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Tuscany Trail 2022

The Tuscany Trail organisers tout the ride as not being a race but purely as a ride to ''enjoy the beauty of Tuscany scenery, and the warmth of the Tuscan hospitality''. It is a 450 km route, of which close to 70% is off road. By off road they mean either compact gravel or walking tracks. They also encourage the riders to rest at night and not flog themselves silly as we did in Spain when we rode 'Badlands' and where riding though the hours of darkness was the norm and so too spending anywhere up to 27 hours continuously cycling (which we did) . Buoyed by the organisers description we were lulled into thinking that this would be a lot easier, by some margin, than 'Badlands" and subsequently we were both looking forward to the 'ride'. When I say 'we' I mean myself and Nick W-W who was once again partnering me on a ride. The organisers also tout this as being the worlds largest unsupported bike packing event.

The route itself takes you through the heart of Tuscany. The previous eight editions of the ride have started further north in Tuscany near the coastal town of Massa. For some reason this year they decided to map a new route that would take riders more into the 'guts' of Tuscany. It's a popular 'ride'. In previous years numbers have hovered around 1,000-1,500 participants. For some reason, and perhaps because it was the first full edition post-covid, numbers had swelled to 3,000. Given this, the organisers decided that instead of a mass start on the Sunday they would open registration on Friday at 8 am and close it at 5pm on Sunday. Once you had registered you were free to commence riding. This rolling start was probably one of the more sensible things the organisers did. 3,000 cyclists setting off at the same time has nothing but 'disaster' written all over it. Especially as some of the tracks in the early stages were narrow and technical.

Starting in the coastal town of Donoratico the route dips briefly inland to the hilltop village of Castagneto Carducci before heading back to the coastline and north up the coast to Vada. Leaving the coast at Vada the route wound itself through the national parks around Santa Luce before striking out across the plains to Lajatico and Volterra. From there it was to San Gimignano and its famous towers and then south to Siena. From Siena it headed further south to the outskirts of Montepulciano and onto the highest point of the ride at Radicofani. From here it was onto the medieval and 'Games of Throne ' type villages of Sorano and also Pitigliano before heading due west to the coast and the finish at Orbetello. A large section of the middle of the ride was along the pilgrims route called the Via Francigena. I had cycled the road route of this pilgrims way back in 2017 en-route from London to Rome. This time I was cycling the walking track. A somewhat entirely different experience.

I picked Nick W-W up from Pisa airport mid afternoon on Friday the 27th and we drove down to the start line to register. Having done the necessary paperwork it was a matter of retiring to a hotel on the coast some 5 km away and unpacking and re-building bikes before partaking in a lovely seafood dinner and regulatory post dinner gelato.

Tuscany Trail 2022. Pisa lies about 87 km to the north of the start line at Castageneto Carducci.

Day 1 - Donoratico to San Gimignano. 156 km

Saturday morning dawned (5.42 am) cool and clear and it was a 5km early morning ride to the start line for the customary starting line photo. Leaving as early as we did there were no breakfast options. We had known this was going to be the case so in an example of forward thinking the previous evening we had purchased some cereal type biscuits, a couple of bananas and some orange juice. That was breakfast. This meagre sustenance was going to come back and bite us in the collective behinds later that day.

Customary start line photo. 6.27 am . Saturday May 28th.

There were a few other starters at that early hour and the pace was relatively quick as we wound our way along various 4WD tracks and through lush fields before enduring the first climb of the ride up to the village of Castagneto Carducci. One section of the climb was so steep that even Nick W-W (who in Spain and shown a decided disdain to ever pushing his bike) had to dismount and join me in walking our bikes up the very steep corrugated concrete slope that led into the village.

As we cycled through the 'main' street of this very first town we came across a fellow rider who was evidently lost. He had little to no idea how to use his GARMIN navigational tool having borrowed it from a mate just a few days prior. Now this device is basically a sat nav for bikes. Needless to say it is probably the most important piece of kit (technical or otherwise) that you will carry on your bike. Clearly he hadn't been to the school of 5 P's. Proper Preparation Prevents Poor Performance. Nick W-W attempted to assist but with screen details in Italian even he was bamboozled. We left him 5 minutes later using his iPhone to dial his mate for instructions.

