Treasures of Central Tuscany

Day 1

San Gimignano township & welcome dinner provided
2 hours stroll with a guide

After settling into your accommodation, the afternoon is free to explore the town together. Take time to look up at the ancient iron hardware holding the buildings together, view birds wheeling and nesting, search for the ancient protected trees or lean over the Piazza della Cisterna and feel the groves left by ropes bringing up water.

Day 2

San Donato Loop
4 hours easy to moderate
Picnic lunch provided

Our walk takes us through the 13th century Porta San Giovanni and enters a lush, fertile valley with prosperous farming on either side. As we leave the valley, our path becomes an ancient stony cart track. We then emerge from woods onto a paved road leading uphill into the tiny village of Racciono, sitting high on a ridge. We continue on a broader, busier road to the pretty hamlet of San Donato. Here we have spectacular views back to San Gimignano.

Walking on through a rich farming valley, we reach a huge, ancient oak. The path then follows alongside vines and olive trees before reaching the road to Montauto.

After stopping to enjoy the views, we wind our way down to cross the Borroimboltroni River passing an old mill, now restored as a private home. Old terracing with olive trees accompanies us until we reach the road back to San Gimignano. This final stretch is a mixture of the old, including the Mount Oliveto convent, and the new San Gimignano.

San Gimignano Loop
2.5 - 3.0 hours easy undulating
El fresco dinner provided

Our walk leaves by the Porta San Matteo and follows a short section of local road before we leave it to enjoy the traditional Tuscan countryside. Very rarely are stunning views of San Gimignano and its fabulous towers not able to be seen on the horizon. Our route takes us along cart ways, through rich agricultural farming including vines, olives, hay making, figs and walnuts. On returning via the Porta San Giovanni, we will have an imposing view of the tall tower Plazza de Popolo.

1.5 hours easy strolling
After a free afternoon we will meet at 5:00pm for a stroll around the town's 13th century walls. At Porta San Jacopo we will take a short detour to visit the medieval public water fountain known as Fonti Medievali. Our walk finishes immediately behind our guesthouse at the Rocca di Montestaffoi fort.

Monteriggioni Ring Walk
4 hours easy to moderate, including long gently graded hill
Picnic lunch provided

Monteriggioni is a charming fortified medieval village. It has perfectly preserved walls which date from the 13th century with fourteen towers which were added in 1260. Great views of the Tuscan countryside can be seen from its walls

A local bus takes us from San Gimignano to start our walk. Our track takes us leisurely up through woods to reach a beautiful stone path dating back to Medieval times. Walking along this path your mind wanders back to the people who have passed this way for centuries.

Our path then winds down to cultivated fields and a track leading through fertile farming flats. You catch views of Abbadia a Isola, a Cistercian abbey founded in 1001 on the Via Francigena (the medieval pilgrims way from France to Rome). The abbey was given its name due to its position in the middle of marsh lands. In the 14th century it was fortified by the Sienese and rebuilt in the 18th century.

After exploring the abbey we gradually begin a steady climb on a broad gravel road lined with an ancient stone fence that protects vineyards and olive groves. Towards the top we pass a moving monument to the partisan martyrs of Val D'Elsa. Behind a stone wall are the graves of two partisans gunned down by the Fascists while sleeping.

Our path slowly winds down through pretty shaded woods, allowing the occasional glimpse of Monteriggioni and its towers. On our return there is time to explore this hilltop fortification and walk the walls to enjoy panoramic views.

Loop walk via Ulignano
4 hours easy to moderate
Picnic lunch provided

A rural walk along farm lanes, though woods and vineyards. In spring, wild flowers abound and in autumn, the bouquet of grapes is rich. This is the centre of the San Gimignano wine district, famous for Vernaccia and Sangiovese varieties of wine. We walk by the cellars of wine makers Terruzzi and Puthod and enter some woods before making our way towards the village of Ulignano. After a picnic lunch, our walk passes a highly protected truffle reserve. Great views are on offer back to Castle Ulignano.

Following the pilgrims' route to Certaldo Moderate with short steep sections
4.5 - 5 hours
Farewell dinner provided

Our walk leaves San Gimignano following a section of the ancient Francigena pilgrim road. Our destination is the hill town of Certaldo which is visible for much of our walk along the Val d'Elsa. From the Porta San Matteo our first leg wends though modern day San Gimignano. We soon join the rural cart way passing through Fattoria di Fugnano, one of the region's largest vineyards. The path continues through a forest passing the restored castle Torre di Collemucioli. We join the Pancole Road and soon pass under the archway of the Santuario de Pancole. Built in 1670 and rebuilt after WW2. Along the way we will stop for a well earned rest and picnic lunch.

At this point we leave the Via Francigena pilgrim trail at Piazzetta and climb past the magnificent estate of Villa del Mont. We slowly descend into modern Certaldo prior to catching the funicular to medieval Certaldo. This tiny, pretty hill town is not to be missed even if it's just to admire the mellow brick that it is built in. After some free time to explore Certaldo, having a coffee or just enjoying the views, our return will be via train and bus.

Bus to Florence and on to points beyond