Region: Tuscany / Filter: city


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Arezzo: About 65 kilometers after leaving Florence you come to a turnoff to Arezzo, located about 10 kilometers east of the highway. Arezzo is still in Tuscany, but since it is so close to Umbria and “on the way,” now is the time for a visit. Arezzo has a rich history dati... more

  • Karen Brown Recommended

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As my husband and I drove southeast of Siena, we became hungry and decided to stop at the next village. Asciano, fortunately, was the next village! We might have been there during siesta time because very few shops were open. We passed a couple of open bars before finding one with eld... more

  • Karen Brown Recommended

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From San Quirico d’Orcia, head south on S2 for about 6 kilometers and watch for a small road to the right leading to Bagno Vignoni. This is a most unusual, very small town, known for the curative value of its hot sulphur springs. In the center of town, you find what would have b... more

  • Karen Brown Recommended

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Recommended by Borgo Giusto: Splendid village on the bank of the Serchio after the Devil’s Bridge Borgo a Mozzano is the first town of the Serchio Valley and is found just before the Magdalene Bridge, an incredible and magnificent medieval structure, the Valley’s true symbol, ... more

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Recommended by Casa Bolsinina: Buonconvento is a small nice village about 25 km south of Siena in Tuscany. Surrounded by medieval walls, it is a interesting place but not too touristy. The townspeople are enjoyable and  the city is known for good Trattorie. Buonconvento is easy to... more

  • Property Recommended

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The ancient village of Colonnata—famous through the ages for its marvelous white marble. As you wander this tiny town you’re following the footsteps of Michelangelo, who used to come to here to choose huge blocks of marble from which to carve his masterpieces.... more

  • Karen Brown Recommended

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Cortona is still in Tuscany, but fits more conveniently into our itinerary for Umbria since it is on the route. Stop to enjoy the atmosphere of this medieval town: its narrow, twisting, cobbled streets, jumble of small squares, lovely boutiques, excellent restaurants, and colorful bui... more

  • Karen Brown Recommended

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Florence, without a doubt, is Tuscany’s jewel. Be generous with your time and do not rush Florence—there is too much to see. If possible travel to the major cities of Italy should be made in the off-season. Even so, be prepared for lines, they are a fact of life.You must, of cours... more

  • Karen Brown Recommended

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Lucca is an ancient, perfectly preserved city. Completely surrounding the town is an enormous wall—a wall so wide that it even supports pretty, small parks and a path that runs along the top that is a favorite for joggers. Lucca is truly a jewel. Take time to wander through her ... more

  • Karen Brown Recommended

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Montalcino, which, along with Montepulciano, is world famous for its superb wine, Brunello di Montalcino. There are many places in town where wine can be tasted and purchased. In addition to wine, the town is famous for its fine honey, which can be purchased in many of the shops. Mont... more

  • Karen Brown Recommended

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Take time to stop in Montefollonico because this is another “sleeper”—a quaint, small, medieval walled town that is fun to explore. For the gourmet, there is a superb restaurant on the edge of town called La Chiusa.... more

  • Karen Brown Recommended

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Montepulciano, a rare jewel of a walled hill town that not only oozes charm in its narrow, cobbled streets but is also center stage for the delicious Vino Nobile di Montepulciano. This wealthy town was home to many aristocrats who built magnificent palaces here. The heart of the city ... more

  • Karen Brown Recommended

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If you are looking for a town that is truly storybook-perfect, none can surpass the tiny, magical hamlet of Monteriggioni. It is such a gem that it is hard to believe it is real and not a creation by Disney! You can spot it from afar, nestled on the top of a small hill, with 14 towers... more

  • Karen Brown Recommended

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Take a small road marked to Monticchiello. You soon arrive at a sweet, tiny, charming walled town whose allure is its unpretentious, non-touristy ambiance. Park your car in the designated area outside the main gate. As you enter through the gate, you will see on your left La Porta, a ... more

  • Karen Brown Recommended

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Recommended by Bosco Della Spina Country Resort: Murlo is situated on a hill at a height of 317 metres, in a commanding position on the watershed dividing the gentle cultivated Crete Senesi and the impervious wooded hills of the Maremma. It overlooks the deep valleys of the river ... more

