If you travel to Tuscany for the fine arts at Florence and Siena, the excellent Italian food and wine or the beach. No trip is complete without the rolling hills and extraordinary countryside Tuscany has to offer.


It's safe to say that in Tuscany the journey makes the destination — the scenic roads reaching over soft rolling hills to connect the countless romantic medieval towns make it the perfect region for a driving tour. Almost a crime for tourists to travel on a direct route between two points.


But getting lost in all this beauty and perhaps missing out on the best parts is not what we want to happen. To help you avoid leaving Tuscany not as a fan we have summarised the four most scenic drives in Tuscany below.




Tuscany is a true gem and full of beautiful roads and scenic drives. The best one can be found in the Val d’Orcia valley.


This is 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 minimum two nights near Siena. 



The town with the impressive Siena cathedral itself is absolute worth a trip, but we recommend staying in the countryside to experience Tuscany with all senses.



From here you can form a loop to explore the wonderful Val d’Orcia valley in a single day and have the second day to relax at your hotel. The charm of Tuscany deserves some extra time to allow the unforgettable travel memories to sink in. We are suggesting the following loop: 



 — arguably the most iconic towns of Tuscany.


The number one of all scenic roads in Tuscany has graced countless postcards. Between La Foce to Radifocani in Tuscany you will find the S-shape road lined by an army of cypress tress.


Don't miss out on the Vitaleta Chapel closy by, also flanked by cypresses. This two locations must be the most photographed spots in all of Tuscany.







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 scenic 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.

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 between 1927 and 1957. Mille Miglia played a major role in making car manufacturers like  Porsche, Maserati, Ferrari and Alfa Romeo world-famous. 

We recommend planning in an entire day to have dedicated to the Chianti Wine Road.



Plan enough time to stop for the many olive oil manufacturers and wineries along the road. Stick to the wonderful olive oils when tasting a sample and keep a bottle of that prestigious and world famous Chianti Classico DOCG wine for later. Follow the curvy road weaving its way through many ancient villages and towns.



We recommend the following routing: 





This route is made of the stony villages dotting the Tuscan hills southwest of Florence.



Of 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 away is  Volterra with the most famous Roman ruins in the very centre of the city.


You can comfortably visit both hill top towns in one day 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.

Most towns in Tuscany have a car park close by. The bigger ones even offer a shuttle service during the high season. You will find many beautifully decorated shops and restaurants serving local food.


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 defence 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.




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


Tuscany 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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