Discover Tuscany: Culture, Food & Wine

Our adventure starts at Hotel Le Renaie, our welcoming family-run hotel in the village of Pancole, just 4mi (6.5km) from the medieval town of San Gimignano. Around 6pm, say ciao to your tour leader and fellow travellers, when we gather as a group to get to know each other and learn more about the adventures ahead. Your tour leader then ensures a big welcome over a group dinner. Please note: On selected dates, there may be two groups at Hotel Le Renaie. Our experienced tour leaders may therefore adjust the itinerary to ensure you enjoy each activity with your own small group. If you wish to extend your adventure, consider booking pre-tour nights in Pisa or Florence. Speak to your sales representative for more information on our pre-tour accommodation and city extension packages.

We begin our exploration of Tuscany by visiting Colle Val d’Elsa, a medieval town well off the normal tourist track and, surprisingly, a world hub for crystal production. After an introduction to the town from our tour leader or a local guide, enjoy free time to stroll through the enchanting streets and explore the local crafts. After lunch, we visit the renowned Majnoni Guicciardini Farm to explore organic vineyards and ancient cellars on a guided tour. Our visit includes a look around the family’s historic villa before we conclude our exploration with a tasting session in the garden or at the ancient olive mill. Back at the hotel, you have the option to dine at the restaurant, which offers a delectable selection of dishes to complete the day’s experiences. Unwind further, perhaps, with a game of billiards or another glass of local wine on the garden-view terrace.

After breakfast, we head to Certaldo station and catch a train to Siena (approximately 45 minutes). This medieval city is dominated by impressive gothic monuments and is divided into 17 contrade (districts), each of which goes head-to-head in the twice-annual Palio, a thunderous horse race around the central square for which the whole city turns out. We join a local guide on a tailor-made tour of the city, stopping at the landmarks, plus captivating sites most tourists normally pass by. Our tour includes a visit to a contrada museum, which is typically closed to the public, and dips into botteghe (small, traditional shops) to sample traditional local sweets. You may also opt to visit the medieval Siena Cathedral (not included). Advance booking is required and available at www.operalaboratori.vivaticket.it/en/tour/complesso-monumentale-del-duomo-di-siena/2589. We recommend a timeslot between 2pm and 3.30pm.

This morning, we drive for approximately one hour along the Chiantigiana, a picturesque route that winds through Chianti vineyards and olive groves. Our destination is Castellina in Chianti, one of the original Chianti Classico villages. Enjoy free time to wander, explore the medieval streets and, perhaps, enjoy an optional wine-tasting experience (payable locally). In the afternoon, we join hands-on cooking class at a locally owned wine estate. Getting into the role with aprons and hats, we master pasta and sauce making, while the menu also features local wine to enhance the culinary journey.

Today is free to enjoy Tuscany at your own pace. If you feel like relaxing, simply stay at the albergo and enjoy the hospitality of our hosts, taking dips in the pool. Alternatively, head to the nearby hilltop town of San Gimignano, which is wrapped in 13th-century walls and has a cityscape punctuated by medieval towers. If you’d prefer something else, your leader can advise on local chianti wine-tasting tours, e-bike and Vespa hire, or offer assistance for unguided walks or daytrips.

Our destination today is Florence, the birthplace of the Italian Renaissance. We reach Florence from Certaldo by train, approximately a one-hour journey. A local guide meets us upon arrival, leading a one-hour exploration of the city, delving into the captivating tradition of the ancient wine windows (buchette del vino). Strategically placed on the walls of city palaces, they were introduced to sell wine without opening a shop, allowing the vendors to avoid paying tax. Though centuries old, many are in use, their popularity increasing after years of being ignored, even by the people of Florence. At the end of the tour, you can purchase a glass of wine to toast our Florence adventure. The rest of the day is free for you to explore the cultural and architectural treasures of the city at your own pace. You might consider a visit to the Uffizi, an art gallery housing masterpieces by Renaissance artists, including Botticelli’s The Birth of Venus and Caravaggio’s evocative Medusa. Today concludes with a traditional Italian pizza night at our hotel.

A 45-minute drive takes us to Volterra: perched on a hill, it is wonderfully picturesque with medieval ramparts, Etruscan roots, and panoramic views of the countryside. Take the opportunity to visit landmarks such as the first-century BCE Roman theatre or the Cathedral of Santa Maria Assunta. Alternatively, wander through the streets, discovering artisan workshops – the town is well-known for producing handmade alabaster objects. In the afternoon, we return to Pancole and visit the family-run Cesani estate. Nestled in the scenic countryside, it produces some of the finest wines in Tuscany. Our visit includes an expertly led tasting, in which we savour three glasses of their exquisite wines paired with bruschetta, extra-virgin olive oil, and a selection of Tuscan cheeses and charcuterie. It’s a sensory journey that not only showcases the estate’s craft but also provides a taste of the distinctive flavors and traditions that define this captivating corner of Tuscany. It’s then back to our albergo for a farewell dinner, a chance to relax with new-found friends and reminisce about the adventures we’ve shared together.