Tuscany Walks & Chianti Wines

Start at Hotel Le Renaie, our welcoming family-run hotel 4mi (6.5km) from 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. If you have extra days at hand and wish to extend your adventure, consider booking additional nights in Pisa or Florence. Speak to your sales representative for more information.

Get ready for a day full of history and nature as we explore one of the most popular sections of the Via Francigena, which links the villages of Gambassi Terme to San Gimignano. The Via Francigena is an ancient pilgrimage route that links Canterbury in the UK to Rome; the full trip takes well over 90 days, but our section is far gentler, cutting through olive groves and vineyards. Later in the afternoon, we head to Azienda Agricola Pietralta, a picturesque farmhouse in the heart of the countryside, where we enjoy three glasses of wine and a trio of cheeses. Dinner this evening is back at the hotel, where we have time to relax, perhaps with a game of billiards or another glass of local wine on the garden-view terrace.

Start our scenic walk from Fonterutoli, surrounded by the rolling hills, vineyards and olive groves of the Chianti region. At the beginning, we enjoy beautiful views towards Siena before following part of the historic Via Romea, an ancient pilgrimage route to Rome. Along the way, we may pass near the remains of an Etruscan necropolis, offering a fascinating glimpse into the ancient past of the area. Finishing the hike, we transfer to Castellina in Chianti, a charming hilltop town known for its medieval atmosphere, stone streets and strong connection to the Chianti wine tradition.

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. You may also opt to visit the medieval Siena Cathedral. In the afternoon, learn about Tuscan wines during a one-hour lecture in the courtyard of Palazzo delle Papesse. Unlike traditional wine tastings, this expert-led experience is more educational, offering in-depth insights into Tuscany’s most important wines.

Today is free to rest by the poolside. Alternatively, your tour leader can advise on local chianti wine-tasting tours, cooking classes, e-bike 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. Most of the greats from the movement lived or passed through here: Leonardo da Vinci, Michelangelo, Sandro Botticelli and more. Learn all about it by joining a guided exploration, which your tour leader can help to organise. Join one of the morning tours and you’ll have time to visit the Uffizi, an art gallery housing works by Renaissance masters, including The Birth of Venus by Botticelli and the gruesome Medusa by Caravaggio. If you do wish to visit, we recommend prebooking your ticket online to avoid lengthy queues. An ideal time is around 2pm if you’re joining the morning walking tour. Tickets can be purchased at www.uffizi.it/en/tickets.

Take a short transfer to the medieval town of San Gimignano, where we can visit the Palazzo Comunale, a 13th-century stone palace that’s home to the Pinacoteca (Art Gallery) and 177ft (54m) tall medieval Torre Grossa (you can purchase the €15 entrance ticket locally). There’s free time to wander and soak up the atmosphere. Before your farewell dinner, we visit the family-run Cesani estate, which produces some of the finest wines in the region. Here we enjoy an expertly led tasting, sampling three glasses accompanied by bruschetta, extra-virgin olive oil and a selection of Tuscan cheeses and charcuterie.