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Tuscany and Umbria taylor made holidays since 1992

September 19th – Cycling the Tuscan Hills

The cycling above Tuscan Hills, is a cycling tour that unfolds through unique scenaries from Chianti vineyardsto the “Crete” allowing you to visit the most famous art cities of Tuscany and some of the most beautiful abbeys of Italy.

Activity Level: Moderate | Mileage: 270 km | Daily Cycling: 2 – 5 hr

Duration: 7 Days – 8 Nights





Day 1 – Arrival and Settling

Option 1: Overnight in a Villa near Staggia Senese
Option 2 : Overnight in Villa Lecchi near Poggibonsi
where you will be met by our representative who will drive you to your villa in Staggia near Castellina in Chianti



Day 2 – Staggia /Colle Vald’Elsa/San Gimignano – Km 35

Departing from Staggia or Poggibonsi, first you encounter the fortified town of Monteriggioni, its round distinctive shape dominating the surrounding plain; then Colle Val d’ Elsa and its glass blowing artisans some of which you can visit. San Gimignano with its towers will request more time and a couple of hours of window shopping before starting back to your villa.



Day 3 – Staggia/Castellina in Chianti/Siena – 38 Km.

A nice day through winding Chianti roads, in a landscape of luscious, vineyards and superb wineries to end in Siena to have an icecream on one of the most famous squares in Italy: Piazza del Campo.



Day 4 – Siena /Buonconvento – Km 40

A nice day through winding Chianti roads, while the landscape is changing from luscious, vineyards to the more linear cypress-crested hills of the “Crete” near Buonconvento. Murlo is a nice little village on your way to the nice farm where you are spending the night. In summer you will be glad to get a refreshing dip in the swimming pool or in autumn a relaxing massage and a sauna at their beauty farm.



Day 5 – Buonconvento/Montalcino – Km 46

Rather difficult start, with fairly steeps slopes until you reach the asphalt. Then you head for The Monte Oliveto monastery. You will spend the night in a nice hotel in Montalcino the Brunello home land.



Day 6 – Sant’Antimo abbey

Enjoy this fortified town from the bastions of which you will enjoy of a 360° view. The descending trail road lead you to the beautiful and peaceful church of Sant’Antimo where you may be able to listen to Gregorian chants.



Day 7 – Montalcino/Pienza/Montepulciano – Km 45


A very full day as from the thermal square of Bagno Vignoni, to Pienza, the renaissance jewell redesigned by the Pope Pio the II to become a “liveable” town; Visit the town which is also an agricultural centre well known for pecorino cheese, and truffle production. A dirt road will take you to Monticchiello a nice little village immersed in the “Crete”. you can stop ther for a nice lunch or just for a cappuccino before continuing to Montepulciano known for its “Nobile” wine.

Cooking classes available in the last day at Villa Cicolina.



Day 8 – Departure

Transfer to Chiusi train station.




..or organize your own tour!