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Cycling Tuscany: Raiding Radda-in-Chianti


Little did I know that Tuscany was going to be a scorcher in July, 2015….and neither did my lovely guests, the Rowlands group consisting of Zizz and Nick, Martin, Lennart, and their non-riding partners Amanda and Caroline.

Luckily for Nick’s group, they got in touch with the right person to design and plan their cycling adventures around Chianti and Tuscany. The initial consultation was simple enough to understand what sort of challenges would work well for the group as a whole so no-one was stretched too much or would be left wanting more, bearing in mind the temperature would be a considerable factor even with early starts. Staying at Relais Vignale, Radda-in-Chianti made a perfect base to venture out and explore the stunning area in the precious time available.

As part of my proposal I recommended a combination of what are probably the most iconic rides around Chianti and this part of Tuscany. Florence and Siena are situated north, and south-west respectively, within striking distance from Radda. Our itinerary made sense to take advantage of the quiet back roads and make our cycling pilgrimage to both of these renaissance cities in the heart of Italy. Nick agreed.

As an added bonus, we were also located in prime L’Eroica country, and a stones throw from some of the Strade Bianche gravel roads used for that iconic event and also the Eroica Pro professional southern classic. This served to work really well in breaking up the longer days, with the novelty and fun of riding some high profile gravel roads. Here is the account of the full trip….


Having only spoken to Nick on the phone I was anticipating meeting the group the night before, as part of an informal briefing for everyone, it was great to see everyone so relaxed and enjoying their trip so far with the main highlights still to come. The group had already ridden a self-guided loop which I had designed before they had arrived at the Relais. This acted as a nice introduction to the area and a warm-up for the coming days.

Although concerns were expressed over the difficulty of effort, I highlighted that our agenda wasn’t rushed and the great coffee and ice-cream stops en-route would provide the necessary fuelling and motivation! After our little chat, everyone was more relieved entering dinner knowing that I wasn’t a merciless tour guide hell-bent on military timing and maximal efforts to keep up…… ‘l’Italia non può essere affrettata’, Italy can’t be rushed.


Day 1 Radda to Florence (100km, 2000m)

The first morning I eagerly made it up the road into Radda and the Relais, along with emergency provisions on my back as this would be a supported ride without vehicle. That initial ascent kick started my pulse and was buzzing for the groups cycling antics over the coming days with me. I was pleased to see everyone enjoying the last items of their breakfast on the vine covered balcony with a fantastic view over Chianti. Naturally, like all good Italian hospitality I was offered multiple coffees, so I opted for the standard macchiato, as I already had two cappucios down the road at my own lodging. I could sense the group were slightly nervous, which is normal on the first day so I opted for a few departing snaps to capture the moment along with Lennart and Martins wives, Caroline and Amanda who went off for a ramble in the lush countryside.


After bidding our farewells and promising to return everyone alive and well we set sail in descent through the village and the vinyards towards Florence. Our first hurdle of the day came almost immediately as Lennarts tube valve decided to take a trip also and popped out while unscrewing his pump (seems to be quite common). Instead of wasting time changing the tube I tightened it up with a pair of pliers as they tend to reseal themselves under air pressure.


Italy doesn’t have very forgiving terrain for cyclists, and is the reason why the Giro is often the most exciting of all UCI Pro-Tours…the biggest effort of the day came earlier on the ride,  with fresher legs before the heat of the day really kicked in. The climb up to Albola was conquered by everyone very well, and were rewarded by smiles and views looking back over Radda. Onwards we headed towards Florence, with the rest of the route being relatively flat or in descent down Cipressi tree lined roads and vast panoramics of the green vallies below. The roads around here have been frequented by professional cyclists racing the Giro and none more famous than that of Gino Bartali (famous for his Giro success and covertly messenging important documents in his during the second world war, undetected by the Nazis). Gino lived in Ponte a Ema, just outside of Florence where a museum now stands to commemorate his life. We stopped just outside of Florence for a few more coffees and to refill the boracce.

