Tuscany & Florence Driving Tour - 5 Days

Our Florence and Tuscany driving break in tuscany break takes you on a journey through the most beautiful regions of Tuscany, sampling gourmet highlights along the way, visiting medeival 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, the second tour across the spectacular Tuscan vistas of the Crete  - the best driving roads in Tuscany, and the final tour takes in drives around the hilltop fortified towns that make up the "borderlands of Florence" including San Gimigiano, Certaldo and Monteriggioni.  You will spend the first and last evening at the beautiful 5 Star Villa Cora, a short hop from the center of Florence, yet quiet and tranquil in the Villa district south of the city, with the middles evenings in the heart of Chianti Wine region at the 4 Star Superior Borgo Scorpeto resort. 

Italy never fails to embrace you, and this Tuscany trip really combines the best driving routes, fantastic cultural sights, to created a truly rounded driving trip

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Day 1 - Arrival Florence - Transfers to the hotel

Arrive at Florence airport and transfer to your hotel for the first night. Villa Cora, is a 19th-century building surrounded by a park in the trendy Borgo San Frediano district, 10mins stroll from the center.

The rooms at the hotel are decorated in modern style and it is well located, just a 15min walk, across the River Anro and into the center of Florence.

Overnight Hotel: 5* Superior Villa Cora Room type: Classic Double

Day 2 - 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 hand over will take place and you will be on your way.

Your first tour will take you south from Florence and into the rolling hills and vineyards of the Chianti region. Your will make a tour 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 tastings.

After, head to the beautiful Monestary / Oilve oil facility at Badia Coltbuono, for lunch and oil tasting.  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

Now looping back north to your hotel for the evening, in the heart of Chianti country.  Wine tastings can be arranged at the hotel that evening. 

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

Day 3 - The Crete to Val d'Orcia

For your second tour, you will head south to the beautiful Val D'orcia / La Crete region, famous for it's 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 for lunch.

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

Overnight Hotel: 5* Superior Hotel Le Fontanelle Room type: Superior room

Day 4 - Tour the 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 Montiriggioni, Cetaldo and San Gimigiano. This tour is very much about a combination of sightseeing and the drives. After heading through the beautiful hilltop village of Certaldo, you then drive to the gem of the region, San Gimigiano.

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 by 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.

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: 5* Superior Villa Cora Room type: Classic Double

Day 5 - Visit Florence, then later return to Florence Airport

On your final day, spend some more time in the city of Florence, or relax in the hotels grounds.

To ask us a question about our 'Tuscany & Florence Driving Tour - 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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