Leaving Castagneto Carducci it was a quick roll down steep gravel paths that flattened out to lead us past countless vineyards. We were now in the region known as the home of the 'Super Tuscan' wines. Five vineyards with a reputation for producing some of the best wine in all of Italy. Also home to the town of Bolgheri.

The author riding what is quite a famous stretch of road approaching Bolgheri. Known locally as the ''Avenue of trees" .

Superb snap taken by Nick W-W.

At this stage it was starting to warm up, however the roads were lined with trees, shade was abundant and our pace was quick as the gravel tracks had given way to tarmac roads. Back on the coastline and now north of where we had started we enjoyed a beachside avenue of compacted dirt beneath towering trees. With only the rare early morning walker to scare the path was relatively void of humanity and our pace didn't dip.

By mid morning we had already done 75km and stopped in Vada for a coffee and brioche. Two coffees in fact. Also two brioches. Later Nick W-W would confide in me that at this point he was going to mention that he thought this was the best start to a ride he had ever done. Good thing he didn't verbalise those thoughts. Things were to change.

Breakfast of champions. Not a breakfast you want to base a 156 km ride in searing Tuscan heat over hilly terrain on though.

Leaving Vada we struck inland and eastward and almost immediately we were thrown onto walking tracks that were both uneven and steep in places. The climb into Santa Luce was just about bearable but as we left town that climb became even steeper as the route took us along a forested 4WD track. Climbing elevation on a bike along a rock strewn track in ever increasing heat is one thing, careering down the other side is another. At this point, and whilst avoiding an oversized rock that lay mid path, my front wheel was thrown sideways and with that movement the entire bike frame jack knifed sending me in a almost slow motion style fall over the front of my handlebars and onto the rocks. Falling on my left side I think I was more amazed that I hadn't done any serious injury to myself than anything else. The bike seemed OK too. Result! Checked myself once over to ensure everything was where it should be, remounted the bike and set off on a post accident adrenaline fuelled trundle down the 4WD track to catch up with Nick. Reaching Santa Luce we paused for a sugar hit (cold coke) and a packet of peanuts.

Taking stock in Santa Luce as to where exactly we were.

Leaving Santa Luce and the forest we were soon upon Lajatico. Home to Andrea Bocelli. He of opera singing fame. Just prior to entering the village, and having conquered another very steep hill we paused to take breath and decided that we could do with a feed. We had covered close to 100 km by now and all we had enjoyed by way of sustenance since leaving the hotel was 2 coffees, 2 brioches and and a packet of peanuts each. It was midday and with next to zero cloud cover the heat was now into the high 30's. The plan hatched was to ride into Lajatico and have some lunch and then press onto Volterra. That was the plan.

As we entered the outskirts of the town the route took us almost immediately away from the centre of town and at the bottom of a steep hill, and with the town centre now behind us we realised that we had missed the opportunity for a feed. The only option was either to re-climb the hill or press onto Volterra, some 25 km away, for lunch. Onto Volterra it was.

Lajatico. Or rather, the outskirts of.

Did I mention the heat? At this point we were stopping periodically to seek shade where we could. The route was now on what they call the Strada Bianche. Basically (white) chalk-like compacted gravel. A perfect heat reflecting type surface and just what you don't want to be cycling on in 37C heat. At one point the torrent of sweat from my head was sending my navigational tool into turmoil as the beads of sweat hitting it confused it so much it turned itself off.

The views weren't too bad though.

The picture doesn't do the view justice. A carpet of red flowers at the forefront of a Tuscan Villa set against an azure sky.

We're doing a good impression of being alive and enjoying ourselves here. The reality was slightly different.

Ever wondered what a forced smile looks like? This was taken about 2 mins after leaving a rather large open air hay storage facility where we had sought refuge from the relentless heat.

Some of the houses we passed were quintessential Tuscan in every manner.

By midday Nick W-W was knocking on empty farmhouse doors hoping someone may be able to fill his empty water bottles. To no avail. The heat and hills were combining to take their toll. Dangerously so. Shortly after 1pm and as Nick W-W took a short detour to make his way to yet another farm house I discovered a small sign roadside that proclaimed '' Tuscany trail refreshments ahead - cold drinks, food , beer and snacks ''. I had to do a double take and also clear my eyes.

