Tuscany Walking Tour / NEW!

Seven nights; seven days of walking an ancient pilgrim route through the hills of Tuscany
“Scenery was fantastic, everywhere I looked it was another postcard shot!” – Kay P.


Start: Siena, Italy, 15:00

Finish: Orvieto, Italy, after breakfast

Day 1


Pick-up at the Siena train station at 15:00 (or contact us for pickup at Poggibonsi train station at 16:00) for a transfer to your idyllic hideaway in the Renaissance gem of San Gimignano, a town of medieval towers high in the Chianti hills. D (Meal inclusions provided for guided trips. Self-guided trips include breakfasts)
Hotel La Cisterna, or
Hotel L’Antico Pozzo, San Gimignano.

Day 2

San Gimignano to Monteriggioni, 31 km

Depart from San Gimignano with a sense of the Romanesque art and architecture that the area is famous for; highlights are a 12th century church, the Duomo di San Gimignano, and 13th century stone walls around the Piazza della Cisterna. In the year 990, archbishop Sigeric travelled between Rome and Canterbury, England, along this route travelling back from Rome, where he received the Pallium from the Pope. Villages along the way today were part of his itinerary: Badia a Coneo, Gracciano, Strove, and Abbadia Isola. Enter the old walled town of Monteriggioni through the Porta Franca gate. BLD
Borgo San Luigi, or
Hotel Il Piccolo Castello, Monteriggioni.

Day 3

Monteriggioni to Siena, 21 km

Fields of sunflowers, vineyards and olive groves are plentiful as you pass by the abandoned Medieval village of Cerbaia. The crumbling remains of the Romanesque abbey still endure, and castles built of stone dot the surrounding hilltops. The ruins of the Rocca of Cerbaia are mysterious looking stone walls, worth closer inspection. As you continue through the miles of vineyards it is evident that you are in the wine country of Chianti. Continue through forested areas and along a river bed to Porto Camollia, the traditional access to Siena from the north. Siena, a UNESCO World Heritage Site and your resting place tonight, is famous for its Palio - horse races that have taken place in the city twice a year in the Piazza del Campo since the 1300s. Enjoy an independent dinner this evening as you wander around the piazza. BL
Albergo Chiusarelli, Siena.

Day 4

Siena to Ponte d’Arbia, 26 km

As you leave Siena, you’ll pass through the region called “Le Crete”, defined by the distinctive grey-coloured Senese clay which gives the landscape a lunar appearance. On the way to Ponte d’Arbia you’ll encounter the majestic beauty of Monte Amiata, one of Italy’s largest lava domes, and pass through the gentle cultivated hills and gullies of Val d’Orcia. Explore La Grancia di Cuna, a medieval farm fortified to protect its grain reserves from political and military instability in the 14th century. At the time, fortified country barns were known as ‘Grancia’. Characterized by its red brick walls, the farm now stands as one of the most interesting structures in Tuscany. A short transfer will take you to your luxury inn for the evening. BLD
Villa Armena, Buonconvento.

Day 5

Ponte d’Arbia to San Quirico, 26 km

Start the day with a morning wander through one of Italy’s most beautiful villages, Buonconvento (comes from the Latin “bonus conventus” which means “happy, lucky place”). Travel back in time through the village center with its wonderful museums, artwork, and the church of San Pietro e Paolo and the Oratorio di San Sebastiano. On your way to Torrenieri, the views of La Val d’Orcia are breath taking; the colours of gold, brick red, brown, and olive green throughout this valley have served as inspiration for Sienese artists for centuries. Upon arrival in San Quirico - a village known for its church built in the 8th century, Collegiata di San Quirico - botany lovers should visit Horti Leonini, a cherished classical Italian garden. BLD
Hotel Relais Palazzo del Capitano, San Quirico d'Orcia.

Day 6

San Quirico to Radicofani, 32km

Today’s walk travels to the southern-most part of La Val d’Orcia, and you will soon see why this region has been designated as a World Heritage Site by UNESCO. The valley and its Orcia River is known for its high quality artisanal products such as pecorino cheese of Pienza, olive oil, saffron, mushrooms, and chestnuts. While most villages in this area have main squares (piazzas) as public gathering places, Bagno Vignoni has a 1500 sq metre thermal pool! At day’s end you’ll come to the end of the valley and the hilltop town of Radicofani, with its dominating castle tower, before being transferred to your nearby inn. BLD
La Gustea Hotel & Cucina, Sarteano.

Day 7

Radicofani to Acquapendente, 24 km

Before leaving the village, make time to stroll through the Bosco di Isabella, a fascinating garden built by the Luchini family in the late 1800s. Continue on the final downhill portion of the Via Cassia, with its magnificent views of Monte Amiata. Arrive at the bottom of the Val di Paglia and the Ponte Gregoriano, an impressive bridge that was rebuilt from the original rubble after WWll. A brief final climb ends your 160 km journey of the Tuscan countryside, in Acquapendente, followed by a short transfer to your inn. BLD
Castello di Proceno, Proceno.

Day 8


After breakfast, transfer to nearby Orvieto train terminal. Departures to Florence (2 hours) or Rome (1 hour) run regularly. B


Note about the route:

Walks range from 21-32km a day on rural trails and secondary roads. Good sturdy footwear and walking poles are recommended., A reasonable walking pace must be maintained to cover some of the routes. Drinking water and washrooms are available only in populated areas.

Tuscany straddles the Apennine hills in the heart of Italy, where cypress trees, olive groves, vineyards, and soft, verdant hills create a landscape reminiscent of Renaissance paintings. Giotto, Michelangelo, and Leonardo da Vinci travelled these same landscapes centuries ago, and fortunately, not much has changed. Their influence is evident in many towns and villages along the route, and as you walk the quiet route along sun-drenched ridges, you will enjoy expansive views over the landscape of their inspiration. For 1000 years and more, pilgrims have travelled La Via Francigena from Northern Europe to Rome. In Tuscany the path stretches through the hills on mule tracks, rural and secondary roads, and cypress lined gravel paths. You will have ample opportunity to sample wine, honey and olive oil, as well as being fuelled by the gastronomic indulgence of some of the region’s finest chefs. Repose in small inns known for their character and charm, and fall in love with the area which D.H. Lawrence referred to as "the perfect center of man's universe".

Map & Elevations

Click for the elevation profile

Day # Daily distance

Learn more

Spend a week before or after you tour exploring other parts of Italy and Western Europe.

Join one of our Eastern European tours.

Spend some extra time in Venice or Rome.


US 3535 C 4245

Includes 8 days, 7 nights, 7 breakfasts, 7 light picnic lunches, 6 dinners, guide and van support, maps and route notes, luggage handling, taxes.

US 3075 C 3695

Includes 8 days, 7 nights, 7 breakfasts, maps and route notes, luggage transfers.



All details and pricing are subject to change without notice.