8 Days Self Drive Umbria and Tuscany Tour departing from Rome

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Escorted Tours
difficulty Very easy
Wheelchair Not Accessible

8 Days Self Drive Umbria and Tuscany Tour departing from Rome

An amazing 8 Days Tour to discover Tuscany and Umbria. You will get the chance to admire the architectural beauties of those regions, together with their food and wine specialties!

Get a taste of "Dolce Vita" in Rome
Find your inner chef during our cooking class in Florence
Drive through Chianti hills and taste the wines produced here
Learn "cashmere” production techniques
Let Siena, Assisi and Firenze enchant you with their beauties

Day 1 – Rome

Arrive at Leonardo da Vinci International Airport and reach your hotel located in the city center. Check in and spend the day at leisure in the Eternal City in the spirit of ‘La Dolce Vita’ (meaning “The Good Life”). Spend the night in Rome.

Day 2 – Rome, Florence

Depart to Florence after breakfast. Check into your hotel and start a walking tour around the core of Italian Renaissance. Enrol in an enriching cooking class in the historical city center followed by a light dinner. Overnight stay in Florence.

Day 3 – Florence, Chianti Area 

Make your way to Tuscany after breakfast. Dedicate the day to enjoy the marvellous Chianti hills, situated along the Via Chiantigena (an ancient road connecting Siena with Florence and stretching over the hills of Chianti). Meet the winemakers of the Biodistretto (Bio district) at Tenuta Fontodi in Panzano for a tour of the cellars and tasting session. Head over to Greve in Chianti and sample some delicious salami at Antica Macelleria Falorni. After which, we will enjoy some organic cheeses (including baby goats cheese and fresh ricotta) at Podere Le Fornaci, where they manufacture these cheeses from the milk of the goats that graze in the Chianti hills. In the afternoon, we will learn about cashmere making, from its origins to the end product of hand weaved accessories at a small bucolic farm. Head back to Greve and spent the rest of the day at leisure. Indulge in a delectable dinner at Trattoria Mangiando before returning to your hotel in Chianti for an overnight stay.

Day 4 – Siena and San Gimignano

In the morning, depart to Siena, a city with one of the most distinguished medieval architectures in all of Italy. Stroll through the alleyways of this enchanting city, marvelling at its gothic architecture and art-filled piazzas.
Check out the famous site of Siena’s horse race, the Palio at The Piazza del Campo. Drop by the many famous patisseries and try out delectable traditional sweets such as the Panforte. Shop at leisure. Along the way to San Gimignano and passing by the ancient Via Francigena, grab lunch prepared by some of the traditional local produce such as the Certaldo onion (Slow Food Presidium), and the organic extra virgin olive oil from San Gimignano at the cozy farmhouse Il Castagnolino. Be enlightened by the professionals here on the process of manufacturing organic olive oil. In the afternoon, we will join a guided visit of San Gimignano, one of the most intact medieval villages in Italy.
Keep your eyes peeled at the many imposing ‘skyscrapers’ of the 13th and 14th centuries. Wander through the narrow and characteristic streets leading up to the top of the village for breath-taking views of the city’s surroundings. Pop by one of the many quaint cafes in the area and sample excellent local Vernaccia wine. Return to the hotel and retire for the night.

Day 5 – Orvieto, Pian di Porto

After breakfast, join a guided tour to Orvieto, perched on the top of a rock and offers stunning panoramic views. During the tour, we will be visiting many of Orvieto’s historic jewels, such as the Duomo, a Gothic cathedral. Head over to Palazzo del Gusto, the main office of the Enoteca Regionale of Umbria where we will indulge in a light lunch including a tasting session of Umbrian wines accompanied by local produce. Before departing, you might embark on a quick visit to the Adriano pastry shop to sample Orvieto’s traditional cakes and sweets, such as chocolates made with chillies and saffron. In the afternoon, we recommend dropping by Todi, another captivating medieval village and spend the day at leisure strolling around its ancient monuments and craft shops. Return to the hotel and spend the night in Umbria countryside.

Day 6 – Assisi, Bevagna, Montefalco

Embark on a guided tour of Assisi and the Basilica of St. Francis. After which, drop by Bevagna, a charming and ancient medieval village before heading off to Montefalco, yet another magical town perched on a hilltop with beautiful views of its surrounding verdant hills. Discover the charms of the city and sample the famous Sagrantino wine at the Azienda Scacciadiavoli. In the afternoon, we will visit a farm filled with 3000 ancient olive groves belonging to the Azienda Romanelli family. Here, we will learn about the many plant varieties and the sophisticated production techniques for extra virgin olive oil, along with a tasting session. Overnight stay in Umbria countryside.

Day 7 – Florence

After breakfast, we will head back to Florence. Check into your hotel and spend the rest of the day at leisure. We highly recommend taking a relaxing stroll around its historical center. For lunch, indulge at one of the restaurants in the historical centre.
Return to the hotel for an overnight stay.

Day 8 – Departure

After breakfast, checkout and take your private transfer to Florence airport for your return flight.

  • Rome
  • Florence 
  • Chianti
  • Siena
  • San Gimignano
  • Orvieto
  • Pian di Porto
  • Assisi
  • Bevagna
  • Montefalco
  • Departure
  • 7 nights in 4* hotels
  • Breakfast
  • Dinners and lunches as per perogram
  • Visits with private guides in (no entries included):HD Florence walking tour (3 hours)HD Siena walking tour (3 hours)HD San Gimignano walking tour (3 hours)HD Orvieto walking tour (2 hours)HD Assisi walking tour (3 hours)
  • Tastings as per program
  • Cooking lesson and light lunch in Florence
  • Visit at a Chianti farm
  • Private transfer from Hotel to Airport in Florence
  • Trasport
  • Tips (optional)
  • Entrance tickets
  • City taxes
Meeting point: 

Confirmation will be received within 48 hours of booking, subject to availability. Once your booking is confirmed we will email you a voucher. This is your ticket and proof of purchase.


We suggest wearing comfortable clothes and shoes.
Please note that transport is not included in this tour. If you need to rent a car, contact us for a custom quotation.
Kids under 2 years old travel for free.

Confirmation will be received within 48 hours of booking, subject to availability. Once your booking is confirmed we will email you a voucher. This is your ticket and proof of purchase.