Biking with Leonardo offers a range of biking tours to suit different experience levels and requirements. Our biking club organises guided cycling tours in the following areas:
Please visit our Chianti Tours page for information about our tours in this famous wine region.
Read our testimonials to see why Biking with Leonardo is a top choice for cycling sightseeing and iconic bike rides in Tuscany.
This is a beautiful, fairly gentle route with one steep climb on the ascent to Civitella, which has a handsome castle and ramparts, great coffee and incredible views across the Val di Chiana. We’ll start at Monte San Savino and head to San Pancrazio, a small village close to the edge of Chianti. On the descent, you’ll see the variety of the local landscapes as we pass through olive groves before reaching rolling hills that lead to the approach to Civitella. The village is a little-known gem with a rich history – you can still see bullet holes in the wall of its main church from the German occupation. After we’ve visited the village, we can return on a gravel road with handsome views of the wild countryside and the village of Oliveto, or take a gorgeous long descent to Monte San Savino.
Total distance: 52 km
Total ascent: 700 m
The stunning route on this guided cycling tour is used to train Italian cycling champions and is among the most beautiful rides in the region. We’ll start in Monte San Savino and head towards Siena, passing the castle of Gargonza and Palazzuolo, a hamlet at the top of the hill. The climb is steep but gradual, and the long descent has some of the best views in the region of Val di Chiana and, in the distance, Siena. If we’re lucky, we’ll see some wild boar ambling in the surrounding olive groves. After Colonna del Grillo, we’ll head towards Pietraviva, a tiny village where time has stood still, for great coffee and homemade cake, before another climb to San Pancrazio and a beautiful long descent into Monte San Savino.
Total distance: 55 km
Total ascent: 650 m
This is an iconic bike ride and the first Leonardo taught six years ago when his adventure as a cycling guide began. We’ll start from Monte San Savino and bike along the river Esse towards Foiano della Chiana, the first of many villages we’ll pass through in the Val di Chiana. Renowned for its white truffle market, it’s a lovely place to stop for some great coffee before we head towards Cortona, one of the most beautiful towns in the province of Arezzo, for some cycling sightseeing. Made famous in the film Under the Tuscan Sun, it’s perched on the top of a hill – the ride up is steep and exacting and has breathtaking views of the Tuscan countryside, with vineyards, olive groves and fields as far as the eye can see. The town is gorgeous, with a stunning Cathedral and untouched cobbled streets. After lunch in the main square, we’ll enjoy a long descent from Cortona and take a different route back to Monte San Savino across the Val di Chiana.
Total distance: 73 km
Total ascent: 803 m
Tuscany’s white roads are incredible. Made famous through the Strade Bianche cycling race, they are ideal for biking tours. Alone in the most beautiful countryside in the world, you’ll see panoramic views of rolling hills, cypresses and medieval hilltop towns. This ride to the Crete Senesi (or the clays of Siena) starts at Monte San Savino or Colonna del Grillo (if you want to shorten the ride by 20 km each way) – our biking club caters to any preference. We’ll head towards one of the most famous climbs in the region, the Monte Sante Marie, where we’ll find ourselves in the midst of the Crete Senesi, an area of barren, lunar landscape, gentle hills, solitary cypresses and isolated farms. The tour takes us through stunning and wild landscapes that defy description as we loop through seemingly deserted hamlets before returning on the white roads to Colonna del Grillo.
Total distance: 55 km (if we drive to Colonna del Grillo) or 95 km (without car)
Total ascent: 840 m
One of the most famous amateur cycling races in Italy is the Eroica, a renowned event traversing the white roads of the Val d’Orcia with vintage bicycles. The full race itinerary spans over 200 km, but we’ll tackle only part of the ride covering 78 km. We'll start at Asciano, a charming village in the province of Siena, rich in history and surrounded by rolling hills. From here, we’ll head for the white roads. The landscape is amazing as we cycle through the heart of the Val d’Orcia, a UNESCO World Heritage site known for its stunning scenery. Our route will take us towards a long climb at Castiglion Del Bosco before descending to Montalcino, famous for its delicious wine. After a well-deserved stop to visit the town and enjoy a coffee, we’ll head towards Buonconvento, a hidden gem in the middle of the Val d’Orcia, where we’ll have a lunch break before heading back to Asciano.
Total distance: 78 km (if we drive to Colonna del Grillo) or 118 km (without car)
Total ascent: 1300 m
This is a wonderful ride to Pienza, one of the most beautiful hill towns in Tuscany, nestled in the heart of the Val d’Orcia. The landscape is very different to Chianti – wide, expansive views, rolling hills, cypresses and medieval hilltop towns and castles. Biking tours can start in Monte San Savino or Serre di Rapolano (if you want to shorten the ride by 50 km). We’ll cycle to Trequanda and Madonnino, two handsome hill towns, passing across Tuscan plains where every curve and ascent offers breathtaking vistas of vineyards, olive groves and fields of golden wheat. With their narrow streets and welcoming squares, these towns offer an authentic taste of Tuscan life. We’ll reach Pienza for lunch where we can taste its famous Pecorino cheese and explore the town’s gorgeous Renaissance church, handsome piazza and incredible views. The route back is quite long, but the climbs are moderate, and the colours and beauty of the landscape are extraordinary.
Total distance: 73 km (if we drive to Serre Di Rapolano) or 123 km (without car)
Total ascent: 1500 m
This is a magical ride that takes you across the empty plains of Val D’Orcia to Siena’s Piazza del Campo, one of the most beautiful squares in the world and home to the legendary Palio di Siena horse races in July and August. Starting at either Monte San Savino or Colonna del Grillo, our biking club will lead you down a forgotten road through stunning fields of maize. Although the olive groves of Chianti are close by, the landscape couldn’t be more different. Siena will appear almost out of nowhere and we’ll enter the town through the Porta Romana, riding down cobbled streets to the city’s fan-shaped central square, the Piazza del Campo, where we’ll stop for coffee or lunch. The city is perfect for cycling sightseeing, with unspoilt medieval streets, a stunning Cathedral and the Torre del Mangia to explore. The return trip will take us through Chianti, passing through Geggiano and San Gusme, two hidden gems of the Chianti countryside, before we reach Castelnuovo Berardenga and the descent to Colonna del Grillo and Monte San Savino.
Total distance: 52 km (if we drive to Colonna del Grillo) or 92 km (without car)
Total ascent: 680 m