Fly to Pisa; transfer to Hotel Le Renaie, 4mi (6.5km) from San Gimignano (the transfer is approximately 1hr 10min).

Start at Hotel Le Renaie, our welcoming family-run hotel 4mi (6.5km) from San Gimignano. In the evening, our tour leader holds a welcome meeting to discuss the week ahead, give advice on the local area and answer any questions.

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 Fattoria Le Caprine, a farm estate specialising in cheese making, just outside Gambassi. Here we enjoy three glasses of wine, a trio of cheeses and a tour around the farm.

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.

This morning, we enjoy local history in the heart of the Chianti area, covering a scenic circular route. We cut through woodlands, where we can admire the emerald vineyard valleys. In the afternoon, you have some free time to wander around and maybe join an optional tasting of the much-acclaimed chianti classico at one of the many local wineries.

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.

In the afternoon, learn about Tuscan wines during a one-hour lecture at the Tuscan Wine School. 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 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. 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 one of the free local tours, which typically take in the highlights.

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, which we explore, including visits to the Palazzo Comunale, a 13th-century stone palace that’s home to the Pinacoteca (Art Gallery) and 177ft (54m) tall medieval Torre Grossa. 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.

Transfer to Pisa; fly to London.

Please note that at times, especially during summer months, the inbound flight can be late in the evening. In this instance you will have additional time to spend in Pisa. Leader will take care of all arrangements in terms of transport from/to the airport and the city centre and luggage storage. It may also happen that, for logistical reasons, on return we will have to be at the airport earlier than normally scheduled. This will mean a longer waiting time before checking in.

The trip ends after breakfast. Bid Hotel Le Renaie a fond farewell and begin your return journey home.