An enterprising local Agritourismo owner had turned his courtyard into a triage centre of sorts for desperate cyclists wanting to refuel. We pulled in and spent the next hour or so pouring as much water and coca cola down our throats as we could before casting out into the sun again and pushing on to Volterra.

Agritourismo San Giacono. We will forever be indebted to its owners industrious nature.

Volterra couldn't come quick enough. The approach however was pretty horrendous. Up a steep and very long hill that was on tarmac with quite a bit of traffic. By this stage, in terms of food, we were still running on those brioches and peanuts. At one point, mid climb, we took respite roadside in a major storm water gutter which also just happened to be in the shade. A quick 5 min stop morphed into a 30 min recovery session and then it was onto the final 2-3 km steep climb into Volterra itself. Just as we approached the gate to the historic centre the heavens opened up. Where the clouds had come from is anyones guess and almost as quickly as it arrived the rain stopped. At this point I reached for my rather expensive cycling rain jacket gifted to me by Kathryn for my birthday in March. It would seem that my fall earlier in the day had stripped me more of just pride and a few centimetres of skin. I had previously strapped the jacket to the top of my saddle bag in preparation for any rain and in order to make it quickly accessible. That jacket it would seem had taken flight when I fell. Not a cheap loss either.

Having reached Volterra at 2.50 pm we collapsed into the chairs of the first taverna we came across only to be told the kitchen was now closed for lunch. Nick W-W did a quick recce of other establishments in the square and the relief on our faces was obvious when one owner welcomed us into her fold and told us they did pasta of every manner and served cold drinks. We spent the next hour or so luxuriating in the main square of Volterra's old town downing as much pasta and bread as was humanly possible whilst watching with a degree of incredulity as the table across the way that was full of German cyclists devoured 5 rounds of beer. That be 5 pints of beer each. Mid afternoon. Impressive. We were guessing that at 4 pm they were going to be calling Volterra their sleeping point for the night.

Volterra's main street

They came in all shapes and sizes for this ride. This ostensibly being a mountain bike on steroids. Parked up in the Volterra square whilst the owners are off camera devouring a gelato each.

Volterra main square and the taverna that rescued us.

Leaving Volterra with some reluctance we still had another 30 km to get to San Gimignano which was our destination for the day. The terrain didn't really get any easier, and if anything it got a little more technical with some sections now on a very narrow walking track that had become slippery with the short but heavy downpour we had endured just prior to lunch. I was glad we had heeded our own advice of not joining the Germans and enjoyed a few beers at lunch.

If you take time to look back at the photo's I took on my 2017 ride from London to Rome you will see this exact same view taken from the exact same point. San Gimignano and its very distinct towers rising from atop a small hill in the distance. With the home stretch in front of us it was a quick ride down some lovely stretches of tarmac road, our only danger being a group of boy racers in their hotted up Fiats and Alfa's roaring by on their Saturday afternoon jaunt. The lovely thing about sign language is that it is internationally understood. One raised middle finger around a clenched fist means the same world over. I am pretty sure Luigi, in the white Fiat, who passed within a foot of me at some speed, got my point.

Towers of San Gimignano

Dating from 3 BC the old town of San Gimignano, with its Romanesque and Gothic architecture and dozen towers really is a sight to behold. Also well known for its saffron production, Golden Ham and white wine.

One of the entrances to San Gimignano

Just a couple of the dozen or so towers of San Gimignano

Our accommodation was the delightful Hotel Le Colline which was on the route as we left the town and down a small hill. Complete with pool and restaurant it seemingly ticked all the boxes. Almost. Small problem was that we hadn't booked a table in the restaurant. Seemed there was a wedding reception that night and they couldn't fit another soul. Despite the look of desperation on our faces and despite throwing all the Aussie/English charm we could muster after 156 km of cycling the receptionist stood firm. Solution one was to ride back up the hill to the town centre for dinner. Solution two was to walk 400 meters down hill to the next hotel and eat at their restaurant where there was an abundance of tables. Option two it was. A lovely dinner, followed by a 400 meter walk back up the hill with the path lit up by fireflies, was an enjoyable way to finish the first days cycling.

156 km done. Still time for more exercise. A walk to dinner.


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