Grand Tour Italia - Rome to Florence

This last week was one of the most amazing experiences I have ever had on a bicycle. Two years ago, I joined Volta Pro Tours to cycle from the top to the bottom of Portugal. It was, without a doubt, the toughest ride I've ever done in my life. I joined Volta once again for the inaugural edition of what they're calling the Grand Tour Italia; a beautiful and challenging 450km route that winds from just outside of Rome to the southern edge of Florence. Much to my chagrin, I didn't take enough photos during my trip through Portugal, so I committed to being a little Ansel Adams during this journey - it's not one I ever want to forget. Let's go!

Day 1: Orvieto to Assisi

Your journey begins atop the tufa cliffs of Orvieto, a city that seems to rise organically from the rock itself. Once a major Etruscan stronghold, Orvieto later became a papal refuge, and its magnificent Gothic cathedral — with its mosaic façade glittering in the morning sun — is a fitting send-off. As you descend from the plateau, the road unravels through the Umbrian countryside, a patchwork of vineyards, silvery olive groves, and oak woodlands. The landscape is serene but alive — you might glimpse a hoopoe bird with its striking crown or a herd of sheep guarded by a shaggy Maremma sheepdog.

Midway, the road skirts quiet villages like Deruta, famous for its hand-painted ceramics, and Bastia Umbra, where Roman roots meet rural charm. Eventually, the slopes of Mount Subasio come into view — a soft, forested massif that has stood sentinel over Assisi for centuries. Assisi itself is a place of pilgrimage and peace, known around the world as the birthplace of Saint Francis, the gentle friar who preached to animals and renounced material wealth. The Franciscan ethos lingers in the air, blending with the scent of lavender and rosemary that grows wild in the hills. You arrive not just at a destination, but at a sacred pause in time.

Day 2: Assisi to Città della Pieve

Leaving Assisi behind, you roll westward through the undulating Umbrian countryside where ancient oak forests give way to fields of barley and sunflowers in the summer months. The region is rural and deeply rooted — tractors share the road with cyclists, and stone shrines dot the edges of quiet lanes. This land once served as a buffer zone between powerful city-states, and the castles and walled villages you pass, like Castiglione del Lago or Paciano, reflect centuries of skirmishes and shifting alliances.

Birdsong accompanies much of your ride — nightingales in spring, and in open country, the ascending whistle of the skylark. Eventually, the hills begin to rise as you approach the Tuscan border, and the architecture begins to shift subtly — more terracotta, more ochre. You arrive in Città della Pieve, dramatically perched on a ridge with commanding views over the Val di Chiana. This town gave birth to Pietro Vannucci, known as Perugino, a master of Renaissance fresco and Raphael’s mentor. Walking its narrow streets is like slipping into a painted scene — ochre-brick alleys, hand-crafted archways, and a timeless view across wooded hills bathed in gold.

Day 3: Città della Pieve to Leonina

Crossing fully into Tuscany, today’s ride brings you into the surreal and sculpted terrain of the Crete Senesi. These aren’t the rolling hills of tourist postcards — this is a wilder, more elemental version of Tuscany. The clay-rich soil forms ridges and gullies that glow silver under the sun and blush red at dusk. Fields of wheat ripple like water in the wind, and solitary cypress trees stand like sentinels on distant hilltops. This area is also a haven for wildlife: foxes dart across empty roads at dawn, and kestrels hover above as they hunt in the fields.

The route dips and curves through hamlets barely touched by modern life. Around every corner, you may find a rustic farmhouse, a roadside shrine, or an abandoned villa overtaken by vines. It’s a meditative ride — one where the silence is broken only by the rustle of grain or the call of a cuckoo. Leonina is a small cluster of buildings near Asciano, where time seems to have stopped. In medieval times, this region lay on the fault line between Siena and Florence’s territorial ambitions. The fortified buildings here once served as refuge for peasants and soldiers alike. Today, they welcome travelers with stunning views and a sky that stretches forever.

Day 4: Leonina to Panzano via Siena

The day begins with soft climbs through olive groves and past fields dotted with red poppies, leading you into one of Italy’s great treasures — Siena. Entering this beautifully preserved medieval city feels like stepping into the 14th century. Its shell-shaped Piazza del Campo is where the Palio horse race is held twice a year — a chaotic, bareback sprint that pits Siena’s neighborhoods against each other in a centuries-old contest of pride. Siena was once a fierce rival of Florence, and that rivalry helped shape everything from banking to art. Its buildings reflect wealth, ambition, and gothic elegance.

From Siena, you wind into the Chianti region, where every bend in the road reveals a new postcard scene: tidy rows of Sangiovese vines, hilltop villas, and sun-warmed farmhouses made of golden stone. Wild boar roam the forests here — you may not see them, but you'll notice their presence on local menus. Your destination, Panzano, sits right in the heart of Chianti Classico. This small town has become a culinary pilgrimage site thanks to Dario Cecchini, the rockstar butcher whose passion for meat and tradition draws visitors from all over the world. The village balances high art and rustic life — a perfect Chianti paradox.

Day 5: Panzano to Impruneta via San Gimignano

This final day is a journey through Tuscany’s greatest hits — beginning with a detour west to San Gimignano, the famous town of towers. In the 13th century, over 70 towers pierced its skyline as wealthy families competed to build ever higher symbols of status. Today, 14 remain, casting long shadows over piazzas where gelato and vernaccia wine are served with the rhythm of daily life. Surrounded by vineyards and saffron fields, San Gimignano feels both theatrical and grounded — a vertical exclamation point in a landscape of curves.

Returning eastward, the road to Impruneta threads through groves of cypress and tidy terraces of olive trees. You’ll pass sleepy villages and shaded valleys where warblers and woodpeckers thrive. The air smells of pine and sun-warmed herbs. Arriving in Impruneta, you’re welcomed into a town steeped in terracotta tradition. Its kilns have supplied rooftops and architectural features for centuries, including the iconic tiles of Florence’s Duomo. Just a stone’s throw from Florence itself, Impruneta feels like a threshold between the pastoral past and the Renaissance capital. You’ve crossed regions, history, cultures — and now, with the ride behind you, all of Tuscany is in your legs.

I am so incredibly grateful to the team at Volta Pro Tours for yet another amazing life experience. If you're ever in the mood to challenge yourself to some of the most amazing cycling in Europe, reach out to Adriano and his team there. There simply is no better team in Europe for these kinds of tours. I don't have a ton of amazing life advice from my dad floating around in my head anymore, but I clearly remember him telling me years ago "If you want to get better at something, go hang out with people who are amazing at that thing. Learn from them, copy them, let them show you how it can be done." Volta and all the cyclists there completely prove my dad's point. I've never been a better rider than after hanging with these pros for a week.