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At Tuscany the journey makes the destination — and the scenic roads over soft rolling hills connecting countless medieval towns make it the perfect region to drive. But it is easy to get lost in this beauty and miss the best parts. To help you avoid this we have summarised the four most scenic drives of Tuscany.

Please check out our luxury Tuscany Driving Tour to enjoy effortless navigation with a pre-programmed GPS.

ROUTE 1 — UNESCO protected Val d’Orcia in Tuscany

The stunningly gorgeous valley with endless views over the idyllic Tuscan landscape and the most iconic cypress three lined roads we all know from pictures. We recommend accommodation for at least two nights near Siena. The town itself is absolute worth a trip, but we recommend staying in the countryside to experience Tuscany with all senses. Form a loop to explore the Val d’Orcia valley in one day and have the second day to relax at your hotel. The charm of Tuscany deserves time to sink in and leave unforgettable travel memories. We would suggest the following loop: 


San Quirico D’Orcia — Pienza — Montepulciano — arguably the most iconic towns of Tuscany.


The number one of all scenic roads in Tuscany is well known for its S-shape and has graced countless postcards - between La Foce to Radifocani in Tuscany you will find what you’re looking for. Also please don't miss out on the Vitaleta Chapel, a small church flanked by cypresses crowing the hill. This must be the most photographed spots in all of Tuscany.

ROUTE 2 — The enchanting “Via Chiantigiana” (Chianti Wine Road) 


This route passes through some of the most charming towns in Chianti and has those picture perfect vineyard landscapes and silvery olive groves you've been looking for. Since the 18th century this region is well known for its wine production.The "Via Chiantiagiana" is connecting the major Tuscan towns of Siena in the south and Florence in the north.

The SR222 is also part of the historical Mille Miglia route — the famous "thousand miles" event is a popular open road race in Italy, which had originally taken place 24 times, from 1927 till 1957. Mille Miglia played a role in making car manufacturers like  Porsche, Maserati, Ferrari and Alfa Romeo world-famous. 

We recommend planning in an entire day to have time to stop for the many olive oil manufacturers and wineries along the road. Stick to the wonderful olive oils when tasting a sample.  A bottle of that prestigious and world famous Chianti Classico DOCG wine should be kept until the evening at your hotel. Follow the curvy road weaving its way through many ancient villages and towns. We recommend the following routing: 


Greve — Panzano — Castellina — Gaiole

ROUTE 3 — The Hilltop Town Route


This route is made of the stony villages dotting the Tuscan hills southwest of Florence. Oh which San Ginmignano — with its 14 medieval towers is probably the most famous. The towers form a medieval skyline that don't fail to impress until today. Back in the day it has been an ongoing challenge among the rich of the town who has the most impressive tower to demonstrate their wealth and power.


Only an hour drive from there you will find another hilltop town:  Volterra with the most famous Roman ruins in the center of the city.


You can comfortably visit both hill top towns in one day or choose one for your itinerary before you continue further south to Abazzia di San Galgano — also called: the abbey without a roof. The magical photo stop is a nice stop before you reach the world famous cathedral of Siena.

ROUTE 4 — the Futa & Raticosa Mountain Passes


Connecting the towns of Bologna in the Emilia-Romagna region with Florence in Tuscany is our Futa & Raicosa Pass Route.  Both passes sweep along the Italian SP65 Road across the Apennines Mountains and are known to be more or less official testing grounds for new Ducati motorbikes produced near Bologna.

The two passes are also the only real stretches of the Mille Miglia race that are still drivable as they were in 1955. Also in 2019 the MM race was running over the Futa and Raticosa passes. Hundreds of Ferrari’s, vintage cars and other supercar brands chased down the seemingly endless sequence of fast sweepers, tight hairpins, chicanes, undulations, short and sharp sections.

The region is also a place, which breathes history. During the WWII the last German defense line, called: “Gothic Line” was located in the area. On 21 April 1945, after heavy fights, the Allies managed to break trough. On top of the Futa Pass on 903 meters above sea level is today the German war cemetery (the largest war cemetery in Italy), with 30,653 graves.

While in the area we recommend visiting the motor valley near Bologna. Lamborghini, Ferrari, Maserati and Pagani have very interesting museums surrounding the town of Modena. Motorbike lovers might want to visit the Ducati Museum.


 When to travel to Tuscany?


Tuscany is worth a trip the entire year – green during spring and kind of sunburned yellow during the hotter summer month.


Tuscany always delivers a different experience with each season. Start your drives early so you get to enjoy the pool at your hotel during the afternoon and to avoid the heat and crowds during the high season in July/August.


The best time of the year to visit Tuscany is September – October, just in time to witness the harvest of the grapes.

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