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Passignano in Chianti is rarely on a tourist route, but we can’t help mentioning this tiny hamlet that exudes such a tranquil beauty. For sightseeing, there really isn’t much to see except the Badia a Passignano Abbey, founded by Benedictine monks in the 11th century. The ... more

  • Karen Brown Recommended

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From Monticchiello, continue on the back road to Pienza. This is one of our favorite walled hill towns in Tuscany, a real gem that mustn’t be missed. The town is perched on the top of a hill and is pedestrian-only so you need to park your car outside the walls. It is no wonder t... more

  • Karen Brown Recommended

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While in Pisa be sure to visit the Piazza del Duomo, a huge square studded by fabulous buildings, including Pisa’s landmark, its Leaning Tower. However, it is not only the Leaning Tower that makes the Piazza del Duomo such a winner, it is studded with many other magnificent building... more

  • Karen Brown Recommended

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Recommended by La Guglielmina: The great attraction of Pitigliano lies in the fact that it is a hamlet completely hewn out of tufa rock. Among a lot of historical testimonies, the Jewish ghetto, due to which Pitigliano was and it is known as "Little Jerusalem." Karen Brown note... more

  • Property Recommended

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Once on your way between Rome and Milan, there are outstanding places to stay and things to see along the coast. However, if your time is strictly limited, choose just one of the three stopovers we recommend (Porto Ercole, Cinque Terre or Portofino) and plan to stay for three nights. ... more

  • Karen Brown Recommended

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The town of Porto Santo Stefano is where the ferryboats depart for the islands of Giglio, Gianutri and Corsica. Beyond the town is a spectacular coastal cliff drive overlooking the sea.... more

  • Karen Brown Recommended

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Located in the very heart of the Chianti wine region, Radda makes a good base of operations. However, not only is the town very conveniently located for sightseeing, it is also extremely quaint and some of its walls are still intact. It was in Radda in 1924 that 33 producers gathered ... more

  • Karen Brown Recommended

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Recommended by La Guglielmina: The Etruscan-Roman city of Roselle is near Grosseto. It has the perimeter walls entirely preserved The various houses,the Forum,the House of the Impluvium and amphitheatre are of significant interest.... more

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Recommended by Salvadonica: Located on a hill, the town of San Casciano val di Pesa is located at the northern edge of the Chianti Clasico region thereby establishing wine as an important factor in its economy.  Archaelogical finds have shown that the inhabitants of San Casciano ... more

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During your exploration of Tuscany, one town you must not miss is San Gimignano. What is so dramatic about San Gimignano is that at one time the walls of the town were punctuated by 72 towers. During the Middle Ages it was a status symbol for noble families to build their own personal... more

  • Karen Brown Recommended

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Leaving Pienza, take S146 west to San Quirico d’Orcia, a very attractive small medieval town with a lovely Romanesque church. If you stop to see the town, you must not miss its lovely garden, called Horti Leonini. An entrance about a block from the main square leads into a tranq... more

  • Karen Brown Recommended

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Recommended by Locanda La Pieve: Semproniano is a small Medieval Village n the herat of Tuscan Maremma, just a stroll from Saturnia hot natural springs. Semproniano is a charatteristic Tuscan and Medieval Village made in the X Century, but old local story and research tell us that... more

  • Property Recommended

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This is an entrancing walled hill town that deserves many hours to savor its rich delights—you should allow yourself at least one full day here. The ramparts are perfectly preserved with a series of massive gates guarding a meticulously maintained medieval stronghold. Drive as c... more

  • Karen Brown Recommended

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Recommended by La Guglielmina: The Necropolis of Sovana is an important archaecological area containing some monumental tombs of great beauty, such as the Tomba Ildebranda and the Tomba della Sirena and the special attraction of the colombarium. This small town was an important vil... more

  • Property Recommended

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Just a short drive from San Gimignano, Volterra is a delightful, non-touristy town enclosed by still-intact, 12th-century walls. Like so many of the cities founded by the Etruscans, Volterra is built upon the flat top of a steep hill. As you drive toward the city, the landscape become... more

  • Karen Brown Recommended