The interior of the Cattedrale di Santa Maria del Fiore. The sculptures, paintings, and frescoes of the Galleria Degli Uffizi. A stroll across Ponte Vecchio. One could spend several weeks admiring artifacts and remnants of the Middle Ages, strolling through the narrow streets of Florence. I gave myself a few days to soak in the wonders of Tuscany’s capital city before packing my bags and heading south, starting my bikepacking tour through this area of northern Italy.

I left Florence on an early Wednesday morning mid-October, the cobbled streets surprisingly void of tourists in those early hours. While fall had already embraced parts of northern Europe, it felt very much like late summer here, with mostly sunny and warm days and mild nights.

Pedaling from the old town, along the Arno river, and into the outskirts and finally the countryside, it dawned on me that I had been fooled into thinking this would physically be a moderately strenuous journey. I learned the hard way that hills make up nearly two-thirds of Tuscany’s total area, and the route on this first day seemed to cross over the steepest ones on the roughest trails possible. Up and down it went, seemingly endless. Brief spurts of riding on smooth paved country roads usually ended abruptly. My GPS often asking for a turn onto a dirt track which, inevitably, would see me laboring up yet another incline and through a forest without another human in sight. This went on for several hours. Maybe I did finally bite off more than I could chew?

Meandering through the Chianti region, famous for its production of the tart and dry wine named after it, I rolled past and, occasionally, through countless vineyards. The main winery buildings constructed with natural, exposed stone and tiled roofs, standing proudly at the end of long driveways, flanked by tall Mediterranean cypress trees, away from the main road. My surroundings conjured up images of Under The Tuscan Sun and Eat Pray Love, finding joys in a simpler lifestyle, one that is not defined by financial, but rather experiential wealth.

Eventually, I was forced to make peace with the fact that I had grossly misjudged the effort required to cover the terrain on this first day. In the early afternoon, I had to make the tough decision to modify my itinerary and use Komoot to plot a more direct route to Siena, my destination for the night. This, unfortunately, meant missing out on the dozens of preserved medieval towers forming the skyline of San Gimignano.

A dense layer of fog had a good grip on the area around Siena as I headed out the city the following morning. Until noon, the picturesque Tuscan hills remained hidden under a thick veil of mist. Not far beyond the city’s ancient ramparts, I started looking out for waymarkers of the Via Francigena. Starting in Canterbury, England, this old pilgrim route was used as a way to travel from the north to Rome and further to Apulia. Today it invites hikers and cyclists to step back in history via a network of hiking trails, farm tracks, and forest and country roads.

From the secondary roads outside Siena, I soon transitioned on to the infamous white gravel roads of the Crete Senesi, the grey coloring of the soil due to sediments deposited here between 2.5 and 4.5 million years ago. Mileposts made out of stone on the side of the road revealed these dusty backroads to be part of the Strade Bianche road cycling race.

By early afternoon the sun had burned off the moisture, and the vineyards and rolling hills were back in view. Together they provided the backdrop to the small towns and villages with completely preserved medieval architecture I passed through. In San Quirico d’Orcia, I enjoyed a quick break in the shadows of 11th and 12th-century churches. A steady, eight-mile-long climb took me to Radicofani, a commune at the southern border of Val d’Orcia. It’s Rocca (Castle) sits imposingly on top of the adjacent hill and can be seen from miles away. My visit to the fortress, sadly, was cut short. The crew of the local Rai Television Network gently reminded me to vacate the premises as they had to set up for a shoot the next day.

Traveling through Tuscany not only lets you marvel at rolling hills occupied by vineyards and romantic villas, but also some fabulously conserved towns, with histories dating back to the Middle Ages. Two of those I passed through the following day, Sorano and Pitigliano, both of them only accessible by a twisting and turning country road. The view of Sorano from the street was already breathtaking, the town seemingly built on a cliff, a tuff stone, over the Lente River. Its location and architecture, dominated by smooth facades, in light brown hues and a slight reddish tint and a lack of ornaments, it conjured up images of a fortress. Pitigliano I approached on a hiking path from the bottom of the valley, pushing the bike uphill. Medieval ruins all around, I felt transported back in time. Both towns feature the characteristic narrow alleyways as well as massive stone and masonry walls.

Slowly but surely, the steepness of the hills eased off as I approached Italy’s west coast. From my accommodation at a farm-stay in Marsiliana, I followed a dirt road along the Albegna river to Albinia. I then headed over to Monte Argentario, a peninsula connected to the mainland via a tombolo. Cycling along the narrow coastal road with the waters of the Tyrrhenian Sea on my right, I thought of the French Riviera with small bays holding crystal clear water, medieval villas, overlooking the water, peeking out from dense clusters of olive and pine trees. As I left the densely populated waterfront behind, the road quickly turned to dirt and eventually to gravel. I made my way up and around the headland, ultimately enjoying expansive vistas of the mediterranean sea to the west. Those had to be earned by navigating rough dirt roads, intermingled with some narrow mountain bike trails. The day ended in Porto Ercole, a seaside town on the eastern side of the peninsula.

Heading out from Grosseto in the morning, it did not take long until I seriously had to question the planned route I was on. Things looked reasonably effortless, most of the riding on cycleways, away from the city. But all changed after roughly 15 miles and the climb up to the fortress of Castiglione. After some more switchbacks past prime hillside properties, I found myself on rough and rocky forest roads. Grades of up to 15 percent made any riding impossible. The rugged tracks narrowed partially to trails, engulfed by the surrounding forest. I pushed the bike for most of the next two hours. I made it up and over one climb, exhausted, only to find another longer, steeper ascent waiting for me on the other side. I eventually emerged from this jungle when I was greeted by a forest worker. He waved at me friendly while operating heavy machinery to clear out an area which, by the looks of it, must have suffered from a mudslide in recent history. I navigated carefully around the excavator and found myself back on the tarmac of the main road soon after that. I ended the day in the seaside town of San Vincenzo. Strolling around town later in search of a bite for dinner, it became apparent that it was very much tourist off-season, with many eateries already shut. The lack of people meant I could enjoy the orange sunset hues from a beach, with no one else around.

