The intoxicating beauty of Tuscany is there for all to see. But that’s just the start on this gentle small-group hiking adventure. Guided by an expert tour leader, we experience the Garden of Italy through the eyes of a local, staying in the small village of Pancole, where we’re treated to classic Italian hospitality by the Sabatini family. Our walks take us through beautiful vineyards and we explore the Renaissance cities of Siena and Florence with expert local guides. Of course, we also sample several varieties of the local chianti together, forging friendships that could last a lifetime.
Activity Areas
Centre-Based
Foodie Holidays
Walking & Trekking
Walking & Trekking Bestsellers
Region & Country & City
Europe: Italy, Tuscany
Included in the Price
— All breakfasts, five dinners, three wine tastings
— All accommodation
— All transport and listed activities
— Tour leader throughout
— Group arrival and departure transfers available
Not Included In The Price
— Travel insurance
— Single accommodation (available on request)
— Visas or vaccinations
— Local taxes (approx. €10)
Accommodation Information
— Accommodation: 7 Classic nights (Hotel Le Renaie)
— Five days of walking and sightseeing
— Group normally 4 to 16, plus leader. Minimum age: 18
Map
Itinerary
Day 1 Adventure starts in Pancole
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.
Day 2 Walk a section of the Via Francigena • Afternoon local wine tasting
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, 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.
Day 3 Walk in Radda in Chianti
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.
Day 4 Explore Siena • Learn about Tuscan and Italian wines at a wine school
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.
Day 5 Free day to visit other Chianti villages or relax by the pool
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.
Day 6 Discover the magnificent city of Florence
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.
Day 7 Explore San Gimignano • Afternoon wine-tasting
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.
Day 8 Adventure ends in Pancole
You've walked some of the most scenic trails in Tuscany and explored the local wine scene, but now it's time to bid Hotel Le Renaie a fond farewell and begin your return journey home.
Alternatively, speak to your sales representative to extend your adventure and spend more time exploring the Renaissance flair of Florence.
