Italy: 5 Places To Visit When You Take A Tour Of Tuscany

Tuscany is beautiful and a part of the world that will always hold a special place in our hearts. It is the first destination we travelled to as a couple a mere 3 weeks after meeting back in Dec 2006. Having never visited Italy before let alone Tuscany, the wonder that was awaiting us was certainly not expected. People thought we were packing our bags and heading to a new country with a stranger was crazy and it’s true when we decided to take a tour of Tuscany, little did we know it would be the start of something wonderful – not only our own love affair but also our love affair with travel.

History and Art

Because of the rich history of Tuscany, it is the perfect place to head if you love submerging yourself in times gone by. Tuscany is steeped in history dating all the way back to the Etruscans in 900 BC. Add into the mix Medieval times, the middles ages and of course the Renaissance and you have an open-air museum proudly displaying architecture and art in plain sight. Of course, there are dedicated museums and galleries showcasing some of Tuscany’s most famous works. These include masterpieces by Michelangelo, Botticelli, Leonardo da Vinci amongst others. However, the churches, buildings and piazzas themselves located throughout the villages, towns and cities are some of Tuscany’s finest sights.

Food and Drink

Food and drink is also a massive part of Tuscany, Tuscan culture and the Tuscan way of life. With rolling fields and vineyards, often as far as the eye can see, the wine from this area is well known and well-loved not only in Tuscany but also around the world. With the added bonus of delicious and often traditionally made food (breads, pasta dishes and of course gelato) being easy to find and plentiful, Tuscany is a dream come true for foodies.

Travel Around Tuscany

There are many ways to travel around Tuscany. But, for us, the only way we even considered was by train. We had heard good things about trains in Italy and they did not disappoint. We booked each journey as we took it. However, looking back it may have been more cost-effective to have bought a Eurail Italy pass (or similar). They allow you to travel for so many days within a one month period. They were reliable, efficient and the scenery as we whizzed through the Tuscan countryside was breathtaking.

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Deciding on a route through Tuscany is the toughest part of the trip. With so many beautiful destinations choosing which ones to visit can be difficult. Each has something different to offer and unless you are not restricted by time or money, you will have to narrow them down to just a handful. Here are 5 of the top places to visit when you take a tour of Tuscany.


view of Cortona, medieval town in Tuscany, Italy

Located in the province of Arezzo, Cortona is a hillside town, it is one of the main cultural and artistic centres of the Val di Chiana (Chiana Valley). The medieval steep narrow streets are ideal for exploring and offer great panoramic views over the town and across the valley. The main road in Cortona, via Nazionale, is the only street in the town which is flat. Many locals refer to it by its older name (possibly original name) Ruga Piana.

Rich in Etruscan roots, the town is a great place to visit if you want to find out more about the area during the Etruscan civilisation and period. Cortona is home to a number of museums which allow you to see artefacts from throughout the town’s history. These include the Musea Maec Etruscan Museum, Diocesano Museum and Monastery Le Celle together with Fortress Del Girifalco, Museum of San March Church and Museum Ai Borghi.


Florence Cathedral in Florence, Tuscany, Italy

No visit to Italy is complete without taking a trip to Florence, therefore it is a must if you take a tour of Tuscany. As the capital of Tuscany, Florence has a lot to offer visitors (and it is, without doubt, one of the most beautiful places we have ever visited). We loved it so much following the first visit we have returned since and hope to take our children as soon as possible too. Florence is a UNESCO World Heritage Site where the streets hold as much history as the museums and galleries do. But that’s not to say you shouldn’t visit some of the wonderful museums in the city.

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The Accademia Gallery to see Michelangelo’s David is a must, to see the world’s most famous sculpture in all his glory (literally) is something else. Other museums worth the entrance fee include The Uffizi Gallery, the Bargello Museum and the Leonardo da Vinci Museum. The Cathedral of Santa Maria del Fiore (Duomo di Firenze) is also a must when in the city. As is a walk across the Ponte Vecchio and (over) indulging in the magnificent food and drink found in the city. Perhaps even take a cooking class if you have the time?


San Biagio church and Montepulciano town in Tuscany

Famous worldwide for producing the Montepulciano d’Abruzzo wine, which is a medium-bodied red, Montepulciano is a medieval hilltop town which is surrounded by vineyards. This makes it the perfect place if you want to take a wine tasting tour in Tuscany where a knowledgeable local will guide you through the local vineyards allowing you to sample the wines they produce. Montepulciano is also famous in the area for its food including pork, cheese, “pici” pasta, lentils and honey.

for a small town, it has a lot of wonderful things to see. These include the Palazzo Comunale (City Hall) designed by Michelozzo, the Santa Maria Assunta Cathedral (Duomo of Montepulciano), which was built between 1594 and 1680 and the Museo Civico di Montepulciano which is located in the Palazzo Neri Orselli, displaying works by the Della Robbia family. The highest point of Montepulciano is the Tower Hall, which overs views across the town and the valleys beyond.

San Gimignano

Piazza della Cisterna in historic San Gimignano, Italy

Located in the province of Siena, San Gimignano is a walled medieval hill town. Here you will find both Romanesque and Gothic architecture. The town is famous for saffron and golden ham (“Tuscan style” pork) and also for the white wine, Vernaccia di San Gimignano. It is produced from the local Vernaccia grapes grown in the numerous vineyards in the area. Many also refer to San Gimignano as the Town of Fine Towers. This is because of the preservation of 14 of its tower houses. These are:

  • Campanile della Collegiata
  • Torri degli Ardinghelli
  • Torre dei Becci
  • Torre Campatelli
  • Torre Chigi (1280)
  • Torre dei Cugnanesi
  • Torre del Diavolo
  • Torre Ficherelli or Ficarelli
  • Torre Grossa 
  • Torre di Palazzo Pellari
  • Casa-torre Pesciolini
  • Torre Pettini
  • Torre Rognosa
  • Torri dei Salvucci
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San Gimignano’s main square is the Piazza della Cisterna. It is triangular in shape with houses and medieval towers around the outskirts. The town is also home to a number of churches. The main church in San Gimignano is the Collegiate Church of San Gimignano located in Piazza del Duomo. It is famous for its murals and paintings. These include works of famous artists including Taddeo di Bartolo, Domenico Ghirlandaio and Lippo Memmi.


Torre del Magnia Tower Piazza Campo Square Siena

Located in central Tuscany, Siena is a must when taking a tour of the region. This beautiful medieval city is a perfect place to spend a couple of days exploring. Especially if you want to learn more about Tuscany’s history. Siena is a UNESCO World Heritage Site and is famous for food, art, architecture and museums. The Saina tribe first settled in the area in the time of the Etruscans (c. 900–400 BC).

The city’s top attractions are located between the must-visit locations of the Piazza del Campo (the main square) and the Duomo di Siena (Cathedral). These include the Torre del Mangia, the 102-meter tower which overlooks the Piazza del Campo. If you opt to climb to the top, the reward is breathtaking views across the city. Together with the Santa Maria Della Scala, which is located right in front of the Duomo. It is one of the oldest hospitals in Europe which it is now a museum.

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