Approaching Florence, the historic capital of Tuscany which was home to the likes of Michelangelo, Dante and Giotto felt very spiritual for the group having made the pilgrimage effort under their own steam. We entered the periphery of the city on much quieter roads than readily available, where our half-way point was the piazza Michelangelo with iconic views over the river Arno, Duomo, Ponte Vecchio making up some of this architecturally delightful vista.


With visual overload we turned back for our lunch stop in Impruneta, a simple pizzeria, with very welcome air conditioning. By this point the group had started to spread out on the long ascent out of Florence, and Lennart felt that he was let off his leash somewhat, it took a concerted effort of trying to catch up with him, and signal vocally so he would not miss the next main turning and add unnecessary distance and climbing to his day. Keeping a small yet varied group together sometimes takes much coordination and a little experience!  The noon sun was hotting up as expected, so we topped up our bottles from fresh spring water from the fountain in the piazza and I led our band of merry adventurers back towards Radda, although with some effort still remaining, we were helped along by a welcome tailwind.


We headed up through some great little vinyards, Luiano, on the ridge road avoiding the busy SR222 and all the heavy traffic it carries. From here the road starts to get quite rolling with one or two longer and steeper sections through Quattro Stradale, so I thought I would be well positioned on one of these viewpoints for a great photo of their for their cycling holiday albums. Martin however had other plans and steamed well ahead, carving up the rollers and long rises not to be seen again. A while later we came across his pair of glasses crushed in the middle of the road, more than an ominous sign and I was somewhat concerned after promising to bring him back in one piece…quickly trying to think of excuses why Martin hadn’t made it back with us! After searching for further signs of a crash or wreckage to no avail, Lennart and I were still puzzled and broke the news to the others. A couple of miles further on I caught a flash of blue in the distance and made a harder push to make sure I wasn’t hallucinating. Massively relieved, Martin pulled over and we all re-grouped. After witnessing some composed expressions for the camera in the climb, we made a final stop in Panzano to catch our breath and soothe our overheated torsos with some of Chiantis finest gelato, in the shade.


We arrived at the Relais, happy as promised with the elation of achieving Radda to Florence and back, mission accomplished!


Day 2 Gravel roads to Gaiole and wineries 35km, 600m.

This day was purposefully shorter, to recover a little from the bigger ride yesterday and also not take too much toll before we venture south to Siena on the last day.


The focus was to get a feel for the notorious strade bianche which started almost immediately after leaving Radda. First though, we soaked in the morning air at the breakfast balcony shaded by thick vines, we finished our coffee and rolled out to beat yet another warm day….only to realise Nick hadn’t joined us in the descent. After a few minutes Nick came tentatively across the roundabout with one leg held out before pulling up next to us and explaining that his cleat had snapped off. As part of the Bicissimo touch, I delved quickly into my magic bag and pulled out a fresh SPD and the group was soon on its way for some great gravel riding without much delay!


We were soon on the last stretch of the infamous L’Eroica route, so it was perfect to grab a snap of those beaming smiles before the fun began.


The section to Vertine is lovely hard packed gravel and not too technical in elevation, so it worked really well as an introduction before more of the gravelly stuff on the final day to Siena. We couldn’t help but sneak a peak in the Castello di Vertine also.


Within a few minutes we were down into Gaiole town, the official start and finish of L’Eroica, so we paid homage to all those bygone days by downing a few celebratory cafés…as a cyclist one espresso never seems enough.

Opposite is the L’Eroica boutique also known as White Roads run by Emanuele….selling some very nice official Eroica attire and accessories. As to avoid the temptation I stood watch on the bikes while the others browsed for an imminent return by car (just twenty minutes drive from Radda). Emanuele kindly offers all Bicissimo guests a generous 10% discount.


Onwards and upwards we went, although we were sure to fill our bidons to the brim, as temperatures were still to peak at 34C and the sun was strong. I led the group up a great little climb past the infamous wine producers at Meleto, more of a shallow, comfortable ascent, which topped out near the wine cellars at Castagnoli.


