Sandwiches, Sightseeing and the Strade Bianche in Tuscany

An older gentleman stands at the counter, downs his single espresso in one and throws a euro on the counter before going about his day.

It’s 11am in Rada in Chianti and the local cafe is an absolute hive of activity. Getting up to the village is a beautifully gentle climb, with vineyards dropping away to the valley floor as you twist and turn upwards. July in Tuscany is pretty good. 

When people think of Tuscany, they typically think of Renaissance art, Chianti wine, and landscapes that look like they've been lifted straight from a painting. So you’ll be forgiven for having high expectations of the region.

And on your first visit, the most sensible thing to do once you’ve collected your car, is head straight from the airport to visit the Leaning Tower of Pisa… it all feels a bit surreal.

Expectations were certainly met however. It’s not hard to find paintings, landscape photography and travel documentaries of Tuscany. It’s made for it.

Open countryside surrounds the tiny medieval hill-top towns, and bigger cities like Florence and Siena, hoover up the crowds so it can feel touristy and not at all at the same time. 

We stayed in Colle di val D’Elsa at the Relais Della Rovere. I think because it’s in a more modern part of the town, the rates for high-season were reasonable and as soon as you pull up to the hotel behind the seven foot hedge you’re hidden away anyway.

That being said, there are plenty of agriturismo hotels and villas set at the end of a poplar lined white gravel driveway, so if you want the full Tuscan escape it’s easily arranged. 

Our itinerary was, for a summer holiday, pretty packed. And yet at no point did we feel rushed or over-exerted. It’s the atmosphere of the region, it pulls you in. Why rush, when there’s so much sun and good food to savour.

Let the American tourists bustle their way around Florence ticking off all the ‘must-sees’ - you have time to pop into a local homeware shop and buy some Dolce and Gabana branded coffee. If only you’d brought the moka pot home as well…

If wine is your thing, there’s loads of it, obviously. If food is your thing, there’s loads of (they have two main courses as well as starters and deserts and it’s normal to order that and that suits me just fine).

If it’s rolling hills and gravel roads you’re after, then you’re in for a treat. It’s the setting to everyone’s favourite one day bike race that they forget is their favourite until they watch it in March and remember just how good it is. 

Touristy stuff, Florence is great of course and the Ponte Vecchio bridge over the river is a must-see. There’s a Gucci cafe in the centre and some TikTok famous sandwich shops you really ought to go to. And I’ve had clients queue to see the Statue of David and said it was worth the wait as well. Make sure you watch the sunset over the city up in the Piazzale Michelangelo but get there at least an hour before. 

Siena is smaller, quieter and the centre is a half-dome ring of paved pedestrianised streets in an arcade style around the top of the Piazza del Campo. It’s the bit they ride along at the end of Strade Bianche.

And the bit they parade down in full medieval armour and regalia during the Palio. Make sure you have dinner in the Piazza del Campo and watch the sun set while you do it, it’s incredible. 

I had two of the most memorable rides I’ve ever done within a few days of each other while we were there. Setting off a couple of hours before Jess, after a rather large breakfast and two coffees, I looped my way around the north of San Gimingnano in the baking sun before riding a lovely 5ishkm climb to the hilltop town of Volterra. Strade Bianche doesn’t venture out this far, so I’d not seen it on telly, but it’s a real cracker.

I rode straight through and descended on the other side back out into the open country. A short loop brings you back to the climb the other way, past a ridiculously nice looking Tuscan villa, and back up into the town.

Jess met me there, we had an unbelievable sandwich from a tiny backstreet deli and I sat in one of the prettiest places I’d ever visited, eating one of the best sandwiches I’d ever had, looking like an absolute state. Jess then couldn’t find the car after I set off, so I managed to beat her back to the hotel which I enjoyed a lot.

The second was a proper bucket list day. I grabbed the race route and chopped off the first two thirds of it, leaving the bulk of the ‘white road’ sectors within reach of where we stayed. Again I set off, and met Jess a bit later on at the start of the first one.

She took my camera and we staged a photo shoot. She then drove the route with me, and taking a rental car along the dusty white roads had both of us glad we opted for the full whack insurance package. 

I very clearly remember the speed at which the banged up old fiat pandas came hurtling along those white roads. If it’s hot, it’s super hot as the gravel reflects the sun, and you can’t get traction anywhere and it’s not like it appears when you watch the racing it’s much, much harder.

Feeling nearly cracked I managed to roll up to a cafe with no one in, and came back out with armfuls of espresso and ice cream. The final climb up Santa Caterina was just really,  really cool. Having been a fan of the sport for over a decade and audibly gasping when Van der Poel went supersonic up it, the fact that roads like that are just there for you to ride up always leaves me pinching myself. But a word of warning, if you want the full experience of riding into San Marcos Square and posting up like a legend, the security guards will shout at you…

Oh, and we saw the Palio while we were there and honestly it’s worth booking a trip in July or August just for that. A full medieval parade for hours before it, then 45 minutes of the announcer saying to the horse riders ‘Calma, Calma’ and these cannon shots to signal the start leaving you deaf and bewildered while it’s over in the blink of an eye. Amazing. 

There’s more. Of course there’s more. It’s a region that needs visiting again and again, and again. If you’ve always wanted to ride the Strade Bianche, or just like wine and pasta, drop me a message and we can have a chat about your next holiday.