Self-Guided Tuscan Trails - Florence to Siena

Your accommodation for the first two nights of your holiday is conveniently located in the heart of Florence. If you have time after checking-in, we recommend taking a walk around the city's magnificent squares and along the illustrious Arno River. This walk starts and ends in the Piazza della Signoria and takes about three and a half hours.

Widely regarded as the cradle of the Renaissance, Florence is a city which impresses at every turn. From the Duomo Cathedral to the Ponte Vecchio Bridge and Michelangelo's spell-binding statue of David, there is so much to discover. A visit to the Uffizi Gallery is a must, with its abundance of canvases by Botticelli, Leonardo da Vinci and a host of other greats.

Public transport and taxis can be easily organised from both Florence Airport (FLR) and Pisa Airport (PSA) on your arrival. Stay: Hotel Bonifacio (Comfortable)

After a twenty-five minute public bus ride to Settignano, your walk commences from this picturesque hillside village. Along your route, you will pass magnificent cypress trees, olive groves and Renaissance villas, with a view of Florence below you.

Upon your arrival in the charming town of Fiesole, we recommend spending time exploring its Etruscan ruins, Roman amphitheatre and Franciscan monastery. You can either choose to return to Florence by public transport from here, or extend the walk by strolling back to Settignano via another route.

Depending on whether you choose the one-way or circular walk, you can expect today's eight and 16 kilometre walks to take approximately three and six hours, respectively. Stay: Hotel Bonifacio (Comfortable) (B)

After breakfast, you take a private transfer by car to Montespertoli - a rustic market village set in the rolling green hills not far from Florence. Here, you will find your hospitable agritourismo accommodation that will be your base for the next two nights. Once you have settled in, head out for a stroll through the open countryside to the north of the town, with views of vineyards, olive groves and isolated farms perched on hilltops. Later, return to your hotel for a refreshing dip in the pool.

You can expect today's 14 kilometre walk to take approximately four hours. Stay: Hotel Il Molino del Ponte (Comfortable) (B)

Today's circular walk affords another opportunity to enjoy the picture-perfect landscape around Montespertoli. This time you walk south, through the Chianti Fiorentino area, passing by old parish churches and elegant country villas.

You can expect today's 14 kilometre walk to take approximately four hours. Stay: Hotel Il Molino del Ponte (Comfortable) (B)

After breakfast, a short car transfer takes you to the village of Gambassi. From here, you will start your walk along the Via Francigena - a 700 year-old pilgrim route to Rome, which is thought to have originally started in Canterbury, England. The track affords spectacular views of the surrounding countryside and takes you into the centre of the walled Medieval town of San Gimignano - your base for the next two nights.

You can expect today's 17 kilometre walk to take approximately five hours, although the route can be shortened to nine kilometres and three and a half hours, should you wish. Stay: Hotel La Cisterna (Comfortable) (B)

Today, you have the choice between two relatively gentle circular routes around San Gimignano. Both take you along cypress-lined country lanes and past vineyards and fields, taking in the picturesque hamlets of Monteauto and Santa Lucia.

Depending on which route you choose, you can expect today's 10 and 14.5 kilometre walks to take approximately three and four and a half hours, respectively. Stay: Hotel La Cisterna (Comfortable) (B)

After breakfast, take a private transfer to the fortified village of Monteriggioni. From here, your walk takes you to the marvelous city of Siena, famous for its biannual "Palio" horse race, held in the beautiful shell-shaped Piazza del Campo.

The narrow streets of this fantastically-preserved Italian jewel are bursting with imposing Medieval palaces, interesting museums and awe-inspiring churches that are well-worth exploring. During your time here, we particularly recommend a visit to the Duomo, as well as climbing to the top of the bell tower.

You can expect today's 19 kilometre walk to take approximately five hours. Stay: Hotel Chiusarelli (Comfortable) (B)

After breakfast, the organised part of your holiday comes to an end.

Public transport and taxis can be easily organised to both Florence Airport (FLR) and Pisa Airport (PSA). (B)