We don’t really do holidays. Whenever my partner Claire or I go away for a week or abroad on our bikes we’re usually working or Riding A Very Long Way or a bit of a mix of both. We’re partial to the odd endurance ride and Claire had just completed a double header of the Granguanche and Dales Divide, so was ready for a bit of a rest whilst conversely I hadn’t been on a bike in any meaningful fashion for a good couple of months thanks to feeling a bit grotty, so I was hoping this holiday would be the gentle opportunity to ease my legs into going round and round again. None of this really happened.

On top of this, the trip had been postponed for over two years because of the Bad Thing, so we were both eagerly desperate to take a break from the world via this bikepacking-ride-around-Tuscany-trip, taking in as much of the famous strade bianche white roads, pretty villages, coffees and ice cream as we could. Fly to Pisa, train to Lucca, ride to San Gimignano, Pienza, Montalcino, Arezzo, Gaiole in Chianti, Volterra and back to Lucca in a long week wobbly figure of eight of just over 650km. 

When your travels often include dawn to dusk riding and then a bit more before grabbing some sleep under a hedge after a supper of petrol station snacks, deliberately planning no more than 100km a day including a scheduled day off in the middle (with a short unloaded bike ride option), your handlebar pack full of normal clothes instead of bivvy kit and staying in accommodation with beds and indulging in proper sit down food each evening, it’s more than a holiday, it’s five star luxury. That’s what I told Claire anyway.

The route was stitched together from a mix of reference material including bits of the Tuscany Trail, some of the Via Francigena long distance path, sections of the L’Eroica bike route, some stealing of friends GPX files, and a smattering of local knowledge from the many times I’d previously been in the area. There was also a lot of looking at walker’s maps on the bits I didn’t know, using heatmaps, endless zooming in on streetview and plain old guessing and hoping for the best late into the night in the preceding weeks. 

We’d come here ostensibly to ride a bunch of strade bianche, the iconic white roads of Tuscany, and while we did a whole load of that, we also covered just about every other off-road surface you could mention. Rocky descents, sandstone slickrock, ancient cobbled roads, field edges, concrete paths, wooded singletrack, a couple of river crossings, sticky sand, sucky damp silty earth, drifty corner marbley fire road that’s actual made of marble, deeply rain rutted tracks, trails that would have been better suited to a mountain bike and a few trails where we had to fudge a detour around something that looked just a bit too much for our 700c tyres.

Even the tarmac had a wide variety of character, from pristine 5kph faster hero blacktop to amusingly deformed asphalt waves and one landslip that took out half the road where no attempt at a repair had been made, they just repainted the white lines around it. And then that lovely tarmac can suddenly give way to gravel, and without warning, switch back again. The definition of road here is pretty fluid, which makes it perfect for the bit of everythingness of a gravel bike. 

My first trip out here was on a proper road bike with rim brakes and 25mm tyres, the fattest I could fit at the time, and while it was a whole lot of fun piloting an entirely inappropriate bike down the strade bianche trying to emulate the pros of the spring classic race, it required quite a level of finesse, elicited some puckering and may have hastened the formation of a crack in the frame. Whilst some riders like the challenge of riding strada bianche on even older, tattier, mechanically challenged bikes for the L’Eroica vintage bike event, doing it on something with fat tubeless tyres, disc brakes and stable geometry may not be as heroic but it’s definitely more confidence inspiring and enjoyable, especially when it’s loaded down with a week’s clothing.

Day one had to be hastily rearranged as an ugly swathe of thunderstorms were forecast to sweep across the area and the idea of covering ourselves and our bikes in Tuscany’s finest grit and grinding everything to a soggy pulp at the very start wasn’t too appealing, so a tarmac-only option to our first destination of San Gimignano was plotted. The rest of the week had twenty-degree sunshine bursting out of all the weather apps, so it was an easy sacrifice to make. The skies were grey, but a light grey, on our departure from Lucca and we stopped for coffee and buns less than 100 metres from the hotel. Holiday mode engaged. 

The idea was to have a swift breakfast and get as many miles in before the weather hit. We managed a couple of hours of riding before we could ignore the fat spats of rain no longer and shrugged on waterproofs. Splooshing across a scruffy town and through gutter rivers wasn’t pleasant, but thanks to a fortuitously placed village cafe we found brief dry solace with a hot drink and buns, only for a short while later to be forced to shelter under trees as a painful rain and hail mix bounced off the road. The decision to stick to tarmac seemed incredibly wise. 

