Florence, Siena, and Pisa are the most famous places in Tuscany. But those who dare to take off the beaten track are surprised by hidden treasures. Behind every curve, a medieval town can be seen, original villages on hilltops offer great views, and you never want to leave home with homemade gelato, regional wine and food like an Italian mom.

Lucca

Lucca is the “hidden champion” of Tuscany. The old town is surrounded by a four-kilometer-long city wall that can be hiked. The city center is closed to regular traffic, Lucca is thus a medieval pedestrian area. Through the winding lanes leads to the landmark of the city, the 44 -meter-high tower “Torre Guinigi,” on whose observation deck stately trees grow. In addition to the beautiful architecture, Lucca is also a perfect destination for a shopping tour: those of historic buildings …

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Ascendant Holidays recommends visiting Romanesque Facade and bell tower of St. Martin Cathedral in Lucca, Tuscany.

San Gimignano

Here one travels directly back to the Middle Ages: For since a decree of the duke from the year 1563 in San Gimignano no structural changes have been made.

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Trattoria Osteria restaurant in San Gimignano

The place, 50 kilometers southwest of Florence, is also called “Manhattan of the Middle Ages”.

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Le Filigare vine from San Gimignano

He owes this epithet to the 15 gender towers, which tower up to 54 meters into the sky. They testify impressively the medieval competition of the powerful families around the highest tower.

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Vineyard

Arezzo

This city on the eastern edge of Tuscany is a pearl of medieval architecture. Magnificent patrician houses, merchant palaces, and sacral buildings line the streets and squares. The 11th-century cathedral houses several large glass paintings depicting biblical scenes from the 15th century. Worth seeing is also the remains of the Roman amphitheater with its museum.

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Piazza Grande the main square of tuscan Arezzo city, Italy

Volterra

In Volterra, the entire history of Tuscany is reflected: 50 kilometers west of Siena can be found here the remains of an Etruscan city gate, over 2400 years old. The two stone heads on the side pillars of the gate make the passage of time noticeable, because they are so heavily weathered that you hardly recognize the faces. The Roman amphitheater and the thermal bath were built around the birth of Christ. The Duomo, the Palazzo Pretorio and the Torre del Porcellino prison date back to the 12th century.

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Volterra town, Tuscany

Montepulciano

Built on a hill, from Montepulciano you have a magnificent view over the Tuscan countryside. Located on the eastern edge of Tuscany, 50 kilometers from Arezzo, the “Nobile di Montepulciano” produces one of the best wines in Italy. Also, music festivals for classical music take place in summer. Most of the city’s buildings date back to the Renaissance.

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Historic center of Montepulciano

Pienza

Designed as the ideal city of the Renaissance and commissioned by Pope Pius II in 1459, it impressively proves the architectural genius of the era. In the heart of the Orcia Valley and only 15 kilometers from Montepulciano, the place is a UNESCO World Heritage Site. Streets and squares are laid out geometrically. The cathedral “Santa Maria Assunta” shows Gothic and Renaissance elements in interaction.

Best places to visit in Tuscany

Front view on Santa Maria Assunta’s Cathedral Pio II Square Pienza Tuscany Concattedrale di Santa Maria Assunta cathedral church. Italy

Carrara

Carrara is one of the northernmost towns in Tuscany and famous for its marble, which made Michelangelo’s David among others. Tuscan marble is all about the sights of the city, such as the Marble Museum, the façade of the cathedral and the sculptures scattered all over the city. Who wants to learn more about the extraction of the rock, should not miss a visit to the quarries and marble sawmills. The path leads over an imposing arch bridge over the Vara River.

Orbetello

The town is located on a headland in the Maremma and is almost entirely surrounded by the sea. This “Laguna di Orbetello” is WWF nature reserve and offers a unique habitat, with a little patience you can even observe flamingos. In the lively pedestrian area of the village, small shops and ice cream parlors lined up with homemade gelato. Architecturally, the influence of the Spanish supremacy is well recognized, especially at the city wall, the city gates and the cathedral in Baroque style.

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Orbetello

Anghiari

Here the visitor will find idyllic peace and tranquility. The place 20 kilometers east of Arezzo is part of the “Cittàslow”, a movement that aims to improve the quality of life in the cities. For this, the focus is on regional products and enjoyment is experienced more consciously. The numerous antique shops reinforce the feeling that in Anghiari the clocks run slower. Reason enough for a relaxed walk through the medieval streets and a visit to the cathedral.

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Anghiari Tuscany Italy

Porto Santo Stefano

If you like mixing Italians, this is the place for you. Many Romans and Florentines own summer villas and summer cottages in Porto Santo Stefano. So the town gets a sophisticated character, which harmonizes perfectly with the Italian “dolce far niente.” The village is located on the peninsula of Monte Argentario at the southern end of Tuscany. It has a 17th-century fortress with a drawbridge and a winding old town with colorful facades. In the old port, the luxury yachts line up to match the villas.

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Porto Santo Stefano

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