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Vintage Fiat 500

Another way to enjoy the Tuscan countryside is on a vintage Vespa scooter or vintage Fiat 500. A tour of the Val d’Orcia will take you through Tuscany which you are used to seeing on postcards. The road that takes you from Pienza to San Quirico is one of the most beautiful in Italy. Spellbinding views, and well-cared-for roads nestled in the most famous valley of Italy, the Val D’Orcia. Here you will find the famous Chapel of Vitaleta and the house used in the film The Gladiator. Another beautiful route follows the road from Monticchiello to Montepulciano, all bends and cypresses…

When renting a Vintage Vespa I would suggest setting off from Pienza in the morning and heading to Monticchiello for a nice lunch at Osteria La Porta. The restaurant is located at the entrance of the beautiful medieval village of Monticchiello.  Monticchiello is definitely worth a visit as well, perched high on a hill overlooking the valley. The entrance to the village from the Porta Sant’Agata (city gate) offers absolutely stunning views. The village center is dominated by the Church of Santi Leonardo and Christoforo which dates back to the 13th century. Take some time to walk through the church and admire the frescoes while you are here. The locals take great pride in their dwellings. Nearly every home is adorned with blooming pots of flowers and the laundry hanging overhead seems to add to the ambiance of this charming place.

Teatro Povero (Poor Theater)

Another reason to visit Monticchiello is Teatro Povero (Poor Theater). In the Sixties, a unique project of its kind was born, which made Monticchiello more popular among demanding travelers: precisely because there is no theater here, it was decided to create one in the square, a sort of public show that involves all the inhabitants, as actors and spectators.
Teatro Povero performs a different summer show every year, based on a theme chosen by the inhabitants of Monticchiello .


Osteria La Porta serves traditional Tuscan cuisine. There are a number of seats inside and a few outside on La Terrazza dell'Osteria which overlooks the Val d’Orcia, a UNESCO World Heritage Site.  Additionally, they have a very interesting wine list, with over 250 labels mostly from Tuscany, and a wide selection by the glass.


When renting the Fiat 500 it is also a very nice idea to bring a picnic which you can pick up in any of the deli stores in Pienza. As you drive on the tiny picturesque roads you will always find the perfect with an amazing view. You can rent the scooter or Fiat 500 for half a day or a full day or join one of the organized tours.


Vintage Tours Dario Rossi's VINTAGE TOURS Headoffice: Zona Pip - località Fornaci 53026 Pienza (Si) Toscana (Italia) GPS: 43.084859 - 11.677676 tel: (0039) 393 96 55 122 e-mail:

Osteria La Porta Via del Piano, 1, 53026 Monticchiello Italy. +39 0578 755163

Teatro Povero (Poor Theater) Tel / Fax 0578 755118 / Email: / Piazza Nuova, 1 - 53026 Monticchiello (Pienza) /

Olivia Green