We eventually rode through the northern gate of San Gimignano and climbed its dark shiny wet streets to our stop for the night and fumbled a phone app controlled front door with chilly fingers. Recovery sandwiches and using the chain breaker from a multi-tool to open a bottle of wine later, a rainbow signified that it was nice enough for a meander under the town’s famous ego trip towers before we lived it up with take-out pizza in a 16th century vestibule. 

We left San Gimignano next morning just as the earliest coachload of tourists was unloading and in under a minute we were whooping downhill on the first white dusty off road of the trip. A lot of the first half of the day as we headed towards an agriturismo near Pienza would be on the Via Francigena, the pilgrimage route that runs from Canterbury to Rome and then on to Apulia in Italy’s heel if you wanted to keep going and hop on a ferry to the Holy Land. It’s incredibly well signed with the familiar red and white markings of many of Europe’s long-distance routes and it’s quite mountainbikey in some places, which made it a fun-bumpy tongue-out shimmy on fully-loaded gravel bikes. 

Unbeknown to us today was Liberation Day, Italy’s version of our VE Day and a national holiday, so everywhere was busy, the trails swarmed with people taking their day off in the hills and our route through Siena for a quick freewheel past the famous bits and our lunch stop was frustratingly slow and stressful as the honeypot town was even more crowded than usual. The sudden reveal of the Piazza del Campo was still impressive though, and we even had a nose down the street that the Strade Bianche road race comes up during its knee busting finale and can confirm that it is indeed bloody steep.

While it’s nice to visit the Tuscan tourist favourites like Siena, Florence and Pisa and gawp at the sites, it’s not strictly necessary - Pisa is just the tower, as one of our hosts said, although it’s worthwhile for the tragicomic scenario of no-one paying any attention to the famous landmark but everyone taking a photo of themselves trying to hold the leaning tower up. It’s a horrible cliche and no small amount of travel snobbery but you only have to take a few pedal strokes to avoid all of this, and there’s a lot of Tuscany to do it in - crest any hill and it stretches out in front of you to all far horizons. It’s a large place and it’s also very very empty. Even the bigger roads that looked to our UK eyes like they might be busy weren’t. Head off road and you’re really very much on your own. 

Despite there being evidence of centuries of human habitation and agriculture all around you, it’s fantastically, heart soothingly quiet. Stop and you’ll hear nothing but the rustle of a lizard in the dry brush, or the croak of frogs in a pond. Wait a while and you might see deer prance across a field or the lazy loping of a hare. Be unlucky and you’ll have to sprint past a gang of large vocally protective sheepdogs. Some of the trails we pointed our wheels down were obviously more underused than the maps might suggest, so we had to reroute a few times, push once or twice, endure one very long and grumpy “This was definitely a path last time I was here” walk through a tall field of crops only to find that a farmer has secured multiple gates to keep people and animals out of his vines. We probably also lifted bikes over fences more often than was acceptable. Best to try and ignore all the discarded shotgun shells on the ground and pedal on swiftly and silently and rely on the fact that you haven’t seen anyone for the last couple of hours. 

Thanks to modern online booking systems, sorting out accommodation from afar was a lot easier than it ever has been. The hardest bit was finding somewhere in Lucca that could look after our bike bags for the week while we were noodling about. A big shout out here to Hotel Bernardino for being incredibly kind, welcoming and having a spacious boiler room. Being cautious and paranoid, I tried to find places with keyless entry so there would be less chance of any “You can’t bring those in here” bike discussions in a language my frantic Duolingo learning hadn’t quite levelled up to, but I needn’t have worried, Italy is a bicycle loving country and there was always welcome space for our bikes, beyond being asked where we’d come from, they hardly even registered. However, I knew for certain that our second night’s stop at Podere Spedalone near Pienza was going to be a welcome one, as I’d visited here often when I worked as a bike guide in the Before Times. It’s wonderfully only accessible via white road and I know the owner well enough for welcome hugs like an old friend. It also has the best view in Tuscany from its terrace, but don’t tell anyone. 

