11 Day Tour

Day 1

Arrive at Pisa airport. Transfer by minibus or taxi to our base hotel in Pienza.

Day 2

Pienza. After breakfast you’ll be equipped with your bicycle. The day is then yours to explore Pienza, a perfect example of a Renaissance town commissioned by Pope Pius II in 1459. This UNESCO World Heritage site is set amid idyllic Tuscan scenery of cypress trees, olive groves, sunflowers and vineyards.

Day 3

Pienza to San Giovanni d’Asso: 18 miles (29km). A relaxing day spent meandering through sleepy backwaters. Much of the route follows Strade Bianche, the tranquil back-roads that criss-cross Tuscany. A 13th century castle lies at the centre of San Giovanni d’Asso, part of which has been converted into a boutique luxury hotel and restaurant; your stay here should prove a special treat.

Day 4 

San Giovanni d’Asso. This charming village lies at the heart of the Crete Senesi, a region of clay hills southeast of Siena. Renowned for its truffles, the village is actually home to the world’s only truffle museum! Quiet byways link the peaceful villages here - an excellent opportunity to explore this undiscovered corner of Tuscany.

Day 5

San Giovanni d’Asso to Castelnuovo Berardenga: 24 miles (38km). The tour continues north passing through Asciano, an atmospheric ancient town with evidence of 5th century Etruscan settlers. Beyond Asciano a remote lane rolls across the Crete Senesi emerging at Castelnuovo Berardenga, a picturesque village on the southern fringe of Chianti.

Day 6 

Castelnuovo Berardenga. The enchanting heart of Chianti lies to the north of Castelnuovo Berardenga, a landscape of undulating hills adorned with vineyards and forests. We suggest a route visiting some of the pretty wine centres in the south of the region.

Day 7 

Castelnuovo Berardenga to Castellina in Chianti: 24 miles (38km). A glorious ride through vineyards and olive groves passing Chianti’s legendary winemakers. Of course, there’ll be opportunities to sample and purchase a few bottles (our representative will collect your purchases). The intoxicating scenery is a pure delight of hilltop villages, avenues of cypress trees, and golden fields of sunflowers.

Day 8

Castellina in Chianti. The medieval village of Castellina in Chianti is endlessly fascinating - from the imposing Rocca (castle) with its huge 14th century tower and small Etruscan museum, to the Via delle Volte, an underground tunnel skirting the town wall which serves as a vast wine cellar. The nearby village of Radda in Chianti has a charming main street lined with historic buildings and is a producer of excellent wines. The breathtaking views on our suggested loop are truly inspirational.

Day 9 

Castellina in Chianti to San Gimignano: 24 miles (38km). Today’s ride begins with a long winding descent towards the Siena Plains. After crossing the Val d’Elsa, the route continues through classic rolling Tuscan landscapes.

Day 10

San Gimignano. Renowned as the ‘city of beautiful towers’, San Gimignano is among the best preserved medieval towns in Tuscany. With 14 towers dating from the 13th century creating a stunning skyline, the town is best explored on foot - discover its excellent museums, restaurants and shops that line the historic cobbled streets. Of course, we also suggest a last gentle pedal to soak up the unique beauty of the Tuscan countryside.

Day 11

We say “Arrivederci” before transferring you direct from San Gimignano to Pisa airport by train or minibus.

One Night Or Two?

Most of our holidays are available in two formats: BSpoke Original (two-night stays at each hotel, moving on alternate days), and BSpoke One Night Stops (two nights in your first hotel, followed by just one night in each subsequent hotel, for those who want to cycle a distance every day).