Today arrive at leisure into the old town of Volterra. Built on a high plateau, Volterra was once a trading powerhouse and although the old town is only a third of its original size, it is a joy to explore. Wander through a maze of cobbled streets, crammed with gorgeously preserved Etruscan, Roman and mediev

Today arrive at leisure into the old town of Volterra. Built on a high plateau, Volterra was once a trading powerhouse and although the old town is only a third of its original size, it is a joy to explore. Wander through a maze of cobbled streets, crammed with gorgeously preserved Etruscan, Roman and medieval architecture. Later in the evening, you will dine at a nearby restaurant to your hotel.

Accommodation: Hotel Volterra Inn
Located within the 5th-century walls of historic Volterra, the hotel is classically yet simply designed. All the rooms have an en-suite and there is a hotel bar open in the evenings, where you can enjoy an Aperol Spritz.

The day starts with a private transfer to the trailhead near Podere Fontanelle. Follow rural trails through the woodland of Castelvecchio nature reserve and into the sleepy hamlet of San Donato, nestled in the classic picture-postcard landscape. Nearing San Gimignano you’ll begin to see its Manhattan-like skyline of medieval towers. One of the most visited villages in Italy, the UNESCO listed historic centre is incredibly well preserved and is a step back in time to when the aristocracy of the 12th and 13th centuries flaunted their wealth by constructing the most elaborate of towers.

Walk: 16km
Ascent: 250m
Descent: 530m
Meals included: Breakfast
Accommodation: Hotel la Cisterna
Overlooking the Piazza Cisterna, the property has been at the heart of San Gimignano for over 1000 years. Rooms have views of the cobbled square, buzzing with life, or looking out over the vineyards and rooftops of the countryside. Restaurants and bars are only a few steps away and as you’re here for 2 nights there is also an opportunity to visit Gelateria Dondoli, a previous winner of the world’s best gelato shop.

Immerse yourself in classic Tuscan countryside as you spend the day walking through the villages and vineyards east of San Gimignano. Follow the traditional white gravel roads (strade bianche) which are a defining feature of Tuscany. Pass through the historic settlements of Poggio Casaglia and Poggio Alloro where you can enjoy a picnic under the olive trees or have lunch in a traditional Fattoria. On return to San Gimignano, you’ll soon see the familiar towers before arriving into the bustle of the historic centre.

Walk: 16km
Ascent: 500m
Descent: 500m
Meals included: Breakfast
Accommodation: Hotel la Cisterna

Today follow the Via Francigena, an ancient pilgrim route starting in Canterbury, England and finishing in Rome which has been walked by pilgrims since the 6th century. Not long after leaving San Gimignano, you’ll be back enjoying the gorgeous Tuscan countryside, including vineyards, as you head south towards Colle Di Val D’Elsa. This is a beautiful amble through a Tuscan la

Today follow the Via Francigena, an ancient pilgrim route starting in Canterbury, England and finishing in Rome which has been walked by pilgrims since the 6th century. Not long after leaving San Gimignano, you’ll be back enjoying the gorgeous Tuscan countryside, including vineyards, as you head south towards Colle Di Val D’Elsa. This is a beautiful amble through a Tuscan landscape of olive groves and vineyards, the route descends into the new town and shortly after into the charming medieval centre and relaxed piazza.

Walk: 13.5km
Ascent: 280m
Descent: 430m
Meals included: Breakfast
Accommodation: B&B Arnolfo
Located next to Ponte di Campana, the Arnolfo is in the heart of the old town and within a few minutes stroll of the historic sights. Rooms have typical stone walls, timber ceilings and have an ensuite. If you wish to relax you can also take advantage of the guest reading room and small garden.

ndscape of olive groves and vineyards, the route descends into the new town and shortly after into the charming medieval centre and relaxed piazza.

Walk: 13.5km
Ascent: 280m
Descent: 430m
Meals included: Breakfast
Accommodation: B&B Arnolfo
Located next to Ponte di Campana, the Arnolfo is in the heart of the old town and within a few minutes stroll of the historic sights. Rooms have typical stone walls, timber ceilings and have an ensuite. If you wish to relax you can also take advantage of the guest reading room and small garden.

A short transfer takes you to the old town walls of Monteriggioni. Built in the medieval ages as a defence fort against Florence, little has changed since the 13th century, so do take time to explore the ancient ramparts and cobbled streets. Leaving the Monteriggioni, rejoin the Via Francigena as you begin a walk through wooded trails, wheat fields and across the flatlands of Pian de Lago. One final climb heads into the outskirts’ of Siena as you make your way to the finishing point of the elaborate Piazza del Campo.

Walk: 21km
Ascent: 330m
Descent: 260m
Meals included: Breakfast
Accommodation: Hotel Chiusarelli
Round off your week with a night in a typical neoclassical villa dating back to the 1870s. Located in the historical centre, several years ago the hotel was refurbished to a traditional Sienese house, complete with large, beautiful preserved frescos. A charming and fitting end to your walking trip.

Depending on your onward travel arrangements, we’d suggest an early morning stroll around the streets of Siena and the Piazza del Campo before the buzz of the crowds descend into the streets.

Meals included: Breakfast