Amazing Towns of Tuscany

By Sue Lobo
Picturesque rolling hills, towns filled with art and architectural treasures and a renowned food and wine culture; Tuscany is the heart of La Dolce Vita – the sweet life – and the area most associated with superb food and wine.

So what towns in Tuscany should you visit?  All of them if you have the time!

We’re sharing out list of the most Amazing Towns of Tuscany.

Amazing Towns of Tuscany


Siena is Italy’s loveliest medieval city. Siena’s heart is its central piazza known as IL Campo (pictured below,) famous for the “Palio”, a horse race run around the piazza two times every summer.Siena is said to be founded by Senio and Ascanio, sons of Remus,of the famous dou Romulus and Remus who founded Rome. Statues of the wolf feeding the twins can be found throughout Siena. The city sits over three hills with its heart the huge piazza del campo, where the Roman Forum used to be. It is the setting for the Palazzo Publico (Town Hall) and one of the tallest towers built in medieval Italy, the Torre del Mangia. Some of the many attractions to visit in Siena are, Piazza del campo, Palio of Siena, Piazza del Duomo, Basilicia of San Francesco, House of St. Catherine, Church of Santa Maria di Provenzano, Church of St. Christopher, Basilica of Sna Domenico, Fountains of Fonte branda, Loggia della Mercanzia, Piazza Salimmberi, Piccolomini Palace and the list goes on and on.

Piazza del Campo in Siena Italy

Pienza and Val D’Orcia

Pienza is a tiny village in Southern Tuscany in the valley of Val d”Orcia. Pienza stands high atop a hill with extraordinary views. This charming village is known as the “ideal city of the Renaissance”. Piazza Pio II and Duomo or Cattedrale deli’ Assunta are not to be missed. The imposing Palazzo Piccolomini has a delightful Loggia with hanging garden with breathtaking panoramas of the Val d”Orca Valley.Some of the scenes from Romeo and Juliet were filmed here. Pienza is also the city of cacio, which means cheese. The Pecorino of Pienza is a tasty cheese made from sheeps milk. The town streets are full of small charming shops and fantastic restaurants.

Town of Pienza with the typical Tuscan hills

San Gimignano

Welcome to San Gimignano, Italy – An Italian and European Paradise. — It’s no wonder Italy is one of top destinations in Europe.  San Gimignano, Italy is a wonderful destination for even the most discriminating traveler. Come explore San Gimignano.

It’s no wonder San Gimignano, Italy is one of top destinations in Europe. It offers a traveler a feast of opportunities to fall in love with this charming country. There’s no escaping it San Gimignano, Italy means history, ruins, food, art and love…There’s layers of the stuff! Activities usually involve nothing more strenuous than eating, drinking and listening to good music. Find a cafe at twilight and watch the shades of pink turn to gold and copper before night finally falls. After dinner you can stroll by the fountains and have a gelato or an espresso, and pause in the early evening to experience the charm of San Gimignano, Italy as evening comes.

Medieval town of San Gimignano, Tuscany, Italy


Pitigliano is built on a promontory surrounded by bright green valleys grooved by the Lente and Meleta rivers. The high cliffs are chiselled with thousands of caves and tower-houses. The town takes pride in its heritage; the prehistoric period with its tombs discovered along the city wall and surrounding area.. Another key to appreciation of Pitigliano is the famous Jewish ghetto. This town has been called “Little Jerusalem” because of its large and active Jewish population which settled there in the 15th century. Visit the Sinagogue and the Jewish Cemetary with the unleavened bread oven, the cellar carved into the rock where Kosher wine is produced, the Kosher butcher, the cleaning baths for womed and the cleaners; all open to the public.



Volterra is built on a high plateau enclosed by volcanic hills midway between Siena and the sea. This magic and mysterious city has its roots in three thousand years of history. The ancient city walls, the imposing Porta al’Arco, the necropolis of Marmini and the numerous archeological finds are conserved in the Museo Etrusco Guarnacci. Visit the theatre of Vallebona from the period of Augustus. Today the city conserves the Medieval aspect of the 12th century city walls and the urban layout with narrow streets, palaces, tower houses and churches.