This was our turnaround point for the short morning ride and we took the blowy decent back into the lower valley road were it was a free-for-all to get back to Radda…..and the desperate urge to sample some of the great Chianti on the veranda with spouses at the Relais in a well-deserved fashion. Lennart possibly won that one with Nick not far behind. I suggested a solid recovery afternoon would help for tomorrows adventure to Siena and lunch in the Piazza del Campo.


Day 3, Radda to Siena, 73km, 1,500m.

Martin reluctantly passed on todays adventureto after realising he dug too deep during his ‘time-trial’ effort on the way back from Florence yesterday. Nick had decided to take a breather today too as he was feeling a little sore, and instead came along in the car as moral support, with his bike ready to venture into the heart of the city with us. The route on the final day was also rather special in that we followed some more L’Eroica roads, and with spectacular views of Siena steadily approaching us.

I had the pleasure of Zizz and Lennart’s company with Nick a little further behind on race radio, enjoying the views on four wheels and acting as fill-in photographer for the day to relieve me of some of my duties. Our first break and a chance to make some bike adjustments was at Castello Brolio and Barone Ricasoli, a very famous producer of Chianti wine…but avoided the stiff little climb to visit the actual castello above us, to save some energy for the steep Cypress tree-lined ‘muro’ at Pieve a Bozzone, before lunch.


Naturally not all Eroica roads are gravel, and our ridge road south following the route provide a great respite for us to enjoy the southern Chianti countryside and chat at length. I could hear Nick was becoming frustrated that he wasn’t riding that particular section, although this soon passed when we hit the muro! Everyone pretty much scaled the 18% average for 300m without fuss, and was a good inclusion to wake up the legs on what is essentially quite a fast arrival to Siena from Radda, with well under half effort before lunch.


We navigated the quieter roads into the periphery of the walled-city from the east, which led us to Porta Pisini, where we waited for Nick to park up and mount his bike to join us on the medieval part of Siena’s wonderful architecture. Siena is built into the top of a hill, so has obstructive entrance for bikes as the cobble roads can be quite steep. This is exemplified by the finish of the Strade-Bianche Pro Race finish, where Via. Santa Caterina (16%) often decides who the winner is right up to the final few metres. This time we settled for the gentler entry point to the Piazza del Campo, twisting through the vehicle restricted narrow lanes of Sienas historic centre. Navigating ‘oblivious’ tourists becomes a skill, and is one of the reasons why Sienas council is considering banning cycles in this main tourist attraction of il Campo, and I imagine the authorities will be very strict in imposing fines on all cyclists, knowing how Italians are sticklers for rules.


After a quick lap on the sacred cobbles where the Palio takes place, we made a bee line for the Fonte Gaia to quickly refresh and lock up our bikes before delving undercover at one of the better eateries, Al Mangia, est. 1937, provided front row seats of the fab view of the piazza and domineering bell-tower. Although quite touristy, they provide an exceptional choice of pasta dishes. I called ahead to cancel our contingency plan of stopping at Malborghetto on the way back from Siena, with a rustic ambience in the small village of Lecchi. Usually, if you aren’t seated for lunch before 2pm then you haven’t got a hope in hell getting something to eat until dinner time. The cooks don’t hang around for dawdling cyclists, and there was still a fair bit of elevation to reach that stop. Instead we took our time at Al Mangia and racked up coffee after coffee, and started thinking about riding our bikes before the guilt of our prolonged lunch stop kicked in and not soon enough before I bored the others with my limited knowledge of the feuding Guelphs and Ghibellines of Siena. We soon said arriverderci  and were on our merry way without getting lost in Sienas back streets. Nick was back in the car and we were spinning the legs ready for the first rises out of the city, as we traced a couple of the roads we came in on before turning off onto some very picturesque narrow, walled lanes devoid of traffic. We rode steadily, with no rush to be back except for dinner. Italians can be quite ironic or abstract even, as the route we passed rather bizarrely has a couple of old British red telephone boxes on one junction, and giant caricatures randomly hiding in tall fir trees.