The ride from San Vincenzo to Livorno was, ostensibly, a rather short and easy one. Posh-looking vineyards with signs advertising wine tastings flashed by my right as I puttered along an unexpectedly busy country road. Eventually, the route turned to the coast. I rode north on spacious, shaded forest trails, which, I could only imagine, had to be teeming with tourists and locals, flocking to the beaches in the height of summer. Right now, though, I had them almost to myself, with the crushing sound of pine needles underneath my tires. From Castiglioncello, the Via Aurelia then took me all the way into Livorno. Originally built around 241 BC to connect Rome with the northwest of the country and support the expansion of the Roman Empire, it is today posted as Strada Statale 1. It twists along the coast on mostly gentle undulating terrain, reminding me a bit of Highway 1 winding down California’s coast.

From Livorno, I continued my journey north, and, after a visit to Pisa, moved towards the northwestern corner of the Tuscany region. Not far beyond the city limits, I was back by the sea. For miles and miles, I rode past waterfront eateries, shopping areas, and beach resorts, almost all of it on cycle paths, just a stone’s throw from the expansive beach. The Apuan Alps, a mountain range stretching for 34 miles in northern Tuscany, provided an exciting backdrop and juxtaposition to the seaboard. On a switchbacking country road, I pedaled up the forested flanks of the hill dominating the Caprione promontory. I crossed over into the region of Liguria, where La Spezia, the region’s second-largest city, served as my overnight spot for a couple of days.

After a day of visiting picturesque Cinque Terre, I vaguely retraced my steps back into Tuscany, on my way to complete my loop back to Florence. I moved inland as to not cycle the same roads as before, aiming for the city of Carrara, which serves as one of a couple of anchor points that connects my family history with this region. My grandfather spent some time in this area in WWII. First, as a soldier, forced to partake in a conflict he didn’t want to be part of. Then, as a POW. He kept a diary during his time as a prisoner, as a way to document but also to keep his sanity. He was a stonemason by trade and very artistic. His diary includes various drawings, including scenes that document life in the POW camps. Earlier in my trip, I managed to visit Orbetello, in the Grossetto province, where he was stationed as a soldier. In a prison camp probably close to today’s US Army Camp Darby in Livorno, he was interred as a prisoner by the Americans. As a prisoner, he was relocated several times within Italy and eventually ended up in the then Soviet Union, from where he ultimately returned home many years after the war had ended. As a stonemason, he specialized in creating, carving, and engraving gravestones made of various types of rock. One of the most sought after materials he obtained from Carrara, namely the white Carrara marble, is still quarried there until this day.

From Carrara and through the town of Massa, a mix of heavy-trafficked main roads and undulating minor country roads took me further east. Sometimes peacefully snaking up heavily forested hillsides, these traffic arteries took me through small towns like Pietrasanta on my way to Lucca. For a couple of days, I walked the city’s well cared for historical center and renaissance-era city walls, stepped into medieval churches, and explored archaeological exhibitions below ground.

“Dove vai?” I heard one guy in the group yell out to me. I couldn’t quite make out who it was exactly, with the formation of cyclists zooming past me at significant speed. It was mid-morning on the last day of my tour, and the scenery hadn’t been too memorable on this final stretch. After suffering through some industrial areas and roads with rather high amounts of traffic, I seemed to have entered an area popular with local cyclists.

On a quiet winding country road, with empty green fields, patches of trees, and the occasional small vineyard, a group of about a dozen riders had silently caught up to me. Clad in lycra, skinny, and exposing weathered skin from way too much time spent outdoors, the group moved past me with one collective “swoosh” sound.

I could make out one guy’s question, though. “Dove vai?” (Where are you going?).

All I could do with my lack of Italian was name some of the places I had been and then pointing into the distance and uttering “Florence!”. “Grande,” was the last thing I heard from the unspecified rider in the crowd before they had all moved past me and disappeared around the next corner. Was that the seal of approval of my endeavor by an Italian road cyclist? I’ll never know. Yet that feeling of recognition of my feat stayed with me for the rest of my ride back to Florence.

My route was based on the track of the Tuscany Trail, an annual unsupported bikepacking event, starting in Massa and finishing close to Orbetello/Monte Argentario. However, since I made Florence my start and endpoint, I had to turn this into an appealing loop. I eventually settled on going up the coast from the south to Cinque Terre and then heading back to Florence.

My base for this adventure was Florence, which is served by Florence Airport, Peretola, an international yet smaller-sized airport. From there, one can either take a shuttle bus (with plenty of space for bike bags/boxes) or the tramway connection T2 to the city center.

You will ride through or past multiple smaller and one or the other bigger town on a regular basis along this route. This provides plenty of opportunities to restock on food and water regularly. One thing to keep in mind is that opening hours might differ on weekends with many places closed Sundays.

Overall, the bike handled the terrain well. My modifications to the Tuscany Trail route meant that I rode on tarmac a larger portion of the time, but still with a good amount of off-roading overall. The gravel sections around Monte Argentario and between Grossetto and San Vincenzo proved to be a bit challenging. While a mountain bike would have been more suitable, I believe a gravel bike with wider tires was still the appropriate bike for this trip.