for a short rest and a chance to freshen up before dinner in a wonderfully friendly atmosphere at one of our favourite local restaurants.
Day 5Arezzo - Market Day

Today is all about the markets, and just a short distance from Cortona, the vibrant city of Arezzo, famous for frescoes by Renaissance artist, Piero della Francesca, holds a colourful market every Saturday selling local produce as well as all manner of manufactured goods and textiles and the food vendors have so many treats and sweets that it’s almost impossible to choose.
Arezzo is also home to many fine boutiques and fashion stores interspersed with historical buildings, towers and churches. It is where we discover such treasures as La Favola Mia Arezzo, a textile and gift store that creates the most amazingly beautiful artworks out of linen, conveniently located halfway up the hill to the Duomo and only a couple of blocks from the medieval abbey, Badia delle Sante Flora e Lucilla that dates back to 1278 but was rebuilt in the 16th century to the design of Giorgio Vasari and houses works by Segna di Bonaventura, Bartolomeo della Gatta and Andrea Pozzo.
Of course, after a busy morning at the markets, we will enjoy lunch in a quiet atmosphere not far from these fabulous sights.
After lunch we will still have time to explore some more of the city before heading home to Cortona where you will have time to relax or wander through the town before preparing for another special dinner treat at a gorgeous villa not far from Cortona.
Day 6Perugia

Today we head back into Umbria, visiting the capital, Perugia. This compact hilltop city dates back to the 6th century BC and is rich with history and culture with many well preserved archaeological sites including the city gate and walls.
For a special dose of culture we visit the Galleria Nazionale dell'Umbria, one of the richest and most diverse collections in Italy, containing a comprehensive and complete collection of Umbrian art with sections dedicated to textiles, ceramics, jewellery and ancient graphics, including various masterpieces from the Middle Ages and Renaissance, with works by Arnolfo di Cambio, Nicola and Giovanni Pisano, Duccio di Buoninsegna, Gentile da Fabriano, Beato Angelico, Benozzo Gozzoli and Piero della Francesca.
Perugia is also a university city with lots of modern culture and life intermingling with medieval heritage.
We’ll take our lunch in a restaurant located in one of the oldest palazzos of Perugia that now houses a beautiful four star hotel.
Following our lunch we’ll have free time to explore some more of the city or visit some of the beautiful boutiques and fascinating shops before journeying home where we can prepare for another special surprise evening.
Day 7San Gimignano
On Monday morning our first destination is the delightfully authentic medieval town of Monteriggioni where it is possible to walk along the fortified walls that surround the village offering spectacular panoramic views. We will also visit the small museum in the village that contains displays of medieval weaponry where you can actually try on some armour!We then continue our journey to San Gimignano, ‘city of the beautiful towers’, the UNESCO World Heritage listed medieval city famous for the lofty towers built by competing wool merchants to display their status and wealth. Our first stop will be for lunch on the terrace of one of San Gimignano’s best restaurants where you will have the opportunity to sample the renowned Vernaccia di San Gimignano wine. After lunch we will explore this rich and vibrant city.
San Gimignano thrived during medieval times, becoming a trading centre due in part to its location along the Via Francigena. Entering the walled city is like taking a journey back to the 13th century with many buildings well preserved from that time; 14 of an original 72 towers still survive today. The market square in San Gimignano is a bustling cultural centre lined with cafés and street entertainers. We will have the opportunity to visit the Palazzo Comunale which houses some beautiful frescoes: "Virgin and Child" by Lippo Memmi and frescoes inspired by chivalry and courtly pursuits by Azzo di Masetto illustrating medieval lifestyle.
For those who are feeling energetic and adventurous an uphill walk to the Rocca di Monte Staffoli, where the ruins of a fort now contain a museum, you will be rewarded with breathtaking views over the city.

Following our day at San Gimignano and a sleepy ride home we will enjoy a special treat at one of Cortona's cosiest restaurants, just off the piazza around the corner from our hotel, for a delicious Tuscan style meal and a few laughs to round out the day.
Day 8Orvieto - History and Majesty

Located in the heart of Umbria, perched atop a spectacular volcanic rocky plateau is the city of Orvieto; a natural fortress protected on all sides by sheer cliffs. The rock of Orvieto has been an important settlement for civilizations since the 8th century BC when the Etruscans regarded it as their most important town, and remained an Etruscan stronghold until the 3rd century BC when the Romans finally conquored the city.
During the 13th Century AD as a result of the civil war in Rome, Pope Urban IV lived in Orvieto, constructing a papal palace and commissioning the Duomo.

Evidence of the Etruscan occupation can be seen in archeological excavations under the predominantly medieval buildings that are seen in Orvieto today, and much of the construction from the middle ages is still in use, for example the beautiful entrance to the city, Porta Maggiore.

