Secrets of San Gimignano Cycling

Arrive in Volterra where you've time for a dip in the pool and a wander round
its myriad of cobbled alleys and hidden squares before dinner. *(Staying at
Park Hotel Le Fonti)*

Day 2

*/Option: 1/*

Today it's a downhill whizz out of hilltop Volterra and into the pretty Era
Valley where spectacular views of the surrounding timeless Tuscan countryside
open up as you pedal. After climbing out of the valley, you'll soon pass
through the pretty hamlet of Castagno where we suggest a well-deserved coffee
stop in the local bar. Your route continues on to Gambassi Terme, a
well-preserved spa town with cobbled streets, 12th century church and lovely
shaded gardens. Lunch here perhaps in one of the many trattorie then, soon
after leaving the town, you'll pick up the famous Via Francigena for the
gentle, mainly downhill stretch to mediaeval Certaldo where you can stop for
a gelato before your final climb through olive groves and vineyards to the
hamlet of Pancole. *(Staying at Hotel Certaldo)*

 

*/Option: 2
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/*Distance - 75.4km (elevation +1036m / -1238m)* /

Leaving Volterra you drop down into the valley heading north passing the
Theatre of Silence and the family home of Andrea Bocceli. Ride past rich
green meadows, before climbing through the stunning countryside and on to the
pretty spa town of Gambassi Terme. A long downhill ride lets you roll into
Certaldo before a short climb to the peaceful Hotel Le Renaie for the next
two nights.

 

Day 3

If you fancy a day off from cycling, the pool here is simply gorgeous and
nice lunches are served on the geranium-scented terrace. There's also a small
shop where you can buy olive oils, produced by the owners, and Tuscan wines.
The more energetic might want to cycle past orchards and vines to visit
Boccaccio's birthplace, stunning Certaldo. Take the funicular to its medieval
centre for spectacular views across the Val d'Elsa. *(Staying at Hotel
Certaldo)*

Day 4

 

*/Option: 1/*

Today's route explores the panoramic wine country between Pancole and Colle
di Val d'Elsa. You'll first retrace your route to Certaldo and then follow
the official, mainly off-road, Chianti Wine Route where you'll find lots of
tasting opportunities - don't forget, we can collect any purchases for you!
It's then on to the old town of Poggibonsi, a perfect stop for lunch and to
visit the ruins of its unfinished 15th century fortress. The day ends with
gentle pedalling through tree-lined meadows and a valley of poppy and
sunflower fields to Colle di Val d'Elsa. *(Staying at Relais Della Rovere)*

 

*/Option: 2/*

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/*Distance - 91.9km, elevation: +1521m / -1616m*/

Today you head into wine country on a beautiful ride with vines as far as the
eye can see and passing through beautiful hamlets and interesting wine towns.
With the climbing over you pass two of the famous Chianti towns, Castellina
and Radda, both offering great wine tasting chances and good restaurants.
Heading down to the valley you pass the stunning walled village of
Monteriggioni before heading on to Colle Val d’Elsa for your next two
nights.

 

Day 5

There's masses of choice today: explore the mediaeval old town which dates
back to Etruscan times; take the bus to Siena (30 mins) or to Florence (60
mins); take in the mediaeval town of Monteriggioni, an easy cycle or short
bus ride away; or simply laze by your hotel's sparkling swimming pool,
surrounded by lovely gardens. *(Staying at Relais Della Rovere)*

Day 6

 

*/Option: 1/*

It's easy pedalling this morning as you head south past the old town of Colle
di Val d'Elsa, gradually climbing up to Casole d'Elsa, a beautiful village
characterised by ancient vermilion-hued buildings and blessed with stunning
views from its hilltop position. Take time to explore its 12th century church
(frescoes by Gano da Siena) and impressive fortress before an early lunch
perhaps, in the lovely piazza. You then wind north, gently uphill, through
wonderfully scenic countryside against the backdrop of the impressive
mediaeval towers of San Gimignano as you pedal on to Pescille. *(Staying at
Hotel Pescille, Breakfast at the hotel)*

 

*/Option: 2/*

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/*Distance - 87.4km, elevation: +1693m / -1542m*/

Heading to the south of the region today you are rewarded with beautiful
scenery, quiet roads with vistas of mountains and hills as you pass pleasant
meadows, small forests and lines of cyprus trees. You pass small villages and
towns that are well off the beaten track. Maybe take a late lunch in walled
Casole d’ Elsa, then pass Castel San Gimignano and finish through the vines
to Hotel Pescille for the next two nights.

Day 7

San Gimignano is just a short cycle away; explore its myriad of narrow
streets and many hidden cobbled squares before returning to your tranquil
hotel for a refreshing dip in the sparkling swimming pool. *(Staying at
Hotel Pescille)*

Day 8

*/Option: 1/*

It's a short ride to San Gimignano today before a climb up through classic
Tuscan landscapes of vines, olive groves and fields ablaze with sunflowers.
Enjoy the 16km, mainly downhill run into the Era Valley. There's a real sense
of achievement on your final climb through open countryside and you'll enjoy
spectacular views before heading back to the ancient cobbled streets of
Volterra. *(Staying at Park Hotel Le Fonti)*

 

*/Option: 2/*

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/*Distance - 59.4km, elevation: +1078m / -943m*/

From the hotel you head towards San Gimignano, circling the 'town of towers'
for 360 degree views and passing through the surrounding wine country. Head
uphill through the vineyards and then enjoy a long downhill route with views
of Volterra. Finishing with a climb into Volterra, pass through the town and
ride back to your hotel for the last night.

Day 9

LEAVE VOLTERRA