View of medieval city of Volterra


Montepulciano is a medieval and Renaissance hill town and commune in the Italian Province of Siena. It sits high on a 605-metre limestone ridge. Montepulciano is a major producer of food and drink. Renowned for its pork, cheese, pasta, lentils and honey, it is known world-wide for its wine.The main street of Montepulciano stretches from the Porta al Prato to the Piazza Grande at the top of the hill. The city is renowned for its walkable, car-fre nature. In the Piazza Grande, there are several stalls for winetasting from the local vineyards. The Cantina Contucci is off the Piazza Grande, where you can view how the city jail was converted into a wine cellar.



Cortona is a town and commune in the province of Arezzo. It is the main cultural and artistic center of the Val di Chiana. Originally an Umbrian city, it was conquered and enlarged by the Estruscans, who called it Curtun. The prevailing character of Cortona’s architecture is medieval with steep narrow streets situated on a hillside that embraces a view of the whole of the Valdichiana. From the Piazza Garibaldi is a fine prospect of Lake Trasimeno. Parts of the Etruscan city wall can still be seen today. The main streert, via Nazionale, is the only street in the town with no gradient, and referred to by locals by its older name of Ruga Piana. Inside the Palazzo Casali is the Museo dell’ Academia Etrusca, displaying items from Etruscan, Roman, and Egyptian civilizations. Visit the Etruscan chamber-tombs the Tanella di Pitagora. The Diocesan Museum and the Academy Museum include well known artists with paintings such as Maternita of Ecstacy of Saint Margaret. Ther are numerous churches in Cortona, but the ones not to miss are the Santa Maria Nuova and the Santa Maria delle Grazie al Calcinaio.

Tuscan Landscape, Cortona, Italy


Lucca is a graceful and beautifully preserved town whose lovely streets are lined with old houses. and surrounded by vast walls. As you walk through the city you can see a lot of original Roman architecture including the Duomo di San Martino and the Church of San Frediano. See the famous Via San Paolino, the statue of Giacomo Puccini, the Cathedral of S. Marino and visit the Piazza San Michele.  One of the most popular activities is to ride bicycle along the walls to take in the spectacular views of the city.

Montecatini Terme

Montecatini Terme lies at the extreme foothills of the Apennnies. Montecatin has been focuses from time immemorial on its biggest resource: the thermal waters that gush naturally out of the ground. Walk through relaxing tree-lined roads and parks that surround the nine thermal spas. Walk down Viale Verdi, the main central boulevard and look up to the mountain, the beautiful hamlet of Montecatini Alto. Visit Piazza Giusti with its original stone paved floor. The Parlascio is the ancient site of markets and public assemblies, which houses the Theatre of Risorti. See the Provostal Church of St. Peter, whose Romanesque origins are still noticeable into the pillars, the facade and capitals. Don’t miss the monumental fountains spread in the centre of Montecatini.

Twilight at typical Tuscany highland village

Thing to do in Tuscany.

  • Take a break with the locals at a wine bar to sample the excellent Chianti and the Super Tuscans. Enjoy meals prepared by chefs who take the utmost care in preparing the basics and build the delicious courses from there. They have high quality, local ingredients to work with which are the pride of Tuscany.  Learn how to do it yourself at cooking classes during your stay.
  • Be inspired by Renaissance Florence with its overwhelming collection of galleries, churches, museums and public sculpture. You’re surrounded by significant art and architecture at every turn in this fascinating city. See Michelangelo’s David, Brunelleschi’s dome on Santa Maria del Fiore cathedral, works by Donatello, Leonardo, Giotto, Botticelli and so many more.
  • Explore the hills and villages on foot or by bike; stop in at a vineyard for wine tasting or at a farm to sample olive oils; visit Pisa and Sienna; learn Italian or take a fashion course.

Browse our selection of Italy tours.



Montepulciano Country Resort s.a.s.
P.IVA 01125490522 - REA 122445
Via di Montenero, 18
53045 Acquaviva MONTEPULCIANO (Siena, Toscana) ITALY
Tel. + 39 0578768166
Cel. +39 3465034918
Skype: montepulcianocountryresort
Privacy Policy

© Copyright 2016 by Montepulciano Country Resort s.a.s.
Realizzazione Sito Internet: Studio Web - WWS

Facebook Messenger
WhatsApp Chat
Invia con WhatsApp