This tour is on a wine road connecting famous hilltop towns in a major wine growing area in Tuscany.
Major centers are, Montalcino, home of the famous Brunello wine, Montepulciano, home of the famous Vino Nobile, and Pienza.
(view on the interactive map)

Tuscany - Landscape of the countryside surrounding Montalcino
(photo by gengish; this photo is licensed under the Creative Commons license).

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The splendid “Coast of Circe” (including promontory of Circeo) is around 120 km South of Rome, midway with Naples. The towns of Sperlonga and Terracina along the coastline are rich of archaeological sites dating back to Etruscan and Roman age.
(view on the interactive map)

Latium coastline - San Felice Circeo
(photo by ecabral; this photo is licensed under the Creative Commons license)

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Next to Cinque Terre you have another gorgeous itinerary along the Riviera di Levante, in Liguria. It touches enchantable resorts like Portofino, Chiavari, Rapallo, Camogli, and Santa Margherita Ligure.
(view on the interactive map)

Liguria - Camogli, San Fruttuoso
(photo by Twice25 ; this image is licensed under the Creative Commons)

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A video of Palio di Siena, the famous historic horse race taking place in Siena (July 2 and August 16), one of major art cities of Tuscany.

(via YouTube)