Cycling in Tuscany

Tuscany has a timeless familiarity, with its iconic Florentine cathedral dome, gently rolling hills dipped in soft morning mist and sculptural cypress alleys – the whole of this central Italy region is postcard material. Golden wheat fields, silver olive groves and pea-green vineyards marching in sharp terraced rows on hillsides form a graceful prelude to soul-soaring medieval hilltop villages, mountain ranges and fecund forests in the north, and a garland of bijou islands beaded along the coastal south. Get out, explore, hike, bike and ding your bicycle bell, as this rousing postcard-perfect landscape demands.

Tuscany, Lonely Planet

There are so many great rides in Tuscany, so many twisting, rolling roads. The rides are much more rolling than the big climbs around Bormio or in the Dolomites, which gives Tuscany a very different flavor. If you are not into long climbs, Tuscany may be perfect for you. It’s fun to ride up into the hilltop towns that you pass; just be aware that sometimes the roads will be cobblestone or paved with tiles rather than asphalt.

I’m not giving turn by turn instructions as there are so many intersections and little villages, and it’s better to simply download GPX files from a website like Ride with GPS or Komoot. I’ve given links to GPX files for many of the rides we did, but not all of them. Some rides I didn’t think were good enough to recommend; the rides felt too industrial or there was too much traffic.

One thing to note is that at times we went the wrong way and had to double back. I’ve edited the GPX files and removed the superfluous points, so hopefully they won’t take you the wrong way 🙂

Castellina in Chianti

Castellina is a lovely, touristy, little hilltop town with a very pretty central pedestrian area.

Castellina – Radda short loop

This is a delightful loop to the north and east of Castellina, looping back through the pretty hilltop town of Radda. It’s about 26 miles with 2,260 feet of climbing. Here’s the Ride with GPS link.

Castellina – Castelnuevo Berardenga – Radda Loop

A great loop of about 56 miles with 5,000 feet of climbing. You could shorten it by starting on the loop itself but we were staying in Castellina and chose to ride to the loop. The section from Radda to Castelnuevo Berardenga didn’t impress me too much but from Castelnuevo Berardenga up through Giaole to Radda is fantastic, and includes a 4 mile climb above Giaole. Here’s the Ride with GPS link.

San Gimignano

We did a loop to San Gimignano but I don’t really recommend it as too much of the riding was on busy roads, and riding into San Gimignano was painful due to the number of cars moving almost imperceptibly. But the very wiggly SR 429 was delicious and perhaps a good loop would be to descend the SP 130 to Poggibonsi and come back up the SR 429.


Montalcino is another lovely hilltop town, rather bigger than Castellina but not quite as pretty. It has a seemingly infinite number of small streets, steps, and passageways to explore.

Montalcino – Monticello – Seggiano Loop

The ride is a lovely counter-clockwise loop through varied countryside, rolling and twisty with lovely views of various hilltop. It’s about 51 miles with 5,830 feet of climbing. It starts in Montalcino and rides through Porrona, Monticello Amiata, Arcidosso, Seggiano, Castelnuovo dell’Abate, then back to Montalcino. We rode up into several of the hilltop towns. Here’s the Ride with GPS link.

Montalcino – Monte Amiata Lollipop

This climbs 4,000 feet up the biggest hill in the area, Monte Amiata. The climb includes many sections of 10+ percent. The upper part is very wooded and you’ll be riding through a tunnel of trees. At the very top there are bars, cafes, restaurants so you’ll be able to rest and refuel. The whole ride is about 58 miles with 7,900 feet of climbing.

It’s a big lollipop whose loop goes through Castel del Piano, up Monte Amiata, down a delightfully smooth and twisty road to Abbadia San Salvatore, then up a deliciously steep hill until you eventually rejoin the stick of the lollipop. Here’s the Ride with GPS link.

Montalcino – San Quirico d’Orcia – Castiglione d’Orcia – Castelnuovo dell’Abate Loop

Yet another great loop, 32 miles and 3,850 feet of climbing, covering beautiful terrain and visiting stunning hilltop towns. This ride includes a side trip to the amazing Roc d’Orcia. We went up a new one-way road that included sections of greater than 20%. If you want to avoid this, just stay on the main road. If you go up to the Roc d’Orcia using our GPX file, ignore the short out-and-back mistake on the other side of the Roc d’Orcia 🙂  Here’s the Ride with GPS link.


Castiglioncello – Chianni Loop

I did this loop on a rather dismal day but really enjoyed it anyway. The whole loop is about 44 miles with 4,100 feet of climbing. The first 7.5 km are on busy roads and not much fun, but after that the roads are much quieter and more enjoyable. The ride starts with a long climb through Castellina Marittima, then after that there are miles and miles of wonderful rolling riding through very pretty countryside.

At one point there was a lovely feeling of remoteness and some great downhill switchbacks, but after that the whole thing feels very comfortable and pretty. I though this loop was well worth doing if you are in this seaside area. Here’s the Ride with GPS link.

A couple of days later Tanya and I did a shorter variation of this ride, finishing the climb at Castellina Marittima then contouring across the mountain almost to Santa Luce, before descending back to Castiglioncello on the same route as the longer ride. This shorter variant was about 27 miles with 2,250 feet of climbing. Here’s the Ride with GPS link.

Links and other Clicks

Other Cycling in Italy

Other Cycling Pages

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