Pienza

Surrounded by a mosaic of rolling vineyards, slender cypress trees, and olive farms, cosy Pienza is tucked into the stunning Val d'Orcia region of Tuscany. It's a particularly beautiful town in an area of Italy already known for its particularly beautiful towns; laced with all the cobbled piazzas, Renaissance palazzi, and cinnamon-tinted villas you could want.

Pienza tour guides will enthral you with the fascinating tale of a city that might have been – Pienza was the brainchild of Pope Pio II back in the 15th century, intended to be a paradigm for perfect urban planning. Though construction halted after only a few years, traces of the great vision still stand. They come in the form of crenulated church towers and shadowy arcades on Piazza Pio II, and with the elegant loggias of Palazzo Piccolomini, earning the whole town a coveted UNESCO tag!

In the enveloping countryside, and from the terraces that line Pienza's hilly perch, come views of the jaw-dropping Val d'Orcia. This is Tuscany at its most quintessential, a land of wiggling roads lined by slim-cut trees and verdant slopes aplenty. Either settle in for an espresso on the panoramic lookouts of town, or hit the tarmac to hop between vineyards, cheese farms, and other ochre-stone villages nearby.