Tuscany Walks & Chianti Wines Tours and Travel packages | Trip Prices for Vacation, Holiday and Deals Adventures

Start at Hotel Le Renaie, the guide will hold a welcome meeting to discuss the week ahead, give advice on the local area, and answer any questions.

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. 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, 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 a local history in the heart of the Chianti area, covering the scenic route in a circular walk. Cut through woodlands, to admire the emerald vineyard valleys. In the afternoon, wander around and maybe join an optional tasting  of the much-acclaimed Chianti Classico at one of the many local wineries

After breakfast, 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.

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 any tired legs at the poolside. Alternatively, your 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, birthplace of the Italian Renaissance. 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.

Take a short transfer to the medieval town of San Gimignano, to visit 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.

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