The city is now divided into four quarters: Corsica, Serancia, Olmo and Santa Maria della Stella. Our guided tour today will take us to some of the most important and beautiful sites and monuments in Orvieto; places like San Giovenale, one of the oldest churches in all of Umbria that was built in 1004 on top of the former Etruscan temple. Perhaps the most majestic of Orvieto's sights is the Duomo, commissioned by Pope Urban IV in 1290, taking several hundred years to complete standing proudly in the Piazza del Duomo at the centre of the city. The Duomo houses many treasures and relics, among them the stunning frescoes by Luca Signorelli adorning the San Brizio chapel.

Elsewhere in the city you will find the San Franscesco church where Pope Boniface VIII was canonized by King Louis IX of France in 1297 as well as numerous palaces owned by the noble families of Orvieto and the architecturally unique Pozzo di San Patrizio with its amazing double helix stairways that never meet!

To round off our day of magnificent sights we will dine overlooking the valley from another of Cortona's fabulous restaurants.
Day 9Cortona, Castiglion Fiorentino - Olive Oil/ Balsamic/ Wine Tastings and Tour

Mill Press
Today is all about experiencing the flavours of Tuscany at the elemental level: the products of the olive and the grape, selected and cultivated to create unique sensations. These experiences are offered to us by some equally unique people who are passionate about creating exceptional products.

Our first visit is with a producer of olive oil and balsamic vinegar who has acquired olive groves comprising ancient trees whose fruit produces an oil of unique depth of flavour. In addition to the olive oil tasting we will also be treated to a palate awakening and mind changing sampling of flavour infused balsamic vinegars. Whilst the thought of vinegar tasting may not sound overly appealing at first, the taste sensations created by these hand-crafted balsamics is absolutely amazing and not to be missed.

With our taste-buds on high alert after our olive oil and balsamic tastings, we will stop for a simple lunch in Cortona where we can compare tasting notes and plan an assault on some of the local shops this afternoon. Following lunch we will have time to become more acquainted with the village of Cortona or simply relax for a couple of hours before setting out for our next visit later in the afternoon.

Taking a short drive north from Cortona we will arrive at the estate 'Casali in Val di Chio', home to a family owned and operated winery and Tuscan resort. The estate is key part of the local region's history and still plays an important role in the community. The story of this family's persistence and passion is truly inspirational.

We will sample the hospitality of the estate, being given a tour of the winery and the estate that includes a formal tasting of their wines, a chance to relax in the grounds with a cool drink or a café, or perhaps to display your skill in a game of pétanque before gathering for dinner created using produce harvested from the estate's own organic gardens. This is an ideal opportunity to engage with the locals in a delightful and relaxed environment.
Day 10Siena Guided Tour / Shopping

Today we travel west to Siena. Located at the very heart of Central Tuscany, Siena is a vibrant city filled with history and culture where the landscape has remained identifiable for hundreds of years. Formerly a long time adversary of Florence during medieval times, the hilltop city of Siena has a proud tradition of independence and today we’ll be shown around by a local guide who will educate us on some of the city’s background and take us to some of the historic sights. Siena, like Florence has a great deal to see compressed into a small area which makes it possible to visit many of the attractions on foot.
Some of the world famous sites of Siena we visit include the masterpiece of Gothic - Romanesque architecture, the Duomo built in the 13th century to be ‘the greatest monument to Christianity’, home of the famous Piccolomini Library and bearing work created by artists such as Pisano, Donatello, della Quercia, Michelangelo, and Bernini. Not to be missed is the spectacular Piazza del Campo, which has been the heart of Sienese lifestyle since the late 13th century, and where the famous Palio horse race is still held on two special days each year, Movie lovers will recognise the piazza from the recent James Bond thriller, ‘Quantum of Solace’ as well as many other movies such as ‘Letters to Juliet’.
Upon arrival at Siena we will meet up with our guide who will show us around the city and take us for a visit to the famous Duomo.
After our morning tour, we have a lovely restaurant selected close to the Piazza del Campo where we can rest and refuel before continuing our exploration of Siena in free time. Following a full day’s exploration of Siena we will return to our hotel in Cortona to freshen up or explore the local area before gathering at yet another of our favourite restaurants for dinner.
Day 11Castiglione del Largo & Lake Trasimeno​

Our final day’s excursion takes us on the short trip to the shores of Lake Trasimeno and the village of Castiglione del Lago, where the remains of a fort overlook the waters of the lake and the beautiful village it protected. From Castiglione del Lago we take a ferry ride across Lake Trasimeno to Isola Maggiore, the second largest island in the lake, taking time to explore the small village and wander along the scenic pathways to several beautiful historic buildings. Isola Maggiore is only a small island but well worth the visit to experience the unique feel of this community.

We will return to the mainland for lunch in Castiglione del Lago at a beautifully renovated hotel where we can enjoy our meal with a backdrop of stunning views over Umbria.
Following lunch, we will take a tour of the village and the ruins of the fort and the museum before once again returning to Cortona to finish packing or just relax prior to our farewell dinner that forms part of a weekly event in Cortona to showcase the local food and wines in a festival atmosphere.
Day 12Depart

All good things must come to an end and today we must check out of our hotel in Cortona at 10:00 am and return to Terontola railway station to catch your train back to Rome, Florence or Milan to continue your adventures until next time.