If you have read part one, you’ll know that my journey to Tuscany was a nightmare. My foggy lockdown brain and travelling during COVID presented more challenges than I could have imagined.

However, Tuscany is so beautiful that yesterday’s problems have melted away like pistachio gelato in the sun.


Packed neatly in a bike box, my Factor O2 VAM survived the journey to Italy (despite my constant bad luck & stupidity). However, I have misplaced the seatpin wedge/clamp, so I can’t fit the saddle. Yes, a ‘chopper’ move.

So, I am without a rideable bike… which does NOT sit well with me.

Luckily, Gabriele (my Tuscan host) has helped me secure a hire bike from his local shop, Gippo, until my replacement seatpin wedge arrives in the post (Thanks again for saving me, Rob & Factor Bikes UK).

My hire bike will be ready to collect late morning, so my usual morning #5amClub ride is off the cards. Perhaps the Universe is trying to tell me to put Becky first, not my bike?



The list of things I want to see and do is longer than Adam Blyth’s stem. I used this bike-free opportunity to show Becky the Piazza del Campo and Duomo in Siena (the start and finish of the Strade Bianche).

We set off early. It was a beautiful morning - the iconic Tuscan cypress trees cast long shadows on the empty roads, hillsides, vineyards and fields. “I should be on my bike, not driving a car.” - I thought to myself.

“Put me back on my bike”— TOM SIMPSON

Sharing this moment and view with Becky was beautiful. I think the universe was right to ban me from my bike for a few days, despite my objections.

The city was tranquillo. The locals were taking a coffee or a passeggiata (a ritual leisurely walk). The streets were being cleaned, and deliveries were being made to the restaurants and bars, anticipating the mass arrival of tourists and visitors.


We went to Nannini (Siena’s finest Pasticceria) for cappuccini and pasticcini. This was when I lost my ‘white privilege’. I know, poor me, right?

As the locals enjoyed conversation, coffee and pastries at the bar, I was swept aside and treated like I was a plague-carrying zombie (despite my face covering and hands dripping in sanitiser),  “YOU, GO OVER THERE.”

I completely understand why I was treated this way. The local newspaper headlines were broadcasting a 40%+ increase in COVID-19 cases, due to vacationers and nightlife, so in their eyes, I was a coronavirus-carrying tourist - threatening the health of the local Siena community.

“Coronavirus: Italy cases spike as infections exceed 1,000 for the first time since lockdown eased.
The rise is blamed on large gatherings caused by holidays and nightlife with many infections coming from returning travellers.”— SKY NEWS

I didn’t take this personally, at all. Italy has been hit hard by COVID - a fact we were overly aware of. In the Tuscan countryside, Becky and I were treated like honoured guests by the local people; they welcomed us with open arms (metaphorically). In the cities, we were just another transaction, with a risk.


Italy is taking things far more seriously than in the UK. It’s eye-opening. Everyone has a mask to hand, while not in use it is kept on the arm, like a band of respect for those who have suffered or lost their lives. It sends a very powerful message.

Becky and I adopted the arm-band-mask-etiquette and will continue to do so back home in the UK.


We enjoyed the romance of Sienna while it was still empty, the bells of the Duomo, gothic architecture and the elderly couples walking arm-in-arm like a window into our future.

As the streets began to fill with tourists, we slipped away back to our cottage in the countryside via Gippo to collect my hire bike.


A far as hire bikes go, this Wilier is molto bene, however, like the great Eddy Merckx, I suffer from bike-fit-OCD (If only I had his power and tenacity…). I will never feel ‘at home’ on a hire bike, the cranks will always be too long, bars too wide, etc.

Wilier make some of the best bikes in the world. Still, once you have experienced a Factor, no other bike compares in performance, handling, comfort and the unexplainable ‘ride feel’ that comes from the geometry and stiffness. Right now, I was so happy to have a bike that nothing else mattered.

Gabriele invited me on a ride to Castellina in Chianti tomorrow morning. I couldn’t wait to get on the road with some local cyclists.



Gabriele (Yes, he’s a Nibali fan, of course) and I set off from Colle Val d'Elsa to Poggibonsi, where we met Team Bike Racing Certaldo.


It’s a gradual climb from Poggibonsi to Castellina in Chianti. We rode textbook Italian style, drawing efficient round pedal strokes in unison at a high cadence. The pace was medio and would be held all day with no surges, clocking the miles as a team.


We met Wendy on the road. Her presence and energy broke the silence of the group ride. The sound of chain-chatter was replaced with people chatting. Stern emotionless faces now had smiles.


I love the cycling culture of Italy; It reminds me of the old-school club riding environment that I grew up in. There is a sense of togetherness, tradition and competitiveness.

In the wheels of TBRC, I felt like a team member for the first time since lockdown. It made me think about how much I missed my chain gang back home. Pre-lockdown, every Tuesday and Saturday we would ride cigarette-paper-close to each other’s wheels in a paceline of unconditional trust; knowing the rider on the front would snake around every pothole, carve through every corner and navigate the group safely through every obstacle and push each other.

Being ‘back in the wheels’ with this sense of comradery and togetherness, coupled with the views of Chianti was the perfect way to start my Tuscan cycling adventure.

Simon Yates?

Simon Yates?

As we cycled through Castellina in Chianti, Gabriele pointed at a restaurant, Sotto Le Volte.

“Gareth, you take your girl here. ”— GABRIELE

So far, all of Gabriele’s recommendations have been spot on. Local knowledge is far better than any travel blog or trip advisor.

On the way home, Gabriele took me on a detour to see the walled town and castle of Monteriggioni.


After this mornings ride, my mind feels clear. It’s as If I have been holding my breath for too long and can finally take a deep inhalation. The ‘lockdown fog’ is lifting.

“Are you happy now you’ve been out on your bike?”— BECKY

I took Becky to Sotto Le Volte for lunch. Now that I was relaxed, I’m sure I made (slightly) better company. Once again, Gabriele nailed it. The food was perfetto.


Becky took one sip of the Chianti Riserva, “WOW.” It had the same effect on her as the morning ride had on me.

At last, we could both escape and forget about the pandemic-travel-anxiety.

Tomorrow Gabriele is taking me in a tour of San Gimignano, and hopefully, my seatpin wedge will arrive in the post so that I can ride my Factor.

I look forward to sharing my next Tuscan Road Journal with you.



About Gareth Winter

Gareth Winter is a Senior Creative at Sky. He's had the privilege to work with Team Sky, British Cycling and WIGGINS, the names behind transforming and inspiring the UK into a cycling nation.


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