Italy was until relatively recently comprised of multiple independent states with the propensity for a little squabble with the folks next door, so a lot of towns are built on the tops of hills - great for defensive purposes but not so great for cyclists at the end of the ride. Our next day saw us climb up to the same town twice, once up to Montalcino on the steady tarmac main road and a brief stop for sandwiches and ice creams, and then again a long loop later into the back of the town via an off-road route that looked kinda fun on the map. In reality it was a never ending 20% climb that just got steeper every time the concrete road kinked round the corner, it was one of the most brutal climbs I’ve ever done but the views were lovely and we could see where we started the easy road climb several hours earlier that day. It did require an emergency trip to the supermarket for snacks before moving on to supper though. 

Tuscany can be alarmingly lumpy, in all of the places I’ve ridden a bike, it’s where I’ve bonked the most frequently. I think it’s a combination of none of the hills being particularly big, but as they’re all different sizes and shapes, there’s no rhythm and they’re just too much fun, so you’re tempted to exuberantly attack each and every one of them. It’s always been a happy bonk. On top of all the usual hilliness, I somehow managed to find at least one absolutely vicious profanity-strewn climb every day of the week. There was the steepest bit of tarmac into Siena and deciding to include a nice little diversion to Cortona on our way to Arezzo because it looked pretty, led to a real grunt of a climb in the heat of the day which made sitting in the shade of the middle of town with nibbles and cold drinks all the sweeter. And then there was the nice-and-wiggly-on-the-map-but-actually-quite-sweaty climb over the ridge of hills that protect Arezzo. Paying attention to elevation profiles isn’t my strong point, apparently.

Our visit serendipitously coincided with the Italy Divide, a 1250km bikepacking event that travels from Pompei north to Lake Garda, and a quirk of our travels is that we’re going in the opposite direction, so while there are waves from both sides, there are looks of bemusement from the more tired and grubby riders wondering why there are other bag laden cyclists going the wrong way and smiling. We bump into a couple outside a supermarket and while the itch to be joining them is strong, it’s nice to know we’ll be spending the night in a comfy bed and not pedalling through to the dawn or looking for a comfy barn and grabbing a fitful nap. 

Whilst we’re hopping from place to place, there’s a scheduled stay in Gaiole in Chianti for a couple of nights for the chance of a bit of a relax, a day off if necessary, the chance to properly clean some clothes (there was an unexpected bonus of a washing machine in the accommodation, hurrah!) and the option of a 50km loop with the skippy lightweight joy of not having any bags attached. Of course, we went on the ride and even though it was a short day, it still involved getting a bit lost and a fair bit of spicy climbing. The coffee, bun and ice cream count was sufficiently high to count as a day off though. 

Which brings us to the important stuff - food. Tuscany has traditionally been a poor region, ignore all that fancy wine, and its cuisine reflects that, it’s simple and hearty and exactly what you’d need after a day in the fields or in the saddle. It’s famous for its salt free bread and pappa al pomodoro - a tomato and bread soup that makes a filling starter. Wild boar also features heavily. Local shaped pici pasta (like a fat spaghetti) with a cinghiale ragu was mopped up, fare la scarpetta, with a corner of that bread with hungry-legged gusto. On the road we were never short of ride food. Italy does a fine snack stop, and they’re very good at bar-tabacchi which do coffee, beer, some kind of pork and cheese filled breadstuffs, pastries, fizzy drinks, crisps, general supplies, toilet roll, cigarettes and Lotto cards. 

A large part of the culture seems to involve sitting outside watching the world go by discussing something or other with arm waving, so to avoid getting sucked into any tourist traps it’s best to head for somewhere that has a couple of old men sat outside and join in the sitting and watching. It would be remiss not to mention the coffee, it is universally of good quality, and thanks to government-controlled prices is cheap too, so you can save weight and leave your bikepacking brewing paraphernalia at home. Just be aware of the no-cappuccino-after-11am rule to avoid an international incident. The Fanta tastes better here as well.

It’s easy to get picturesque fatigue and culture weariness here because there’s just so much of it, and we began with a high bar. Our start and finish point of Lucca is a walled town, and not just your common town wall, but one that’s 30 metres deep with a tree lined traffic-free road circumnavigating the top. The streets inside are old, narrow and maze like. There’s a tower with oak trees growing out the top. There’s a pretty Romanesque church, and another one. There’s a gold fresco adorning the front wall of that one, and we stumbled upon the mummified body of the Patron Saint Of Lost Keys so the rest of the week had a lot to live up to. 

