• 29 December 2020

A trip to Tuscany is characterised by rolling hills, vineyards and dozens of hilltop towns – everything you need for a quintessential Italian experience! If you want to slow down and drink in the Italian culture there is no better place to do so than in the historic towns dotting the countryside.

Slow down and experience these beautiful hill towns on your next foray to beautiful Italy:

San Gimignano

San Gimignano is a place of palpable history, charming rural landscapes and beautifully preserved medieval cityscapes. Fourteen stoic towers reach into the sky to create a majestic skyline amidst the surrounding Tuscan hills. San Gimignano was originally an Etruscan village named for the bishop of Modena who is credited as saving the settlement from Attila the Hun. In the 1100s the town flourished due to its location on the Via Francigena and it became fashionable for minor nobles to flaunt their wealth by building a tower that surpassed that of their neighbours, which accounts for the impressive structures that remain today. Outside of these impressive medieval skyscrapers, there are also two well-known palaces here: Palazzo Nuovo del Podesta and Palazzo de Popolo, a medieval criminal and torture museum. If you like souvenir shopping, San Gimignano is one of the best spots to find some of the best and most beautiful handcrafted Italian pottery and ceramics.

View of San Gimignano Italy
San Gimignano showcases an impressive skyline.


Pisa might be best known for its most unfortunate architectural and historic project, the Leaning Tower of Pisa, but there is more to this Tuscan hilltown that meets the eye. This maritime powerhouse is now a spellbinding city with a vibrant student culture, which spills over into the town’s cuisine and entertainment. Throw in a few Gothic churches and well-maintained Renaissance piazzas filled with colourful locals, and you can see why it is such a popular destination with visitors from around the world.

View of Pisa in Italy
There is more to Pisa than the famous tower!


Siena’s compelling architecture is a visual feast will have you riveted. The entire city is basically one big al fresco museum dedicated to Gothic art that lives in perfect harmony with the medieval monuments and modern structures that line its streets. The city square, Piazza del Campo, is also regarded to be one of the most famous and most beautiful piazzas in Italy and the place where the famous Palio horse races take place twice a year. Wander around, take a seat at an enoteca or deli for an aperitif and gaze in wonderment as you are transported to the 15th century when living was slow and easy. It’s one of the most famous Italian cities for a reason.

View of town of Siena in Italy
Beautiful Siena plays host to the Palio Horse Race twice a year.


Situated in the Valdinievole area, Montecatini Terme is world-renowned for its thermal spas and Italy’s foremost spa town. Here you can bathe in spring-fed stone pools and sulphurous hot springs that burst forth from the ground, indulge in spa treatments or simply spend the day soaking along with the locals – the choice is yours. Alternatively, take a walking tour of the town’s historical fountains or visit the Viale Verdi to view the summer residence of the famous Medici family.

View of Montecatini town in Italy
Montecatini is a beautiful spa town in Tuscany.


Perched precariously on a narrow ridge of volcanic rock, the town of Montepulciano is not to be traversed by the faint of heart – it is steep as steep can be! That said, if your calf muscles are up to the task, you’ll be able to drink in the singular architecture and ambience of a city that straddled the political divide between Florence and Siena for so long that it developed a wholly unique culture in the process. Here Gothic strongholds rub shoulders with Renaissance mansions and ice-cold Vino Nobile awaits at trattorias that overlook the majestic Val di Chiana. In one word: magic!

View of Tuscany landscapes from town of Montepulciano Italy
Enjoy the views of the Tuscan landscape from Montepulciano.

There a number of gorgeous Italian destinations just waiting to be explored! Make your Italian dreams a reality with a tour through Italy. See Rome, Florence, Venice, the Italian Riviera and more!

Questions & Comments

  1. Shannon Angell says:

    I would like more information action on pricing for this trip

    • Expat Explore says:

      Hi Shannon,

      Thank you for your comment.

      I have sent you an email. We can communicate further from there.

      Wishing you a Happy, Blessed, Prosperous and Healthy 2021

Join the Expat Explore family!

We’ll deliver top travel tips, insider info and travel inspiration right to your inbox.

By submitting this form you agree to our Privacy Policy.

Secured by thawte

256 bit SSL encrypted security

Mastercard Visa