A Taste of Tuscany Driving Holiday - 5 Days

Tuscany Driving Holiday in Italy

Our Taste of Tuscany driving break takes you on a journey of discovery through the most beautiful regions of Tuscany, sampling gourmet highlights along the way, visiting medieval hilltop towns, and driving the most scenic driving routes. 

This 4-night trip starts in the historic city of Florence and includes 3 full days touring on the best roads in Tuscany.  The first tour takes you around the wine regions of Chianti, with time to stop for a pasta cooking mater class in the heart of Chianti.  The second tour takes you south on a loop across the spectacular Tuscan vistas of the Crete, or Val d'Orcia, with its sweeping Cyprus tree-lined roads, are the driving image most commonly captured around the world.  The final tour takes in drives around the hilltop fortified towns that make up the "borderlands of Florence" including San Gimignano, Certaldo, and Monteriggioni.  Italy never fails to embrace you, and this Tuscany trip really combines the best driving routes, fantastic cultural sights, to create a truly rounded driving trip.

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A Taste of Tuscany Driving Tour

Day 1 - Arrival Florence - Transfers to your hotel

Arrive at Florence airport and make a quick 15min transfer by taxi to your hotel for the first night, the Palazzo Castri. This updated boutique hotel with spa is just moments from city center, and provides tasteful luxury and privacy with just the right amount of Italian flare.

**OPTIONALLY, upgrade to the 5 Star Superior Villa Cora for nights 1 and 4. This is a 19th-century building surrounded by a park in the quiet Borgo San Frediano district. The hotel offers a truly luxurious welcome to Italy, with its private spa and pool, Michelin Star kitchen and delightful, individually styled bedrooms. It is the perfect place to start your adventure if you want extra special lodging that is a cut above the rest. This 2 night upgrade would add 400 euros per person.

Views across Florence from Piazzale Michelangelo

After checking into the hotel, take a stroll to the old town of Florence, which is less than 5 minutes away, then later, just chill in the hotel's wonderful gardens, a small oasis in the heart of the city

Overnight Hotel: 4* Superior Palazzo Castri 1874 Room type: Deluxe Double

Day 2 - Tour of Chianti Country

In the morning you will be met at the Villa by your Ultimate Drives Drive Concierge, who will provide you with a full briefing and walkthrough of your itinerary, the car handover will take place and you will be on your way.

Car Handover at the Villa Cora Hotel 

Your first tour will then start with a run south from Florence via the super scenic SR222 - famous as part of the legendary Mille Miglia road race route.  The road will take you directly into the rolling hills and vineyards of the Chianti region, dotted with wineries and olive groves, one of the most beautiful landscapes you can find in the whole of Italy.  The drive will then make a loop of the most beautiful hilltop towns in the region, including Greve, Castellina, and Radda in Chianti, with optional stops by at the Viticcio winery estate and the Casa del Chianti Classico for a tasting.

Lunch and Olive Oil tasting at Badia Coltbuono

Next, head slightly east and across to the beautiful Monastery / Olive oil facility at Badia Coltbuono - here you will stop for lunch, then an olive oil tasting at the old monastery.  After lunch, continue your loop around the region, heading further south, where you can stop up and explore the grounds of Castel di Brolio, and also stop by the wine shop of Vineyard Felsina for a final stock up, before heading to your hotel for the evening - the 5 Star Le Fontenella, set in the heart of Chianti country, amongst its own vineyards, with wonderful views across the rolling hills of Chianti. 

Dinner at Hotel Le Fontanelle 

Overnight Hotel: 5* Superior Hotel Le Fontanelle, Chianti Country Room type: Classic Double

Day 3 - Le Crete and Val d'Orcia

For your second tour, you will head south to the beautiful Val D'orcia / La Crete region, famous for its rolling hills, unique vistas, and Cyprus tree-lined roads, for some people this really is the iconic Tuscan landscape.  This is also the region of Tuscany with some of the best thermal waters and spas.  The tour will of course take in the beautiful hill-top village of Montepulciano, making wines by the same name, before stopping by at the spa town of Bagno Vignoni

Arrivals at the Hotel Le Fontanelle 

Continue south, and you will stop by at a wonderful farmhouse where a master class in pasta making has been arranged, where you can prepare and cook your own pasta, the enjoy it with a glass of the local wines and some incredible hand made local sauces. 

Pasta Cooking Classes in Val d'Orcia

After lunch, explore the vineyards of the Brunello region, there are several great vineyards highlighted on the drive, including Poggio di Sotto.  Loopback north, through Val d'Oricia, making an optional stop at Abbazia di Monte Oliveto Maggiore, before continuing back to Chianti country for a second evening. 

Overnight Hotel: 5* Superior Hotel Le Fontanelle Room type: Classic Double

Day 4 - Borderlands of Florence & Route Mille Miglia

Today you will tour through the rolling Tuscan hills west of Florence, visiting some of the most beautiful and well-preserved towns in the region, including the hilltop towns of Monteriggioni, Certaldo, and San Gimignano. This tour is very much about a combination of sightseeing and drives. After heading through the beautiful hilltop village of Certaldo, you then drive to the gem of the region, San Gimignano.

Views to Hotel Le Fontanelle through its own vineyards

It’s also the only city in the region that has managed to conserve fourteen towers of varying height which have become its international symbol. After lunch, spend some time exploring on foot, shop for the best local produce and wines from the region. The final drive back takes you along the SP 222 (Strada Chiantigiana) arguably the most scenic route in central Tuscany, as it cuts its way north through Chianti Country.

The scenic SR222, part of the Mille Miglia route

A final stop of the day is made in the village of Greve in Chianti, for an afternoon coffee and cakes, before completing the drive back to Florence for a final evening.

Overnight Hotel: 4* Superior Palazzo Castri 1874 Room type: Deluxe Double

Day 5 - Morning at leisure in Florence

On your final day, spend some more time enjoying the delightful city of Florence - the hotel will be delighted to take care of your luggage whilst you spend a day in the city, then later shuttle back to the hotel, and continue your onward journey plans. 

To ask us a question about our 'A Taste of Tuscany Driving Holiday - 5 Days' Driving Holiday, please fill out this simple form below. One of our experienced staff members will be in touch within 24 hours.

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