6 days

Taste of Tuscany

Self Drive

Day 1: Arrival in Tuscany

Pick up your car rental from your starting location and drive to Figline Valdarno, an arcadian oasis in the Tuscan countryside surrounded by vineyards and olive groves. 
Check in to your lovely accommodations. Villa la Borghetta.

This evening a reservation has been made for you at the fabulous Torre Guelfa restaurant in the town centre a short  drive from the hotel .  Here in the in restored 13th century halls of the restaurant  Chef Claudio Piantini will prepare an extraordinary culinary experience for you . The dinner will include Tuscan specialties accompanied by fine local wines from the impressive 1500 bottle cellar of the restaurant.

Hotel: Villa La Borghetta (or similar star rating hotel)

Day 2: Siena and San Gimignano

Today we suggest a visit to the medieval jewels of Tuscany, San Gimignano and Siena.
departure with English-speaking driver/host from your hotel for your full-day private excursion to visit the medieval towns of San Gimignano and Siena.

San Gimignano is famous for its towers. The city gained its prominence due to its location, rising from the hills of the upper Elsa Valley, facing the land of Volterra and positioned right on one of the most important stretches of the medieval via Francigena. It is one of the most charming and picturesque of all the Tuscan hill towns. The towers dominate the town in the manner of skyscrapers in our modern cities. At one time there were more than 70 towers, built as symbols of wealth and as a security precaution by the town's prosperous merchants, but only 14 remain today. Walk through the wonderfully preserved town square at the Piazza della Cisterna and visit the 13th century town hall - the Palazzo del Popolo. There are good views from the Rocca citadel and the entire town is an excellent place to stroll and soak up the atmosphere.

Continue to Siena .

Surrounded by olive groves and the vineyards of Chianti, you will move onto the town of Siena: one of the most beautiful cities of Tuscany. Set on three hills, the city is drawn together by winding alleyways and steep steps, while the Piazza del Campo stands at its heart, and the Duomo and St. Maria della Scala serve as additional cultural landmarks. Famed for the "Palio", the annual historic horse-races, it is also home to one of the oldest Universities in Europe, which ensures a vibrant Italian student atmosphere throughout the academic year. In addition to the bustling daily life of the streets and squares of the city, Siena offers many cultural events, concerts, cinema, theatre and a wide range of sporting activities.

Return to your accommodations in Tuscany in the evening.  

Day 3: Chianti Excursion & Cortona

Today after breakfast and checking out of your hotel, depart on an excursion to the famous Chianti wine region and continue to your accommodations in Cortona.  

You will make your way into the scenic Chianti Classico region.

This area is considered one of the oldest wine regions in the world, as evidenced by the medieval castles and ancient towns that line the hillsides.  One of the grapes (the Canaiolo nero) used to make Chianti predates the Roman civilization and was once known as the “Etruscan grape.” 

The name Chianti most likely was taken from a noble Etruscan family name, the Clantes.  In the 13th century Florence created the “Lega del Chianti” to unite the three most important areas, Castellina, Radda and Gaiole.  The black rooster became the symbol of the Lega del Chianti.

Driving along the Chianti road, you will reach the beautiful town of Radda, where your first stop will be the Medieval merchant square. Then, you will visit the famous Ceramic Rampini.

Continuing through the charming countryside, you'll discover a balsamic vinegar farm where a visit has been arranged. Finally, you will visit a local winery where you will enjoy a  wine tasting and a visit to the cellars.

Lunch at a local restaurant will be included.

After lunch continue to your next accommodations just outside the quaint town of Cortona.

Hotel: Villa Baldelli (or similar star rating hotel)

Day 4: Val D'Orcia excursion

This morning we suggest an excursion through the picturesque Val d'Orcia: Italy's 'Golden Valley'. This area's naturally beautiful landscape was sculpted during the Renaissance not only to meet agricultural needs but also to reflect the aesthetic sense of the period, and this concept has been maintained to the present day. Your first stop will be the small but fascinating town of Pienza, famous for the cheese, built almost entirely during the renaissance where we will witness one of the first examples of modern urban planning.

You will visit a local cheese laboratory to witness the traditional methods still used to produce high quality products. You will have a chance to taste the delicious cheese.

Continue to Montepulciano home of the famous Nobile wine, a mellow-flavored red with a mildly floral aroma and that features a distinctive iridescent orange tone. A wine tasting will be arranged for you.

Return to your accommodations in Cortona in the evening.  

Day 5: Cortona and Arezzo

Today a is a free day to enjoy at the villa or perhaps go into Cortona, the town made famous by the movie, "Under the Tuscan Sun".   

You may also want to take a drive over to Arezzo one of the wealthiest cities in Tuscany, it produces gold jewellery and clothing for shops all over the world. It is also the charming town seen in the award-winning movie “Life is Beautiful” with Roberto Benigni.

Return to your accommodations in Cortona in the evening.  

Day 6: Departure or continue your stay

This morning check out from your hotel in Cortona and return your car at the car rental depot. You can decide to end your tour here or continue with another of our self drive itineraries or add some nights in Rome or in another city.