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Towns and Villages in Tuscany

There are some truly spectacular towns and villages in Tuscany. From medieval hilltop villages, to larger towns with beautiful old town centres. Or if you prefer something a little more upbeat, there are several big cities packed with culture and entertainment. Each region in Tuscany has something unique to offer. Wander through the cobbled streets of quaint Italian towns and you will soon fall under the spell of Tuscany.

Some towns overlook rolling hills, endless fields with rows of vineyards and rustic castles can be spotted on the horizon. Sit and watch the world go by in a local Italian cafe, browse through quirky gift shops or admire the striking buildings that reside within the city walls.

Our private pool villas, hamlets and farmhouses are located within close proximity to Tuscany’s most impressive towns and cities.

Where to visit

We have all the information you need about all the regions and key places you should visit on your holiday to Tuscany, including the 3 main cities Florence, Siena and Pisa.

Northern Tuscany

The scenery throughout Tuscany varies quite considerably depending on where you go. The landscape and terrain in the North is very different from the South. Its unspoiled landscape is mountainous, more rugged and broken up with thick woodland.

Just like the South, it has traditional hilltop villages and medieval castles, but here the pace is much slower, despite the area being densely populated. As well as being by the breathtaking Apuan Alps, from most locations in Northern Tuscany you can easily reach the coast within a 30 minute drive.

Northern Tuscany offers the best of both worlds, soak up the sun on the beach, go hiking in the mountains, or visit amazing cities and towns such as Florence, Lucca, Pisa and Pistoia. Northern Tuscany may be less stereotypically Tuscan but it has classic architecture, artistic treasures, striking hilly landscapes and plenty of cultural events to enjoy.

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Central Tuscany

Can’t decide where to stay in Central Tuscany? Browse through some of the places below for further inspiration.

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Southern Tuscany

It’s easy to see why Southern Tuscany is such a popular area to visit, browse through the towns below to find out more.

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Umbria holidays

Umbria is often viewed as Tuscany’s sister, in many ways it mimics Tuscany’s delights, but also has its own distinct character. Umbria, known as ‘the green heart of Italy’ sits right in the middle of the country.

It’s about half the size of Tuscany, which means most of the region can easily be explored. Umbria is serene, understated, breathtakingly beautiful, and most importantly, unspoiled. It has long lived in the shadow of Tuscany, but visitors are discovering its charms and learning that a holiday in Umbria is not to be missed.

The landscape is littered with rolling hills, streams, valleys, olive groves and woodland. Visitors report there being a special quality of light that illuminates the horizon. Umbria is also famous for being the birthplace of the saints, which further contributes to its magical appeal.

This region is known for its olive oil, truffles, fine cured meat and full bodied wine. There are plenty of gorgeous hill towns to visit such as Assisi, Orvieto and Perugia, as well as quaint villages like Trevi, Spello and Montefalco. What are you waiting for? View the links below and book a holiday to Umbria.

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Val d'Orcia

The Val d’Orcia is a ravishing rural area running into le Crete Senesi, but within sight of hulking Monte Amiata. For many, this is the loveliest area in Tuscany, with Unesco-listed countryside, perfect hilltop villages, remote abbeys and evocative castles. Foodies, walkers and spa-lovers will take to the thermal spas, rustic inns, myriad wine trails and meditative walks. The Val d’Orcia represents quintessential Tuscany, with clusters of cypresses, ribbons of plane trees, vineyards on the slopes, and farms perched on limestone ridges. But it was not this alone that won the area Unesco World Heritage status – it’s also about the harmony between the Tuscans and their landscape, shaped by their mellow way of life. Once depopulated, these medieval villages are now enjoying a belated renaissance. San Quirico d’Orcia may be the gateway to the area but MontalcinoPienza and Montepulciano also make delightful stepping-stones to scenery landscaped since time immemorial.

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Experience an official tuscany tour with

Rent a Car for Wedding: Black Mercedes E Class

During the most amazing day of your life, rent the perfect car and surprise all your Guests and your partner!

from 754,58 US Dollar

Florence Cooking Class: Learn How to Make Gelato and Pizza

Combine your love of pizza and gelato (an Italian version of ice cream) with a unique cooking class in beautiful Florence. Learn how to make gelato and cook an authentic Italian pizza with a professional chef who will guide and teach you along the way. Discover and taste the many Italian gelato flavors that are made in Italy, and sample an array of Italian pizzas. Your new cooking skills will be the best souvenir you take home from your trip to Italy.

Numbers are limited to 25 people on this small-group tour, ensuring you'll receive personalized attention from your knowledgeable guide.

from 65,36 US Dollar

Local market visit and dining experience at a Cesarina's home in Siena

Visit the vibrant local market and the traditional food shops with the Cesarina and immerse yourself in a private dining experience at the Cesarina's home. Enjoy an exclusive show cooking and  taste authentic Sienese recipes treasured in family cookbooks passed down by real Italian Mammas. Feel the warmth of Italian hospitality as you connect with local people.

Enjoy a 4 course-menu including starter, pasta, main course with side dish, dessert with  drinks included (water, selection of red and white wines from Tuscany cellars and coffee). At the end of the experience, take your souvenir back home: the official Cesarine apron and shopping bag.

from 172,3 US Dollar

Brunello & Rosso di Montalcino Grand Wine Tour in Vald'Orcia Region (Tuscany)

Brunello di Montalcino is one of the best wines in the world, destined for long ageing, making it better and more complete over time. According to the regulations, Brunello must age for a minimum of 5 years although it is customary to lay it down for 10 years. It can remain in the cellar for 30 years while some of the very exceptional vintages last for 100 years or more, as the Brunello produced by Biondi Santi.

Brunello di Montalcino is made with only Sangiovese grapes cultivated exclusively in Montalcino, a small Tuscan town that is forever linked to its wine, to that certain clone of Sangiovese Grosso that. 

from 118,83 US Dollar
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