Biking the Montalcino Eroica Route in Tuscany

White roads, rolling hills and plenty of wine

A classic Tuscan landscape in Montalcino, Tuscany

Well-known for its fine wines, delicious food and rolling hills, Tuscany needs no introduction. While Tuscany is often associated with a certain kind of holiday maker that enjoys the finer things in life, it’s also an excellent destination for your next biking adventure. 

The Eroica is a yearly vintage bike ride originating in Tuscany, with several routes of varying lengths that pass through both Chianti and Montalcino. The routes themselves have been made permanent in a bid to conserve the environment and the importance of the white gravel roads.

The Montalcino route loops around the beautiful hilltop town of Montalcino, taking in the breathtaking views of the Val d’Orcia. You can choose from 27km for the family fun route, to the challenging 153km route and routes of varying lengths in between, with different levels of difficulty. I set out with the intention of cycling 14km to have lunch in Montalcino, yet thanks also due to my very keen boyfriend, ended up cycling the 70km route, which if you have a decent base level of fitness, is absolutely worth doing!

The Route

Bikes before starting the eroica Montalcino route in Tuscany

Starting from the beautiful agriturismo La Ripolina where we stayed; we cycled the route anti-clockwise along a mixture of white and tarmac roads towards Montalcino. I unwisely didn’t check the elevation of the route before starting and so was blissfully unaware of the most challenging part, a steep hill winding up to Castiglion del Bosco. It came as a bit of a shock and had I prepared I think I’d have been mentally ready for the seemingly never-ending twists and turns. Slowly but surely we got to the top and after a breather and some water, the hill was soon forgotten and I could admire the incredible views.

As we cycled along further towards Montalcino, we came to a fork in the road. A wider road going slightly uphill and a scrappier looking road heading steeply downhill. A car was parked nearby and as we deliberated over the map, an older couple pulled towards us offering up some advice. They had both cycled the route before more than once and advised us to take the route heading uphill to the left, rather than following the classic signpost to the Eroica route down to the right, as this one ended in another tough uphill into Montalcino, comparable to the one we’d just recently endeavoured. We took their advice and headed on the gentle uphill path which then resulted in a long winding downhill and relatively flat road, joining the main road to Montalcino. We glided into Montalcino, relieved that we’d somehow managed to escape an extra gruelling uphill, for a lunch stop. 

Montalcino is pretty busy at all times of year, and we were there in June so it was already pretty chock-a-block with tourists. We struggled to find somewhere to eat so settled on a small bar that served charcuterie boards and sandwiches. It might be wise to get there early or book ahead.

After a refreshing beer, we decided to complete the whole 70km route. The views before Montalcino were amazing, but the route kept on giving. After lunch we headed out of Montalcino, free wheeling downhill (what would have been a monstrous uphill had we taken the classic route earlier) and down into the undulating hills surrounding Montalcino. This part started on the main road but once down the hill there’s a right turn past the Cantina di Montalcino where we bumped into the couple that had given us their precious advice earlier in the day. They also recommended eating lunch at the Cantina rather than up in Montalcino since the town is a bit of a tourist trap in terms of offering and prices! Next time we’ll know.

The post-lunch part of the route was much less demanding but quite a bit longer and was rewarded with spectacular views, meandering through the rolling hills, villas perched on hilltops with their cypress tree-lined drives. Honestly just remembering it makes me want to go back and do it again. I went in early June before the days got too hot, but I think it would have a different kind of beauty in autumn with the leaves changing colours.

After a long day of dappled sunshine, rolling hills, endless vineyards and the occasional uphills, we finished up in Buonconvento, drank a much needed ice-cold coca cola, before heading back to La Ripolina for a delicious homemade feast and copious amounts of home produced Brunello di Montalcino.

Cycling the Eroica di Montalcino permanent route in Tuscany


I’d highly recommend staying at La Ripolina, it’s in such a wonderful setting and the family that runs it are so lovely. It’s incredibly peaceful and as the wifi isn’t too strong, it’s the perfect place to relax and unwind.

Another place I’d also recommend is Agriturismo Pieve Sprenna, I’ve stayed here on other trips and it’s a very comfortable option, complete with a petting farm and stables, so a good one for the whole family. 

Both have incredible hospitality, food and wine!

Views over the rolling Tuscan hills
Views from La Ripolina

Final Thoughts

I’d highly recommend cycling the route, even if you’re not a seasoned cyclist. We took our own gravel bikes but you can rent bikes or e-bikes if you’re worried that you’ll find it tough. You can always opt for a shorter route if you’re not up to the longer ones.

Happy biking!

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