Guided Vacation in Tuscany

A guided private holiday in Tuscany with a local guide sharing deep knowledge of places, history, and art. Hill-towns surrounded by walls and cypress trees, plus countryside vineyards, olive groves, hamlets, farmhouses, and fortified villas — this is Tuscany at its most authentic and unhurried.

Your accommodation is a first-class Tuscan villa hotel with private bathroom, pool, and gardens with vineyards, umbrella pine, and cypress trees. Every morning you wake to these views; every evening you return to the comfort of the same beautiful base.

A full day exploring the Chianti Classico wine region takes you through Castellina in Chianti with its Etruscan origins, Radda in Chianti with its medieval walls, and Gaiole in Chianti — historic market center with fine wines, castles, and parish churches. Wine tasting and lunch at a wine estate reveal why this region is legendary. Medieval Anghiari, claimed to be among the most beautiful villages in Italy, and Caprese Michelangelo — the artist's birthplace — add cultural depth.

The ancient Pilgrims Route leads to Monteriggioni with its intact medieval curtain walls and fourteen towers, plus the sword-in-the-stone at San Galgano. San Gimignano, one of the most spectacular and best-preserved medieval cities in the world, retains 14 of its original 72 towers. The final days bring Cortona — the Under the Tuscan Sun setting — and Arezzo with Piero della Francesca's legendary frescoes. An evening cooking class with dinner and wine tasting at an organic DOCG winery round out this unforgettable experience.