After arriving in Pisa, your guides will drive you through the beautiful Tuscan Landscape, arriving at the first accommodation set in the outskirts of the famous town—in the countryside of San Gimignano. You’ll stay in a stunning agriturismo, where your host will prepare your first Tuscan dinner. With a plunge in the pool overlooking the vineyards, your holiday can officially start!

Driving: 90 minutes
Meals: Dinner

Set off the day with a fun off-road section into the valley before looping back towards San Gimignano. Journey south following a mix of dirt roads and trails through woods, over hills and crossing streams, through a constantly changing rolling Tuscan landscape. Most climbs will be on farm or forest gravel routes, which lead onto sections through vineyards and fields, trails and paths used mostly by local people and farmers. Your destination for today is Strove, a small hamlet not far from Abbadia Isola and Monteriggioni. After stopping in the square for a well-deserved beer, reach your accommodation, where you can enjoy a dip in the pool before heading out for dinner.

Distance: 22 miles / 35 km
Ascent: 600 m
Meals: Breakfast, lunch

Your first stop for today is the quaint medieval hamlet of Monteriggioni, with time to explore the castle walls and narrow streets. Leaving the fortified village, you’ll continue with a steady off-road climb through the Montagnola range, an area well known for the Gran Fondo Sienese MTB race. Explore the network of dirt tracks leading into the hillside forests, looping on fun rolling singletracks towards little hamlets and twisting down over rolling fields. A final fun section of singletrack winding through forests will lead you to the outskirts of Siena. Spend some time wandering through the town and visit the Palio Square and Duomo, before heading out to dinner.

Distance: 22 miles / 35 km
Ascent: 750 m
Meals: Breakfast, lunch  

Leave Siena and continue your journey south on the Eroica route and into the Crete Senesi. Arriving near the ancient Etruscan hamlet of Murlo, enjoy a fun ride on narrow trails by the Crevole River and up a former mining railway track. Head to Buonconvento, where you’ll stop for a refreshing break and, if inclined, visit the fortified walls. Your accommodation is right in the center of town, so enjoy some downtime and join the locals for aperitivo!

Distance: 28 miles / 45 km
Ascent: 500 m
Meals: Breakfast, dinner  

Your mountain bike pilgrimage continues! Head towards Pienza, right in the heart of the UNESCO heritage site of Valle d‘Orcia. The route takes you along the ridge lines, offering 360 degree views. The trails are a mix of farm tracks and dirt roads, with steep sections which will get you out of the saddle. Today is a tougher day in terms of ascent, and after joining a section of the Eroica, you’ll reach your accommodation in the heart of Pienza– the perfect base for two nights allowing you to explore some cultural and historical sites as well as small Tuscan shops, wine bars and restaurants.

Distance: 26 miles / 42 km
Ascent: 1000 m
Meals: Breakfast, lunch  

Your group can choose between different options for today’s ride depending on the preferred terrain—all the trails lead to San Quirico d‘Orcia. Descend quite steadily on a fast gravel track into the Orcia valley and loop back through fields, dense woods and past castle hamlets, until you reach the medieval hamlet of Bagno Vignoni with its healing baths and home to the legendary water nymphs. After resting, head to the center of Valle D‘Orcia and start a steady climb towards Pienza. Absorb and visit the local sites before indulging in another delicious Tuscan meal at one of the carefully selected local restaurants.

Distance: 25 miles / 40 km
Ascent: 900 m
Meals: Breakfast

After breakfast, your guides will take you back to Pisa to say your farewells and savor the memories of a fantastic week on your bike!

Driving: 2h 45min
Meals: Breakfast