Luckily Tuscany isn’t backwards in being forwards with pretty - sensuously curved hills, postcard villages, trademark cypress tree lined roads, old Fiats, farmhouses perched on horizons, cypress tree lined ridge lines and a beguiling light that makes you want to become an artist. Slices of pizza sat against a wall in front of a stunning Romanesque-Gothic cathedral, meh. 

There is always a counterpoint though and such is the way with long distance travel that we had to schlep through some crappy bits and Italy does specialise in dumping scruffy industrial estates and lifeless factory units in the middle of somewhere pretty. Finding a way in and out of some of the larger towns - especially the last day on the flatter land towards Pisa and Lucca, meant making our way through inescapable ordinariness of daily life and too many intimidating roundabouts. The country isn’t all the passion, romance and style it’s stereotyped to be because it needs to make a living somewhere. And while we romanticise and idolise the strade bianche - enter the Eroica shop in Gaiole in Chianti and you’ll see just how much, they’re still ordinary working roads and not just something for us to play out our hobby on, so instead of streams of gravel hunting cyclists you’ll meet someone using them to merely go about their daily business, a car, works van or garbage truck could easily be coming the other way.

Whilst I knew a lot of where we were going over the week, there were large gaps in my mental map at the beginning and end, the itinerary was based on where might be nice, what looked interesting and what was a suitable distance away. It was great to revisit some roads and gravel sections that were among my favourites in the world, but it was even better to discover that some of my route guesswork would reveal a road that would immediately find itself in my best ever list. Our penultimate day from Gaiole in Chianti to Voltera had been a frustrating one. Another painfully hot steep climb or few, stuttered by a track constantly barriered by gates. An overly long section of making-up-the-distance tarmac that was too motorbike friendly and a vague path with a Crystal Maze crossing over a stream made forward motion feel bitty and anxious on a hot day. 

But stopping at a junction as a rutted sunken farm track emerged onto dreamy hardpacked gravel, we could see Voltera above us and were able to finally text our Airbnb hostess that we’d be arriving soon. The small insignificant singletrack road that curved and switchbacked the last few kilometres to the town, planted on top of the hill surrounded by its thin lozenge of walls, an imposing barrier to any wannabe invader, turned out to be one of the most fulfilling roads I’d ever ridden. The late afternoon glory light might have helped. As may the expansive view down towards southern Tuscany. As may have done the “It’s Just Us” quiet, but it was far, far better than any famous tick-list climb you might care to mention. 

Maybe it was also because we’d made it all the way here over a long week with all our stuff - that’s always a rewarding feeling. Voltera itself didn’t disappoint either, not overly touristy and small enough not to be frantic. I might have to spend a fortnight there sometime to see if I would ever get bored of the multiple ascent options back into town before I decide if it’s my new favourite place. The obviously locals’ choice restaurant at the top of the steps just inside the walls where they had to get the English speaker to take our order is a big mark in its favour too, but maybe that’s just a week’s feisty riding talking, as I’ve never seen Claire eat so much so quickly.

It turns out we can’t really do holidays. Our supposedly gentle bike tour ended up being quite hard. Each day somehow included at least one horrific grind up a steep hill and a muttered sweary push along a path that wasn’t there, and the planned less-than-100km-a-day-taking-it-easy seemed quite enough thank you. We didn’t take the day off and rode what most people would consider a decent day out instead, and neither of us can remember when we did eight days in the saddle in a row. But we didn’t have a little exhausted cry, we didn’t sleep in a ditch, we didn’t wonder why we were doing this, we stopped lots for coffee, and ice creams, pistachio cannoli and to look at the view because it was always well worth stopping for. That counts as a holiday.

Bike stuff

 Claire was on her Mason Bokeh with Hunt wheels and WTB Nano 700x40c tyres, full Shimano GRX groupset with a Wolf Tooth front ring, hauling stuff in Restrap bags. Jo was riding his trusty Kinesis Tripster AT with Bontrager GR2 tyres, a Shimano GRX/XTR Di2 mashup and strapping extra snacks to Apidura bags. Didn’t have a single mechanical issue.