Tuscany Villages Tour 2027

We meet in Florence and head into the Tuscan countryside, an area that defines the classic imagery of Italy — rolling hills, vineyards and hilltop towns.

Our first stop is Castellina in Chianti, centred around a small piazza near a 15th-century castle. Here we take time to enjoy the village atmosphere, perhaps with a coffee or gelato.

Nearby, we visit the Etruscan Tomb of Montecalvario, dating back to the 6th century BC. This burial site, with its underground chambers, provides insight into one of the earliest civilisations in Tuscany, long before Roman influence.

We continue to a countryside restaurant for lunch, introducing you to Tuscan cuisine — simple, seasonal dishes closely tied to the surrounding land.

In the afternoon we visit Volterra, a classic hill town with both Etruscan and Roman heritage. After exploring together, you have free time to wander the cobbled streets, visit artisan workshops specialising in alabaster, or relax in the piazza.

We then continue to our accommodation in Colle di Val d’Elsa, where the medieval town centre sits just outside our hotel.

Meals: Lunch

This morning we travel to San Gimignano, known for its medieval towers that dominate the skyline. Built by rival noble families, these towers remain one of the most distinctive features of the town.

We explore the town together, including some lesser-known areas, before giving you time to experience it at your own pace — from artisan workshops to gelaterias and panoramic viewpoints.

We then head to a countryside villa for a hands-on cooking experience. Here, under the guidance of a local chef, we learn the fundamentals of Tuscan cuisine — from ingredient selection to preparation techniques.

We explore the property, harvest seasonal produce, and prepare a meal together before sitting down to enjoy it.

Meals: Breakfast, Lunch

We begin in Siena, exploring the city with a guided walk through its historic centre. You’ll learn about the city’s districts and their role in the Palio horse race, as well as visit the cathedral and Piazza del Campo.

After time to explore independently — perhaps enjoying local biscuits such as ricciarelli or cantucci in a historic café — we continue to the abbey of Monte Oliveto Maggiore.

This medieval monastery functioned as a self-sufficient community and remains active today. We explore its structures and learn about monastic life, including the production of goods such as wine.

In the afternoon we arrive in Pienza, a Renaissance town redesigned in the 15th century under papal direction. Today it offers a combination of architectural harmony, local food shops, and a relaxed atmosphere.

Meals: Breakfast

We begin at Bagno Vignoni, where thermal waters have been used since Roman times. The central pool and surrounding buildings create a unique setting that reflects its long history.

Next, we visit a rural flour mill, where traditional methods are still used to process locally grown wheat. After seeing the milling process, we enjoy a lunch featuring pasta made from the flour produced on-site, along with other estate-grown produce.

We then travel to Montepulciano, a town known for its wine production, particularly Vino Nobile di Montepulciano. We visit a winery and historic cellars, tasting a selection of wines and learning about the region’s winemaking traditions.

Meals: Breakfast, Lunch

Our final stop is Monteriggioni, a small village still fully enclosed within its original medieval walls.

We spend time exploring the village, whether walking along the walls for panoramic views or relaxing in the central piazza.

Lunch is in a restaurant located within a 12th-century monastery complex, once used to house pilgrims travelling to Rome. The setting reflects centuries of history and offers a fitting final experience.

After lunch, we return to Florence, where the tour concludes in the afternoon.

Meals: Breakfast, Lunch