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Often when people begin planning their trip to Italy they only think of the main attractions, Rome,Florence,Pisa,Naples,Venice and while these are sunning places to visit rich with history and elegant Italian architecture. Outside the giant lines to the Sistine chapel in Rome and the hoards of countless tourists posing  with their hands pretending to be holding up the leaning tower of Pisa there is another more quiet and naturally beautiful side of Italy just waiting to be explored.


Image credit: siepert

What if next time you flew into Italy instead of being confined to standard tourist routes on bus’s and trains, only being able to stop at the places they let you, You could the have the freedom to go off the beaten track and travel the roads less traveled by renting your very own car and going on your very own Italian road trip.


Image Credit: Giovanni Maw

So grab your keys, buckle up your seat belt as we head off on a road trip adventure exploring all the beautiful off the beaten track hill town’s of Tuscany.



First town on the list while not really off the beaten track with over 163,000 international arrivals yearly, but a great place  to start your Tuscan road trip is the Beautiful hill-top town of Siena, Famous for its fabulous Italian cuisine, Museums, stunning main square and the home of the Palio horse race.

Siena shot


Next on the list with a quick 48 minute drive from Sienna is the fortress topped town of Montalcino, renowned for it’s fine production of wine, with “The Brunello” being one of the most popular. If the breathtaking views of the surrounding vineyards, olive groves and and beautiful Tuscan hills is not enough then the impressive castle and fortress looming over the city is bound to have you in awe.


Image Credit: Nadia Fondelli


Located between the town’s of Montalcino and Montepulciano just a short 25 minute drive is the  small renaissance style town of Pienza, With the main attraction of the town being the The Duomo cathedral located in the main Piazza and the surrounding Tuscan hills this small gem of a town is definitely worth a visit.


Image Credit: Moedermens


Located to the east of Pienza lies  one of the most architecturally beautiful medieval towns in Tuscany, Montepulciano. Renowned for it’s delicious Cheese, Pork,,”pici” pasta, lentils, and honey. But what it’s internationally famous for is it’s Vino Nobile wine which is rated as one of Italy’s best. So grab yourself some mouth watering food and some amazing wine and head to the top of the beautiful Palazzo del Commune located in the Piazza Grande, with stunning panoramic views of valley.

Tuscany_town_ Montepulciano

Image credit: Lo.tangelin

San Gimignano

Last on the list located to the north of Siena just 45 minute drive away is the town of San Gimignano, renown for its medieval architecture and over 15 preserved  medieval towers, giving the town it’s name “Town of Fine Towers“. With breathtaking views from the tower tops over the town’s iconic skyline to walks through the cities narrow medieval alleyways this town is definitely not one to miss.

Tuscany_town_ San Gimignano_streets

Image Credit: 7Bart

So there you have a list on just a handful of the many beautiful towns in Italy’s Tuscan countryside,However with so many amazing and varied landscapes across all of  Italy there are so many area’s to explore, If your looking for something a bit more rugged than the rolling warm hills of Tuscany then try going on an Italian Alps Road Trip through the icy hills of Italy.

What is your favorite region of Italy to road trip in?

2017-08-29T01:42:34+00:00 2 Comments


  1. Murissa March 5, 2014 at 5:22 pm - Reply

    San Gimignano was one of my favourite day trips from Florence.
    Exploring the northern Veneto region is also a great place to see unexpected Italy. There are so many small towns that hold impressive gems of art history and architecture.
    Great pics!
    Murissa recently posted..Murder & Pigs Feet: The English Market in Cork, IrelandMy Profile

  2. Hitch-Hikers Handbook October 26, 2014 at 10:09 pm - Reply

    Great post! We went to Siena last year and loved it! (well, the architecture, not so much the prices!)
    Hitch-Hikers Handbook recently posted..Travel Photography Competition – week 110My Profile

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