What To Expect From A Wine Tour In Tuscany

Join Hannah, from the Grape Escapes team, on a wine weekend in Tuscany…

I began along winding roads up and down the Tuscan hills on my way to the stunning Castello di Fonterutoli. Described as a ‘wine resort’, I wasn’t sure what to expect, but this was the perfect balance of Tuscan charm and authenticity.

The opportunity to stay on-site at a working winery

After swinging open the rustic wooden shutters of my room to awe-inspiring views and the sounds of nature, I ventured out to explore the village and acquaint myself with my surroundings. However, ‘village’ is not the best way to describe it. Castello di Fonterutoli is a cluster of old stone buildings, effortlessly beautiful in that wonderfully timeworn, only-in-Italy kind of way, in the middle of the Tuscan countryside. A gently winding road weaves its way through the middle and connects Fonterutoli to the larger villages that surround it, such as Castellina in Chianti. Siena is only a twenty-five-minute drive south.

Guestrooms are scattered throughout the village, offering peaceful seclusion and a sense of home. It doesn’t feel like a hotel in the traditional sense – more like a welcoming, family B&B that just happens to have an award-winning winery, wine bar and gastronomic restaurant on site. It’s the kind of place where you settle in quickly and feel you could stay forever. A stay that perfectly represents the Tuscan way of life.

Private tours of premium wineries

As early evening rolled in, I wandered to the edge of the village and peered through a line of cypress trees for my first glimpse of the winery of Castello di Fonterutoli. Home to the prestigious Mazzei family since 1435, the winery carries an impressive history into its 21^st-century winemaking practices. Twenty-six generations of the Mazzei family have worked here, along with a wider team, to continue producing world-class Chianti Classico wines and maintaining the legacy of their family – recognised as being part of the creation of the renowned Chianti Classico.

The winery was renovated in 2006 as an arc-shaped silhouette that looks as though it is sinking into the ground, surrounded by orderly rows of vines. Designed by a member of the Mazzei family, the winery is innovative and environmentally conscious, with its building design playing a significant role in the winemaking process today.

I was welcomed by Tommaso, who took me on a private, guided tour through the winery and described the winemaking process as he went. Castello di Fonterutoli is a gravity-flow winery, which means that gravity gently moves the wine from one stage to the next, complemented by the design of the building. In harvest season, grapes are hand-picked and scanned all day every day to allow for only the very best grapes to be selected, before they are channelled through an opening in the floor to enter the stainless steel vats. This way, fermentation starts naturally. The cellar is fifteen metres below ground, and holds more than 3000 oak barrels. Temperature and humidity are regulated by natural water streams that flow through the limestone rock walls, impressively exposed for you to see.

As Tomasso guided me round the cellars, explaining the process and answering my questions, I came to appreciate how wines are made, which is the perfect appetizer to the tasting experience that lies ahead. We know the wine makes the wine holiday, but nothing makes the wine taste better than witnessing the hard work that has gone into producing every single bottle.

VIP wine tasting experiences

After the tour, we made our way back upstairs to the beautiful tasting rooms. The largest one, which you will taste in if you visit as part of a group, boasts outstanding panoramic views over the vineyards and Tuscan hills. I was welcomed into the smaller, intimate tasting room – where you’ll be on a private tour. As one of Italy’s oldest family vineyards, the legacy of the Mazzei family’s wine carries through to today. Tommaso took me through the tasting process and explained the intricacies and differences between each of the Sangiovese-based wines that I tasted, such as the grapes used in the production process, and how the process differs depending on ageing and any other factors.

Tasting dinners providing unforgettable memories

Following this wonderful tour, I made my way back up the cypress-tree-lined hill into the village, where dinner was waiting for me at the resort’s gourmet restaurant, the Osteria di Fonterutoli. This was a true highlight of my trip: a friendly welcome, top-level service, and most importantly, excellent food. I enjoyed a five-course tasting dinner, each course bringing out the best of the local produce of the region and perfectly paired with a different wine from Castello di Fonterutoli or one of its partner wineries.

Exploring beautiful villages surrounded by vineyards

On day two, after indulging in a delicious breakfast, I was met at the reception by my driver for the day, who was to accompany me through the vineyards. Tuscany is a vast geographical area and very rural, so a private transfer is the ideal way to get around. Grape Escapes’ drivers are English-speaking regional experts – so they can tell you about the area as you drive through and answer any questions you may have. We also made some stops along the way to explore quaint villages such as Castellina in Chianti and Radda in Chianti. Over the course of the day, I visited two more wineries in the Chianti region, which provided a fascinating contrast to the refined Castello di Fonterutoli.

Taste local wines paired with food

Castello Monterinaldi is a Chianti winery with a quirky, modern ethos. In place of a family crest, the symbol of Castello Monterinaldi is the turtle. They embrace the philosophy of slow, intentional growth, with the intention of remaining deeply connected to their roots, land, and traditions. Producing some 90,000 bottles a year, grapes are exclusively picked by hand in late September and early October in order to gather the grapes in the best condition for winemaking and to allow for special selections.

Following my insightful tour of the cellars (with a glass of sparkling rosé in hand), I was welcomed into the 19^th-century villa in the grounds of the winery for lunch. The villa still retains many of its period furnishings making it a pleasant and unique setting for a three-course Italian lunch – accompanied by three of the estate’s wines. After lunch, I enjoyed tastings of some further Chianti wines accompanied by cheeses at another winery in the Chianti region, before heading onwards to Siena.

Combine the vines with a visit to your favourite city

The Chianti vineyards are located an hour or so’s drive from Siena, making it a must-see as part of any Grape Escape in the region. A visit to Siena is like stepping into a beautifully preserved Renaissance painting. There’s a slower pace of life here, despite it being a major city, where days are spent wandering cobbled streets, admiring the striking Piazza del Campo, and sipping local wines in tucked-away wine bars. Whether you’re exploring the magnificent Duomo, browsing artisan shops or enjoying a relaxed, wine-paired lunch just outside the city walls, Siena offers a wonderfully authentic slice of Tuscan life.

This was the perfect place to conclude my weekend in Tuscany, the kind of break that refreshes your spirit and leaves you quietly plotting your return.

Whether, like me, you’re looking for a short escape, or have time for a more extended adventure, Grape Escapes can help create something truly special. We specialise in bespoke, which means your dedicated Luxury Travel Consultant will take the time to understand what your perfect wine holiday looks like — then bring it to life. You can also explore our range of tours online for inspiration and ideas on what’s possible. Don’t hesitate to get in touch at in**@**********es.net or +44 1920 468666 to start planning.