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Cycle the Wine Regions of Tuscany
Find trips›Italy›Cycle the Wine Regions of Tuscany
UTOperated by UTracks

Cycle the Wine Regions of Tuscany

From
CAD 2,290
Duration
8 days
Countries
Italy
Activity
moderate

The adventure

Experience the magic of cycling in Tuscany on this 8-day tour. Quality hotels & agriturismo, GPX tracks, bike hire & 24/7 support team. Popular self-guided cycling holiday in Italy.

At a glance

Duration
8 days
Route
→
Countries
Italy
Activity level
moderate
Style
Cycling, Food & Drink
Group size
Ask
Flights
Not included
Solo travellers
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Day by day

View of a historic hilltop town surrounded by lush greenery under cloudy skies.
Your journey through

Italy

Showing Days 1-7

8-day itinerary

Day 1Day 1: Arrive BuonconventoYou will be collected from Buonconvento train station and dropped off at Pieve a Salti (this is included and you must contact your accommodation in advance to inform them of your arrival time). For your 3 nights, you will be staying at an organic farmhouse (agriturismo) nestled amidst the magnificent rolling countryside of the Crete hills south of Siena. This large Tuscan estate produces olive oil, organic cereals and pasta that are used to prepare the typical regional dishes you will enjoy at their restaurant.
You will be collected from Buonconvento train station and dropped off at Pieve a Salti (this is included and you must contact your accommodation in advance to inform them of your arrival time). For your 3 nights, you will be staying at an organic farmhouse (agriturismo) nestled amidst the magnificent rolling countryside of the Crete hills south of Siena. This large Tuscan estate produces olive oil, organic cereals and pasta that are used to prepare the typical regional dishes you will enjoy at their restaurant.
Day 2Day 2: Circular ride to Murlo & Le Befa (33km/20.5mi)A great first ride through the countryside on well kept dirt roads to Murlo. Immerse yourself in the dense woods as you ride by the Crevole River. Continue past steep cliffs to the sweet smell of bright yellow flowers and through an enchanting oak tree forest to La Befa. A short part of the trail is too narrow or rocky to cycle (about 300m) however the exhilarating views are more than worth the effort. Return to Buonconvento. Ascent: 402m / Descent: 483m
A great first ride through the countryside on well kept dirt roads to Murlo. Immerse yourself in the dense woods as you ride by the Crevole River. Continue past steep cliffs to the sweet smell of bright yellow flowers and through an enchanting oak tree forest to La Befa. A short part of the trail is too narrow or rocky to cycle (about 300m) however the exhilarating views are more than worth the effort. Return to Buonconvento. Ascent: 402m / Descent: 483m
Day 3Day 3: Circular ride to Montalcino (24.1 or 42.6km/, 14.9 or 26.4mi)Pedal through vibrant fields of sunflowers past Buonconvento to the heart of the Brunello wine district. The Monte Amiata volcano lures above as the surrounding countryside transforms into endless olive groves and vineyards. Ride steeply up to the fortified city of Montalcino where you can visit its magnificent 14th century fortress and Palazzo Comunale, then return to Buonconvento along remote back roads. Ascent: 654m / Descent: 735m
Pedal through vibrant fields of sunflowers past Buonconvento to the heart of the Brunello wine district. The Monte Amiata volcano lures above as the surrounding countryside transforms into endless olive groves and vineyards. Ride steeply up to the fortified city of Montalcino where you can visit its magnificent 14th century fortress and Palazzo Comunale, then return to Buonconvento along remote back roads. Ascent: 654m / Descent: 735m
Day 4Day 4: Cycle to Pienza (37.7km/23.4mi)Climb uphill to the renowned monastery of Monte Oliveto Maggiore with its delightful frescos and botanical garden. After replenishing your soul, follow a winding route past isolated villages until you reach a row of hundreds of cypress trees, inviting you to visit the stunning Sant’Anna in Camprena monastery. Admire the frescos then finish your day in the lovely town of Pienza where you will be spending your next 3 nights. Ascent: 714m / Descent: 638m
Climb uphill to the renowned monastery of Monte Oliveto Maggiore with its delightful frescos and botanical garden. After replenishing your soul, follow a winding route past isolated villages until you reach a row of hundreds of cypress trees, inviting you to visit the stunning Sant’Anna in Camprena monastery. Admire the frescos then finish your day in the lovely town of Pienza where you will be spending your next 3 nights. Ascent: 714m / Descent: 638m
Day 5Day 5: Loop cycle to Bagno Vignoni (27.7km/17.2mi)Today is a relaxing day in which you will travel on smooth country roads to the medieval hamlet of Bagno Vignoni where you can rest and swim in its healing thermal waters, enjoyed by the Romans and home to the legendary water nymphs. Ride back to Pienza along gently undulating hills through unspoiled countryside embracing the essence of Southern Tuscany. Ascent: 504m / Descent: 503m
Today is a relaxing day in which you will travel on smooth country roads to the medieval hamlet of Bagno Vignoni where you can rest and swim in its healing thermal waters, enjoyed by the Romans and home to the legendary water nymphs. Ride back to Pienza along gently undulating hills through unspoiled countryside embracing the essence of Southern Tuscany. Ascent: 504m / Descent: 503m
Day 6Day 6: Circular route to Montepulciano (34km/21mi)From Pienza, travel along immensely panoramic roads past the medieval stone-built hamlet of Monticchiello. Ride up a remarkable limestone ridge and enjoy breath-taking views of the Val d’Orcia. Gather your strength as you make the climb up to Montepulciano. Upon arrival, celebrate with a glass of the famous local Vino Nobile wine before freewheeling back to Pienza. Ascent: 739m / Descent: 751m
From Pienza, travel along immensely panoramic roads past the medieval stone-built hamlet of Monticchiello. Ride up a remarkable limestone ridge and enjoy breath-taking views of the Val d’Orcia. Gather your strength as you make the climb up to Montepulciano. Upon arrival, celebrate with a glass of the famous local Vino Nobile wine before freewheeling back to Pienza. Ascent: 739m / Descent: 751m
Day 7Day 7: Cycle to Pieve a Slati via Lucignano d'asso (24km/15mi)The ride today is mostly on gravel road, gentle rolling hills in the most beautiful countryside of the Orcia valley. Half way you can stop in Lucignano d'Asso, a tiny village on the L'eroica cycle route. Then you ride back to the organic farm of Pieve a Salti where you spend your last evening (restaurant is 1km from accommodation - they provide shuttle service to/from the restaurant). Ascent: 266m / Descent: 528m
The ride today is mostly on gravel road, gentle rolling hills in the most beautiful countryside of the Orcia valley. Half way you can stop in Lucignano d'Asso, a tiny village on the L'eroica cycle route. Then you ride back to the organic farm of Pieve a Salti where you spend your last evening (restaurant is 1km from accommodation - they provide shuttle service to/from the restaurant). Ascent: 266m / Descent: 528m
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Discover Italy

A glimpse of the destination you'll explore.

Picturesque landscape of Lake Garda with a distant island under a summer sky.
Overcast day in Tuscan hills featuring cypress trees and traditional stone house.
A picturesque town nestled by cliffs on the Amalfi Coast, Italy.
Picturesque view of Tuscany's rolling hills, vineyards, and Italian villas under a clear summer sky.
Beautiful view of Ponte Sant'Angelo spanning the Tiber River in Rome, Italy under a clear sky.

Upcoming departures

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3 Aug – 10 Aug 2026(price may vary)
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UT
Operated by UTracks

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Aug 3, 2026CAD 2,290 · available
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