600km through the bella vita of Tuscany. No race. Your pace.
Get the Route GuideFrom Campiglia Marittima on the Tyrrhenian coast, you ride inland through the wild Maremma, past the tuff cliffs of Pitigliano, and into the Val d'Orcia — that UNESCO landscape you've seen in a thousand photos, but never like this, from the saddle of your bike. Siena in the afternoon light. Florence after a morning through the Chianti hills. 600 km of smooth tarmac, golden October light, and village bars where the espresso is strong and nobody's in a hurry.
Leave your email and we'll let you know before registration opens. Meanwhile we send you the guide, fourteen chapters to find out if it's for you.
The loop is curated so every day brings a different world.
A hidden gem on the Tuscan coast, far from the crowds. Ancient walls, narrow streets, and the Tyrrhenian Sea on the horizon. This medieval village is the gateway to your adventure. Collect your event pack, fuel up on local cuisine, and prepare for the days ahead.
Tuscany's untamed heart. Rolling grain fields, cork oaks, and empty roads stretching toward the horizon. The southern countryside the poets wrote about, where butteri (Tuscan cowboys) still herd cattle and the air carries the scent of rosemary and sea salt. You'll pass thermal springs at Saturnia and understand why this region has been called Europe's last frontier.
The road curves around the Orbetello lagoon, where pink flamingos stand motionless in the shallows. Then comes Capalbio: a tiny walled village locals call "la piccola Atene" — little Athens. Stop for a coffee on the main square. You've earned it.
You round a curve and suddenly it's there: Pitigliano, a fortress-town rising straight from volcanic tuff cliffs, houses and rock fused into one. The streets are carved into the stone itself. Sorano, its quieter neighbor, offers the same drama with fewer crowds. Places that existed before Rome.
The climb to Radicofani is the kind you remember. Long, steady, with the Val d'Orcia unfolding below you like a map. At the top: a medieval fortress, a village of stone, and a view that stretches to Monte Amiata. One of the moments you'll think about long after the ride.
Pope Pius II dreamed of the perfect Renaissance city. He built it here. Pienza is small enough to walk in ten minutes. The main street smells of fresh pecorino. The terrace behind the Duomo drops into the Val d'Orcia. Bring your camera. You'll use it.
Fourteen towers still stand from the original seventy-two. They rise from the vineyards like stone fingers pointing at the sky. In the early morning or late afternoon light, when the crowds thin out, you'll understand why it's UNESCO-protected.
The road through Chianti is everything you imagined Tuscany would be. Rows of vines climbing the hillsides. Stone farmhouses. Cypress sentinels lining the ridges. Castellina, Greve, Panzano: villages where wine is life and the pace is slow. Stop at a cantina. No one's timing you.
You arrive from the hills, and there it is: Brunelleschi's dome rising above the city. Florence needs no introduction. But arriving by bike, legs tired, the Arno glinting in the afternoon light — that's a feeling the tour buses will never know.
Older than Rome. Volterra sits on its hilltop like it has for three thousand years, surrounded by dramatic balze (clay cliffs) and wrapped in Etruscan mystery. Alabaster artisans still work here. The views stretch forever. A fitting final stop before the coast calls you home.
● Chianti ridge, late afternoon Cappuccino in a village of stone where nobody knows you. You climb a ridge between cypresses, coast down into a hamlet for pici al ragù, then roll on as the light turns gold. Dinner is at a long table with riders you met yesterday. Wine is included without asking.
● Val d'Orcia, October light October light in the Val d'Orcia isn't poetic — it's a physical thing. Gold on the cypresses, long shadows, sheep that don't move for you. You stop not for a photo but because continuing would break something fragile.
The fact that it's not a race… you take more time for yourself, you don't hesitate to stop. If there's a beautiful landscape, we stop, we take a photo. If a terrace looks inviting, we stop, we have a drink.
It's like cycling inside a painting. Really unbelievable.
I loved the flowing route that crosses so many villages, important historic cities, but above all villages that not everyone knows. Tuscany is extremely varied and has incredibly enjoyable landscapes.
When I arrived in Florence the weather was amazing. The sun was setting, and I arrived with other riders. We all met on the terrace, looking over the beautiful city. It was a goosebumps moment.
When you arrive at the finish and the people who rode at the same pace as you are there… you become friends forever.
I felt like I wasn't on Earth anymore. Somewhere else entirely.
Take a look inside the 2025 edition and hear the opinion of the riders
On 1 November at 18:00 CET you can sign up for Tuscany Trail 2027 and add The Grand Escape Tuscany in the same checkout — a month before public registration opens. Places in the bundle are limited.
Early registration is open
Get the Route GuideRegistration runs through Bike Adventure Series, the platform behind our series. You'll need a BAS account, your card, and a couple of minutes. The full walkthrough — pricing, what's included, and the exact steps — lives on the registration page.
See how registration works
Stop when you want. For as long as you want. Take that photo in front of the cypress rows. Have a second espresso at the village bar. Chat with the rider you just met on the climb.
