Tuscany Villages Tour 2026

We meet in Florence and head into the hinterland. The Tuscan countryside is one of the quintessential images of Italy, and the hill-top towns make for excellent visits for either dining or exploring. This is our plan for the week.

Our first stop is the town of Castellina in Chianti, which features a small piazza alongside the 15th century castle. We enjoy the village atmosphere, and make time for a gelato or a coffee.

Next we view an Etruscan burial site nearby, the Tomb of Montecalvario. Etruscans were one of the early populations in Tuscany, in pre-Roman times. This tomb has four chambers partially underground in a burial mound, and was constructed in the 6th century BC.

We then reach our accommodation, a boutique hotel called Tenuta di Mensanello. You will be staying in a 500 year old rural estate, a special experience in which you can feel echoes of the past traditional life all around you. This estate was really a type of farm village, and alongside the beautifully renovated rooms you can see the chapel and the farm buildings.

We spend the afternoon exploring the estate with the owners, seeing their horticultural activities, their rare breeds of livestock, and their vineyard that produces the chianti wine that we enjoy with our dinner together in the evening. We delve into their production philosophies, which are focused on compatibility with their land and the use of heritage varieties.

In the evening we have dinner together in their restaurant right here on the estate. This is our first introduction to the Tuscan cuisine, much of which is grown on the farm right outside our door. This is farm to table at its best. During the week we will continue our exploration of Tuscan cuisine, with a progressive discovery of the local cuisine.

Meals: Dinner

We depart for our first stop, a place called Bagno Vignoni. These are thermal pools that have been used since ancient Roman times. Back then they were prized for their therapeutic properties, and are still well patronised today.

We move on to the town of Montalcino. After a walk through the town centre together, we also leave you some free time to browse the shops and to wander around.

In this part of Tuscany the highly regarded Brunello di Montalcino is produced. We sample this and a range of other wines to accompany our lunch.

After lunch we visit an elegant formal garden. This garden was established in the early twentieth century and has a fascinating history – and it’s not just the botanical history that we find out about.

Meals: Breakfast, Lunch

We spend the day exploring the town of Siena. On a guided visit we look around various parts of town you’ll see how loyal the locals are to their zone – the area that they represent in the palio, the bareback horse race around the central Piazza del Campo. We continue on to see the cathedral, where you discover some interesting quirks of its construction and history. Once the capital of a republic, and arch rival of Florence, Siena has a rich and varied history.

We also leave the afternoon for you to see Siena independently. Most people head to a café for some of Siena’s renowned biscuits such as ricciarelli and cantucci. A great idea is to visit one of the historic cafes of the town centre, such as Caffe Poliziano, which started in the 1800s.

After a break back at our countryside lodgings – a good time for a swim – we venture out for an evening in Volterra. As well as the Etruscan and Roman features here, this is a classic Tuscan hill town. After we see some of the town together, you have time to look around yourself – wandering cobblestone lanes inside the ancient town walls, finding that perfect trattoria for dinner, or just an aperol spritz on the piazza if you prefer.

Meals: Breakfast

This morning we travel to the town of San Gimignano. From a distance we start to see the medieval towers of San Gimignano, erected by the noble families in a bid to out do each other.

San Gimignano is one of Italy’s most well-preserved medieval towns. Perched on a hilltop, it is a commanding presence dominating the patchwork of olives and vineyards in the valley below. San Gimignano’s narrow streets boast many artisan workshops. And there’s a particularly good gelateria in the piazza. While busy in the summer months, our visit is off peak and a great time to be here. You have free time to explore the town independently.

We stop in to the Tenuta di Mensanello to recharge in the afternoon, then head out again for an evening on a lovely property where we spend some time looking around and enjoy a meal of classic Tuscan dishes.

Meals: Breakfast, Dinner

Our first stop is the village of Monteriggioni, a rare example of a town still contained within the original 3th century walls, just as it was centuries ago. The small piazza and old stone buildings are simply charming, this village has a medieval feel. We allow time for you enjoy being in Monteriggioni, and to look around the central village. You can do a circular walk along the top of the town walls to enjoy the fantastic views, or simply relax in the piazza with a coffee or gelato.

Lunch is in a restaurant contained within a 12th century monastery complex, the Monastery of San Salvatore. Originally this would house pilgrims en route to Rome, so we dine in a courtyard that has seen many centuries of monks walk its paving stones.

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

Meals: Breakfast, Lunch