Tuscany Trail was one of those red dots on our calendar since the beginning of the season. No way we would have missed that, no matter the overlapping of events that from now on will characterize the season. 

Let’s jump straight to it. Our emissaries are Fede and Frank making it an “heavy presence” with several different stories and motivations to line up at the start. For Frank is a home game and this is why he chose the Tuscany Tail as his baptism of fire on long distances. On the other hand, Fede has already some experience in the field and he feels it’s time to be back after a long absence, both from longer events and his beloved Tuscany. 

Meetup in Massa after a 10 hours car drive for Fede and a 10 pm train one for Frank to arrive smooth with the coverfue. As always Fede uploads the route at 2 am, fixes the last stuff with some ziplock and makes some sandwiches for the big day. Really, he’s one of those who love to sleep just a little during trails. Especially the night before the start. 

Saturday morning, 8:15. Ready, steady, go. A quick greeting to Fede and Nic – it’s thanks to them that we are signed up for the event. Goal of the day: make it around Siena to spend the night. After a first tarmac climb space to gravel which will be there under the wheels for a good 50 km. We have never seen a gravel section so long.

As soon as we find our rhythm Frank goes like: I can’t make it, too many memories. Every 10 km it’s a tale of a juniors race or a U23 Tuscan event of the past. “The worst cycling performance of my life: I did 7 km and dropped out; I was ashamed to go back to the team car” included.

In Lajatico we have our break for some food and the official Tuscany Trail cocktail: Coke & Red Bull. Frank is a bit worried and tries to put some calories into the tank to avoid the breaking point. But it comes nevertheless a few kms away on a quite long climb.

Coke and Red Bull. What else?

We go down from Volterra to get to this long climb and I just realize that the light is turning off! All this time I haven’t eaten that much because I was distracted by the landscape and chatting with Fede. The climb is brutal, cramps and I can barely ride: I’m done

— Frank

First long distance hard moments teach you well. You eat, be patient and wait for the light to turn on again. Fede puts some techno music on to cheer Frank up and we are in Monteriggioni by dinner. It’s dark, we have some Pici cacio e pepe, a good wine – the real Tuscany trail cocktail – and off we go to get to our final destination.

I always say I know Siena very well and I booked just a few miles away from the city. At least in my mind, because I was completely wrong and we had to pedal another two hours to get to our warm showers and beds

— Fede

Next morning an early alarm is set and we start just after preparing some ciaccini with finocchiona that Fede – the wise guy – bought the day before and had in the bags for many kms.

The down and the breakfast in Buonconvento wake us up for real and we enter Val d’Orcia with San Quirico, Pienza, fields, hills and so on. We can’t understand why there’s no category on YouPorn for Val d’Orcia. Just Unbelievable.

Some river crossing and we are headed to Radicofani, the highest point on the route. After quite a tough climb under the sun we got to the village. It’s great but it’s packed with tourists. We eventually get lucky and find our way through the small streets and get to Pane e Companatico. The owner is super nice and we have a ton of Panzanella, some cheese and a few beers. 

Time to go down. Still some climbs go up to the villages worth visiting. Sorano, Pitigliano, Capalbio. We get to meet some guys from Brescia. They’re on vacation, bikepacking – one of the guys asks if we follow a nutrition plan for such events. Did you see us good, man?

As soon as we stop laughing we are on the bikes again for the last two hours, headed to the sea to close this Tuscany Trail by the sunset. To be honest, the line is not that close and we have to push to get there with the sun slowly disappearing under the sea and Chiara waiting for us for a picture we will remember for a while (cheers to her and to her patience and talent, btw).

Just a few words with the guys

Fede: “I needed this. We did it the way I like, the right speed to enjoy the landscape, take pictures, stop when it’s worth, push when you’re pedalling. Everything was perfect, the route was smooth. I would say a “touristic gravel” ride without technical issues. I’m so happy I rode it with Frank. He was doing his first adventure. He did great and it’s only the first of many.

Frank: “Started this Tuscany Trail with a mix of fear and happiness for something I always admired but never had the courage to tackle. I suffered a bit but I understood everything goes away as long as you’re patient enough. A truly great experience with Fede – he gave me a lot of advice on how to tackle such long rides and with Chiara who appeared on some hills from time to time to take great pictures. Can you ask for more?