Nick had driven ahead to check the section of gravel road we were heading towards as sometimes, without too much traffic or after poor weather conditions can be left in need of repairs, but was thankfully acceptable for our riding. We were now in more isolated areas, exposed to the sun, so we took a necessary break to hydrate and some more photos. Although I can sense my two-wheeled companions were growing more weary I comforted both in the knowledge that we were just 2 climbs away from Radda and the relais. Lennart started to get a little frisky on the descent after the first, and we had gapped Zizz quite considerably by now…although with Nick in her vicinity. Lennart kept the effort going on the last climb before I called it a day as he disappeared off up the climb to victory (carrying a heavy pack was my excuse). I double backed to ride the final stretch with Zizz, with lovely views of Radda in and out of sight as the road snaked up towards the vinyards south-west of the village.



Once back at the Relais, and three great days riding behind us, I was invited for aperativo and celebrations of the groups successful adventuring around Tuscany and in appreciation of achieving more than they imagined before coming to Italy for their Bicissimo experience!

  simonc   Nov 02, 2017   Chianti, Custom, L'Eroica, Self Guided, Strada Bianchi, Supported, Tuscany   0 Comment   Read More

EST! EST! EST! Vin-aggiatori a Roma

  In July 2017, newly weds Harry and Maria Bunnell embarked on a two wheeled crusade from Firenze (Florence), Toscana to Roma, Lazio in the ancient slipstream of Johannes Defuc (a Bavarian bishop) who was ordered to Rome in 1111 under the instructions of emperor Henry V. Defuc, as a connaisseur of wine, sent his servant, Martin, ahead […]

  simonc   Aug 27, 2017   Blog, Chianti, Custom, L'Eroica, Lazio, Self Guided, Strada Bianchi, Tuscany, Umbria, Vino   0 Comment   Read More

WhiteRoads – L’Eroica

A Radda Reccy Even after just a short history, the Strade Bianchi- Eroica Pro race  (ex Monte Paschi Eroica) is now considered one of the early season classics or monuments raced by many of the same names as Amstel Gold, LBL and of course Paris-Roubaix. Le sterrate or ‘strade bianchi’ are Italys version of the cobbled classics. A […]

  simonc   Jul 22, 2016   Chianti, L'Eroica, Strada Bianchi   0 Comment   Read More

Italian Custom – Titanio per sempre!

Italian Custom – The search After what seemed a life-time of riding my trusty Wilier Triestina Izoard, a well-engineered monocoque machine bought at Filipos (ex-MTB Italian national champion) Dieffe Bici Wilier Punto Rosso store. Known previously as Bicicli Verona, is probably one of the best road-bike stores in Veneto. Bicicli was my local bike shop […]

  simonc   Jul 10, 2016   Custom, Titanium, Tuscany   0 Comment   Read More

A Garda Grind- Punta Veleno

More big names passed under my wheel and then I caught a glimpse of the sign post on the side of the road. PUNTA VELENO, Arrivo 5km, 16.9%. Ok so now it all made sense, I had heard about the Punta Veleno. I knew it was in the Garda area somewhere. Basically I randomly found one of the toughest climbs in the whole of Italy on a scorching hot day. But, I didn’t want to give in so early like my fellow German holidaymaker, with this new information I wasn’t going to let this climb beat me, although it was doing a great job already.

  simonc   Nov 27, 2014   Blog, Climbing, Self Guided, Veneto   0 Comment   Read More

On a Tuscan High – Monte Amiata

While on a reconnaissance trip to Alta Maremma during the World Championships in Tuscany, after a weeks quiet riding in the spectacular Metallifieri hills we decided to venture further afield on the last day. We were in striking distance of Monte Amiata, the highest point in Tuscany at 1,750m and only one of two places for Florentines to ski in Tuscany (the other being Abetone on the Emiglia-Romana border). Even though we did’t have much left in the tank after a solid weeks riding in the warm September sun, it felt rude to miss out. Seggiano at the foot of Monte Amiata (an extinct volcano), is a one and a bit hours drive south-east of Massa Marittima. The road from Seggiano is the classic way up, a 19km climb and 1,284m elevation at 6.7% average.

  simonc   Nov 12, 2014   Blog, Self Guided, Tuscany   0 Comment   Read More
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