<< home Southern Tuscany
destinations passion hotels in Italy hotels in France Walking and cycling holidays
Accommodation   ||   Booking

Walk from medieval Siena to Pienza, the first Renaissance ‘city’ • The best of Southern Tuscany, with its superb art and architecture • Irresistible rolling hills, long views and the picturesquely eroded ‘crete’ • Some of the best wine-producing areas in Tuscany – Brunello di Montalcino and Vino Nobile di Montepulciano • Exquisite abbeys of Sant’Antimo and Monte Oliveto Maggiore
Southern Tuscany:  Itinerary

Day 1
Arrive in Siena

Day 2
Siena to Lucignano
Walking: south from Siena across the open hills of the crete, to Lucignano. (12.8 miles, 6 hrs 30)
Cycling: through farms and vineyards and over a small range of hills to Lucignano. (14.5 or 27.8 miles)

Day 3
Lucignano to Buonconvento
Walking: through pastures, vineyards and olive groves overlooking the Arbia and Ombrone valleys, to Buonconvento. (8.1 miles, 4 hrs)
Cycling: tough route over a high ridge with sensational views. Easier route along quiet roads. (32.8 or 12.3 miles)

Day 4
Buonconvento to Montalcino
Walking: over open hills and through the famous vineyards of Brunello to Montalcino. (12.7 miles, 6 hrs 30)
Cycling: short route: follow the Asso valley then along a ridge up to Montalcino. Longer route through the vineyards of Brunello. (8.4 or 14 miles)


Day 5
Free day in Montalcino


Day 6
Montalcino to Bagno Vignoni
Walking: through the vineyards of Brunello to the superb Romanesque church of Sant’Antimo. Then on to the Orcia Valley and to Bagno Vignoni. (13.8 miles, 7 hrs)
Cycling: a direct route to Bagno Vignoni or a route past the abbey of Sant’Antimo and into the foothills of Monte Amiata. (13.1 or 12.4 miles)

Day 7
Bagno Vignoni to Pienza
Walking: along the Orcia valley then across open farmland to Pienza. (5.6 miles, 2 hrs 30)
Cycling: direct ridge route or longer route descending to the Orcia valley before climbing into open hills. (8.1 or 22.5 miles)

Day 8
Return to the airport

Or extend your trip to Montepulciano

Walk to the centre of the Vino Nobile di Montepulciano wine district via the church of San Biagio. (8.5 miles, 4 hrs)
Cycling: 11.7 or 14.3 miles.

*** Hotel Duomo
Centrally located in Montepulciano.

**** Hotel La Chiusa
*SRS = single room supplement

Shorter 5 day Itinerary

Buonconvento to Pienza. One night in each hotel en route.

Southern Tuscany:


Night 1

** Piccolo Hotel Etruria
Small, simple hotel in heart of medieval centre. Room only.

*** Santa Caterina
Converted 18C villa, close to medieval gates of historic centre. B&B
Night 2
*** Borgo Antico
Family-run hotel in hamlet converted from traditional fattoria. B&B

Night 3
** Roma
Simple inn with trattoria in lively little walled town. HB
*** Il Ghibellino
Family-run, new hotel in centre of town. HB
Nights 4 & 5
*** Il Palazzo Toscano
Restored palazzo in town centre. B&B

*** Dei Capitani
Comfortable hotel with superb views, small pool in summer. B&B
Night 6
Bagno Vignoni
** Le Terme
Modern hotel overlooking Roman baths. B&B
Bagno Vignoni
*** Locanda Del Loggiato
Comfortable locanda in small village. B&B
Night 7
*** Residence San Gregorio
Converted theatre, close to centre. B&B.
*** Il Chiostro
Converted monastery in town, with cloisters, pool in summer and views. B&B


Southern Tuscany:



Walking: Open hills with long views. Paths lie mostly along farm tracks, ancient drove roads, forest tracks, and gravel country roads.

Cycling: a mixture of small asphalted country roads and strade bianche (well-surfaced gravel roads). Wonderful views justify cycling uphill.

When to go

Start any day from 01 Apr to 24 Oct



Of interest.
Worth travelling to see if you are in the area.
Of great interest.
Worth travelling to see if you are in the country.
Of outstanding interest.
  Worth travelling to see if you are in Europe.



On Route


***Siena the best preserved great medieval city in Europe. An abundance of outstanding 14C and 15C art and architecture. Also see the Piazza del Campo, scene of the Palio horserace.


* Buonconvento small town on ancient Via Cassia, museum with fine 14-15C Sienese pictures and Art Nouveau features.


* Montalcino superbly-sited medieval town with castle (1361) and Museo Civico with fine Sienese pictures. Enoteche where you can taste (and buy!) the superb Brunello di Montalcino. Nearby is the exquisite 11C church of Sant'Antimo, built of alabaster and onyx.


* Bagno Vignoni Roman thermal baths occupy the village piazza.


** Pienza birthplace of Aeneas Piccolomini, elected Pope Pius II in 1458, who changed the town's name from Corsignano to Pienza by Papal bull and employed Rossellini in 1462 to transform it into a tiny Renaissance 'city'. Palazzo Piccolomini, Duomo and museum. Outside: Pieve di Corsignano, with 6C crypt.


** Montepulciano (optional route continuation) Fine palazzi, cathedral, frescoed churches and museum with Della Robbias as well as the superb Renaissance church of San Biagio.


Flights & Transport

Recommended Destination Airport: Pisa Florence

There are international flights to Pisa and Florence. From Pisa Airport trains run frequently to Siena (change at Empoli), the start of your trip. The airport in Florence is five miles from the train station (airport bus) from where trains run direct to Siena. Return: buses from Pienza connect with trains to Siena, Pisa, Florence etc. Most places on route are connected by public transport, or taxi.


Pisa Airport to the First Hotel - approximately 220 Euros.
Florence Airport to the First Hotel - approximately 155 Euros.
Last Hotel to Pisa Airport - approximately 220 Euros.
Last Hotel to Florence Airport - approximately 170 Euros.


No. of luggage moves included: 5

No. of nights with half board (dinner included): 1

Cycle hire: £60 / $108

Shortest / Longest days walk: 2 hrs 30 / 7 hrs

© 2011 Italian Excursions || terms and conditions