Walkers' World 
Guided Rambling Holidays in
Southern Tuscany    


Itinerary:

Saturday: Pick up at Florence Santa Maria Novella Rail Station at 4.00 pm. Transfer by bus to our hotel near Siena (about 90 minutes through beautiful countryside). This evening before dinner we have a welcome drink and get-together for the guides to describe the next day's walk.

Sunday:  In the morning we travel a short distance by private bus to the start of our walk.
This is one of the most stunning sections of the medieval pilgrimage trail that led from Northern Italy to Rome.  Soon we reach Abbadia Isola, a monastery surrounded by a tiny village dating back to the 10th century when it was an important resting place for pilgrims and travellers on their way to Rome.  We continue on through beautiful countryside filed with olive orchards and wheat fields.  Our mid-day goal is the perfectly preserved walled medieval castle/village of Monteriggioni which has stood atop a low hill since 1200.  On reaching the town there is time to explore its narrow cobblestoned streets, relax over a gelato, visit the museum or walk atop the castle walls. Our walk then continues to the outskirts of Siena in time for a dip in the pool or perhaps a drink on the vine-covered terrace.

Short walk 5 km   total climb 150 m + 80 m   Long walk 12.5 km   total climb 330 m + 370 m

Monday: Today we transfer by private bus to begin a walk from the exquisite town of Pienza. Pienza  has changed little since it was built in the 15th century as a project of Pope Pius II.  A native of this region, the pontiff’s dream was to create an “ ideal”  town. Construction started but war intervened and funds ran out so the jewel of a town now sits as if frozen in time.
We  walk through the lovely Val D’Orcia (a UNESCO World Heritage site) to the town of  San Quirico and along the way picnic near the Chapel of Vitaleta.  After exploring San Quirico there is an option of continuing on foot to Bagno Vignoni or by bus.  At Bagno Vignoni we see the ancient Roman baths fed by warm springs. In the 1400's Medici princes frequented these hot pools for medicinal reasons.  It is possible to have a dip in one of the thermal pools before we return to Siena.

Tuesday:  Morning transfer by private bus to a small Tuscan village where we begin our walk to the exquisite town of San Gimignano. We ramble along quiet country roads amid vineyards and beautiful Tuscan scenery with the fragrance of wild fennel and rosemary pervading the air. Soon the medieval spires of San Gimignano can be seen in the distance. In medieval times San Gimignano was the Manhattan of its time with each wealthy family competing to build a taller tower. Some of the spires were for defence but some were just for the sake of egos. Our route is easy walking but with an uphill entrance to the town at the end.  San Gimignano is a treasure-trove of museums, churches, Renaissance art and 14 original medieval towers. But, even more important, there is an abundance of gellaterias selling mouth-watering ice-cream.

Wednesday:  This is market day in Siena. The town is centred around a magnificent black and white marble Duomo (cathedral) and around the famous Campo where everything used to happen from banquets to bartering, from hangings to horse-racing. This jewel of a town offers art treasures, Renaissance palaces, a Medici fortress, great artistic masterpieces, and a maze of narrow alleyways filled with shops offering scrumptious local delicacies. There is also the Enoteca for wine tasting. The morning is free to explore the market and in the afternoon we have a guided walking tour.

 In the evening there may be an optional opera concert in an atmospheric old church converted to an auditorium in the centre of Siena.
  Here you can enjoy well-known, spine-tingling arias from Italian operas sung by local artists.  These concerts stopped during the pandemic but hopefully will start again in 2022. In 2019 tickets cost 20 euros.

Short walk 7 km   total climb 270m +160 m   Long walk   11 km   total climb 480 m + 230 m

Thursday: Today we stroll on country footpaths to visit the Etruscan archaeological dig at Poggio Civitate where many interesting Etruscan artefacts have been unearthed. The walk continues on through a woodland trail to a remote monastery with spectacular views. We picnic here and then our bus takes us a short distance and we continue the walk to the Abbey of Monte Oliveto Maggiore. This exquisite old structure is filled with fascinating frescoes by the famous Renaissance artists Luca Signorelli  and Giovanni Bazzi  depicting the life of St Benedict. The monastery was built in this remote location by the wealthy elite (males) of Florence who wanted to escape to a spiritual life away from the city in the early 1400’s.  (Perhaps escaping plague or violent wars added to their motivation.)  Today it is still a working monastery with a shop selling herbal remedies and home-brewed liqueurs.

Morning walk 7 km   total climb 180m + 300m  Optional afternoon walk  7 km  220m +260 m

Friday: Today we travel a short distance north by private bus to the small fortified and walled village of San Gusme in the Chianti region. From here we do a loop walk through lovely Chianti countryside and then continue to the impressive Castello di Brolio, a medieval castle surrounded by a Chianti wine estate with vineyards and Renaissance gardens.  Here there is a choice of doing a loop walk or visiting the gardens and castle.  The entry to the gardens includes a wine-tasting of Chianti wines produced here.

Morning walk 7 km   total climb 190m   optional walk 5 km total climb 120m

Saturday: Return by private bus to Florence Rail Station about 11.00 am.

     

Southern Tuscany

Where we Stay

Itinerary

Contact us and Booking

Cost and Details

Terrain and Level of Difficulty

Frequently Asked Questions

Walkers World Homepage