Compiling this list is so very hard! Tuscany has thousands of little villages and towns, the vast majority of which are true gems in the countryside. Just by traveling along a freeway crossing Tuscany allows a wide range of beautiful panoramas spacing across miles of hilly lands covered with cultivated fields. The undulating profile of the view is often interrupted by characteristic Tuscany villas and dotted with towns resting on top of major hills. At night the spectacle is even more impressive. Which ones should you visit? Here are the top ten must-see towns in Tuscany.
San Gimignano
A must see, just 20 minutes from Siena, San Gimignano is a UNESCO world heritage site. Its towers fill the sky from a distance, and its heart is a delicious treat for the eye, thanks to carefully preserved medieval palaces, squares and homes. Stop by a winery, sit outside and sip a nice glass of Vernaccia!
Pienza
The birthplace of Renaissance. This small crown-jewel in the Valdorcia sits atop a panoramic position, commanding 360-degree views of unmatched beauty. The Pope Pius II Piccolomini was born here and wanted it to become an important political center. It is the ideal Renaissance city, but thankfully it was never developed to its fullest. Walk through its winding alleys getting lost within its romantic essence!
Pitigliano
Its Etruscan origins and singular position on a large flat rock boulder give to Pitigliano so much character and charm that you will feel like buying a home here. A mixture of peacefulness and charming glimpses underlined by a daily routine made of simple things. Absolutely the place to relax.
Montepulciano
The town of wine and art. Here you can taste one of the most ancient wines in the world, the Nobile di Montepulciano. The Etruscans were already making wine on these lands! The town’s characteristic is to be all perched on a hill with alleys that wind from main streets into squares while passing through red roofs and flowered terraces with sleepy cats. The intricate architecture is splendid. DO not miss the Bravio in August!
Gaiole in Chianti
This is the home of Chianti Classico. It is here that Baron Ricasoli created the official formula for Chianti wine. It’s Forbes magazine favorite place to live and a number of splendid sites can be found around here. Do not miss the Coltibuono Abbey and the Brolio Castle.
Populonia
A tiny group of houses surrounded by a ring of walls. Populonia still preserves its ancient Etruscan plan. It can be found along the coast of Tuscany perched on a cliff overlooking the wonderful Thyrrenian sea. Here you have the impression of being in another time, yet there are all the comforts for a vacation in Tuscany.
Porto Ercole
A delicious fisherman town unrolling from a hill into the sea. The houses on the sea display their humble origins, yet are the most charming trait. Higher on the hill more imposing buildings, such as the Governor’s Palace, sway up imposing their presence. It is here that Caravaggio died during his return to Rome. A local church still hosts his remains. If you are looking for a seaside vacation, this is the perfect spot to look for Tuscany hotels to spend an authentic holiday in Italy.
Civitella Val di Chiana
Near Arezzo and Anghiari rises this unique little gem that was saved from abandonment. You will find it perched on a hill of the Tiber Valley ready to give you unforgettable memories of its intricate pattern of cobble alleys and stone-wall houses. If you cannot find an apartment in town you are sure to find Tuscan villas for rent in the immediate vicinities, while arezzo is a stone-throw away.
Monteriggioni
The perfect example of a castle town, Monteriggioni still preserves its antique shape. A luxurious hotel discretely accommodates you in and allows you to live a Middle Age vacation in Tuscany. Every detail was preserved intact, and in July the town returns to its ancient fasts with a Middle Age reenactment including peasant restaurants, markets, battles, jousters, and artisans.
Barberino Val d’Elsa
Set along one of the most scenic state roads, the SS2 through which you should drive from Rome to Florence to enjoy splendid landscapes and towns, Barberino sits atop a hill still surrounded by most of its defensive wall ring. It is a small but well designed town composed of little roads and surprisingly large palaces. From here the views over the Elsa valley are unforgettable.
