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Walk from unspoilt hill-top San Gimignano to Siena, the best-preserved great medieval city in Europe • Timeless countryside, as seen in the background of medieval paintings • Hills crowned with medieval cities and villages – San Gimignano, Colle Val d’Elsa and Monteriggioni • Patchwork of vineyards and olive groves, ancient forests, fields of wheat and barley • Ancient festivals and traditions preserved in the towns and villages
Tuscany & Siena: Itinerary

Day 1 Arrive in San Gimignano

Day 2 Free day in San Gimignano Option circular walk


Day 3 San Gimignano to Colle Val d`Elsa
Walk through forest and over the hills with views over an almost unchanged medieval landscape to Colle Val d`Elsa (8.5 miles,4.5hrs)


Day 4 Colle Val d`Elsa to Monteriggioni
Walk to Monteriggion across an undulating fertile area of small farms via fine Ramanesque abbey church (11.3miles, 6hrs)


Day 5 Monteriggioni to Siena
Through forests, past two castles, open farmland and more woods. Wonderful views of Siena (11.3 miles, 65hrs)


Day 6 Free day in Siena
Optional Siena city walk (3.5 hrs)


Day 7 Departure day
Why not extend in Siena ,Florence or at Pieve a Castello?



Shorter 5 day Itinerary

One night in each hotel en route.


Tuscany & Siena:


Nights 1 & 2
San Gimignano
*** Leon Bianco
Comfortable hotel in medieval centre. B&B

Night 3
Colle Val d'Elsa
*** Arnolfo
Palazzo converted in 1960s in medieval Colle Alto (high town). simple rooms. B&B.

Night 4
Il Castello
Rooms in converted house within village walls. Room Only.
Nights 5 & 6
** Piccolo Hotel Etruria
Small, simple hotel in heart of medieval city centre. Room only
Tuscany & Siena:



Walking: Hilly countryside is crossed by strade bianche (small gravel roads), mule tracks, farm and wood-land tracks and paths, with some asphalt on the approach to towns, notably Siena.


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


* Certaldo: unspoilt medieval hill town with massive 12C pink brick ramparts. Boccaccio, author of the Decameron, lived here, and his house is now a museum.


** San Gimignano: walled medieval town with world famous towers. Romanesque Collegiata, with very fine frescoes by Bartolo di Fredi, Taddeo di Bartolo, Benozzo Gozzoli and others. Palazzo del Popolo with picture gallery. Church of Sant' Agostino, with frescoed choir and fine high alter.


* Colle Val d'Elsa: walled town with perfectly preserved medieval 'tunnel' streets.


*** Siena: Piazza del Campo, scene of the Palio. Palazzo Pubblico with pictures and frescoes including the Lorenzetti Good & Bad Government. Medieval Duomo (built 1196-1216) of black and white marble, with remarkable Libreria Piccolomini, decorated by Pinturicchio. Museo dell' Opera with Duccio's Maesta. Pinacoteca: the most important picture gallery for study of Sienese masters - the list goes on and on...


* Monteriggioni: Tiny medieval village encircled by 13C walls surmounted by watchtowers.


The Palio pageant and horse race round the Campo of Siena takes place on 2 July and 16 August.


Flights & Transport

Recommended Destination Airport: Pisa Florence

There are frequent international flights to Pisa and Florence. From Pisa airport trains run regularly (change at Empoli) to Certaldo and Siena, connecting you with the beginning and end of your trip. The airport in Florence is 5 miles from the train station (airport shuttle bus) from where trains run to Certaldo (via Empoli) and Siena. Each place on route is connected by public transport.

Public transport on route

Pisa airport to First Hotel - approximately 100 Euros.
Florence airport to First Hotel - approximately 90 Euros.


No. of nights with half board (dinner included): 0


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