This journey is designed to deepen your connection to the Tuscany through its food and drink, from organic olive oils and pecorino cheese to Chianti wines, seasonal farm lunches and the hands-on cooking traditions shared in kitchens across the region.

We always endeavour to accommodate dietary requirements and take great care in the preparation of meals. However, as meals are provided by a range of local restaurants, we cannot guarantee the complete absence of cross-contamination. Please inform your Signature travel expert of any allergies or dietary requirements at the time of booking so we can discuss the options available to you.

Where meals are not included, your Signature Guide will be on hand with considered recommendations, whether you choose to dine together or enjoy the evening at your own pace.

Explore Castello di Gargonza with your host, Neri, following stone lanes through this privately owned medieval village above the Val di Chiana. Climb its 14th-century tower, associated with the Italian poet Dante, for a closer look at the village’s layered history.

Gather in the garden’s 2 Stone Room for a welcome drink and intimate dinner. The restored village setting offers an introduction to the architecture and hospitality that shape this Tuscan stay.

Join a local family and their trained dog for a truffle hunt in the Tuscan woods. Walk the hills around their home while learning how hunters recognise the conditions that favour different seasonal varieties of this prized ingredient.

Share a home-cooked, truffle-inspired lunch with regional dishes and local wine. The family’s knowledge, passed between generations, brings Tuscany’s woodland food traditions to life far beyond the restaurant table.

Walk through Siena’s historic centre with an expert guide, tracing the city’s medieval character through its streets and piazzas. See the distinctive shell-shaped Piazza del Campo and admire the intricate marble of Siena Cathedral.

Learn how civic pride, faith and artistic ambition shaped this Tuscan city. Its steep lanes and richly detailed facades make the history visible at street level, while the Campo remains a focal point of Sienese identity.

Dine by private invitation inside the medieval Torre di Roccabruna, once among Siena’s tallest towers. A four-course lunch is served high above the city, with views across its rooftops and the surrounding Tuscan hills.

Siena’s towers spoke to the standing of its medieval families. Sharing a meal within one offers an unusually close encounter with that history, paired with a perspective on the city that few dining rooms can provide.

Meet the farmers at Podere Il Casale on a guided walk from stable to dairy. See how their pecorino cheese takes shape and learn about the produce and estate wines made on this family-run Tuscan farm.

Sit down to a seasonal farm lunch that connects the visit to what grows and is crafted here. The encounter gives a grounded view of rural food traditions, from hands-on cheesemaking to the flavours served at the table.

Stroll through Montepulciano’s historic centre, where stone streets and Renaissance architecture crown a hill above the Tuscan countryside. Spend time among the town’s piazzas and facades before entering a local cantina for a curated wine tasting paired with a light dinner.

Montepulciano has long been associated with wine, particularly the local Vino Nobile di Montepulciano. Tasting in a cantina brings that heritage into focus through the region’s distinctive grapes and food.

Taste locally produced extra virgin olive oils in a guided session devoted to one of Tuscany’s defining ingredients. Notice differences in aroma and flavour while learning how olive growing and careful production influence the finished oil.

Olive groves are a familiar part of the region’s hillsides, but a focused tasting reveals the craft behind the everyday table staple. This private encounter invites you to appreciate Tuscan oil for its character, not simply its place in a recipe.

Step inside a Florence restoration lab for a private look at the meticulous work of conserving historic tapestries, textiles and precious objects. Discover the skill and patience involved in caring for fragile pieces of the city’s cultural heritage.

Florence is celebrated for its Renaissance masterpieces, yet preserving art is an ongoing craft. This behind-the-scenes visit shifts attention from finished works to the specialist hands and considered techniques that help them endure.

Explore the roof terraces of Florence Cathedral with an expert guide, following elevated pathways for rare views across terracotta rooftops, narrow streets and the surrounding hills. This privileged vantage point reveals the scale and detail of the cathedral from an unusual angle.

Continue with a guided walk through Florence, connecting its streets and architecture to the artistic ambition of the Renaissance. Together, the rooftop perspective and street-level exploration show how craft shaped the city’s enduring identity.

Share a farewell dinner at Angel Rooftop while Florence spreads out beneath the terrace. The elevated setting offers a chance to take in the city’s rooftops and skyline over an evening meal.

Florence’s historic centre was shaped by the patrons, artists and craftspeople of the Renaissance. Dining above its streets gives this gathering a distinctive sense of place: a final opportunity to savour the city’s atmosphere together rather than an ordinary restaurant stop.

Visit a Chianti winery for a tasting that explores one of Tuscany’s best-known wine regions. Learn about the area’s winemaking heritage and sample its wines in the landscape where they are produced; lunch is included with this experience.

Chianti’s vineyard-covered hills and long-established wine culture make the tasting as much about place as the glass. This optional Signature Day activity is at additional cost and bookable on tour.

Join Castello di Gargonza’s sommelier for a tasting of three distinctive Tuscan wines. Discuss their character and the regional traditions behind them in the setting of the restored medieval village.

This shorter, hosted experience offers a focused introduction to Tuscany through the glass, without a winery excursion. It suits travellers who want to explore local wine while spending more time at Gargonza. The optional tasting is at additional cost and bookable on tour.

Follow a guide through the rewilded woodland around Castello di Gargonza, taking in the quieter natural setting beyond the village’s stone walls. Join a traditional game of bocce to experience a pastime long associated with local gatherings.

The pairing offers two ways to connect with Gargonza: through its surrounding landscape and through a sociable village tradition. This optional Signature Day activity is at additional cost and bookable on tour.

Work alongside Castello di Gargonza’s chef in a hands-on class devoted to making fresh pasta. Learn the techniques behind a Tuscan kitchen staple before sitting down to enjoy lunch.

Preparing pasta yourself reveals the care behind food that can seem deceptively simple on the plate. Hosted within the medieval village, the class offers a practical, convivial connection to local cooking traditions. This optional Signature Day experience is at additional cost and bookable on tour.

Explore Cortona on a guided walking tour, discovering medieval landmarks, tucked-away lanes and broad views across the Tuscan landscape. Raise a prosecco toast before a private visit to the DelBrenna family showroom.

The visit connects Cortona’s long history with a living tradition of jewellery craftsmanship, offering insight into the family’s work and its local roots. This optional Signature Day activity is at additional cost and bookable on tour.