Italy: Tuscany Walking Tour

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

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

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. After Buonconvento you will pass by the Tenuta di Capalbio, one of the most famous Brunello di Montalcino estates, which offers wine tastings. 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

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

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

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

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. Enjoy 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, before continuing to the village of Proceno. BLD

Castello di Proceno, Proceno

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