Introduction: In the Heart of Tuscany

When motorcycle travellers picture their ultimate Italian riding fantasy, they describe today’s exact route: morning light slanting through tall cypresses, sweeping curves carved into vine-clad hills, the scent of stone pines, and ancient terracotta hill towns overlooking golden valleys. Day 8 of our 15-day Twisties & The Tuscan Sun expedition brought us directly into the heart of Tuscany: from Radda in Chianti, through medieval Siena, to the Renaissance town of Pienza above the Val d’Orcia.

Waking up in Radda in Chianti felt like stepping onto a film set. The morning air at 8:00 AM carried the earthy fragrance of Sangiovese vineyards and wet stone. There is a quiet rhythm to Chianti before the day-trippers arrive—shopkeepers sweeping cobblestone doorways, locals enjoying espresso at corner bars, and twelve adventure bikes warming up ready to roll south.

Day 8 is not about chasing high mileage or mountain pass tallies; it is about pure riding poetry. The flow of the tarmac along the Strada Chiantigiana, a coffee break in Siena’s Piazza del Campo, and the cypress-lined ridge roads of the Val d’Orcia combine to create one of the most sublime riding days in Europe.

Today’s Route: From Chianti Classico to the Val d’Orcia

Our journey spanned approximately 120 miles across central Tuscany, linking three distinctive landscapes: the vineyard-covered hills of Chianti, the rolling clay swells of the Crete Senesi, and the sweeping canvas of the Val d’Orcia.

Leaving Radda in Chianti, we picked up the legendary Strada Chiantigiana (SR222)—one of Europe’s premier motorcycle roads. The SR222 weaves along the spine of the Chianti hills toward Castellina in Chianti, offering continuous third-gear sweeping bends and panoramic views over olive groves and medieval towers.

From Castellina, we descended toward Siena, parking securely outside the historic perimeter to explore Piazza del Campo on foot. Afterward, we rejoined the SR2 Cassia south into the Crete Senesi, making our final climb to Pienza via the SP146 just as the evening light turned golden across the Orcia valley.

The Ride: Vineyards, Medieval Piazza, and Cypress-Lined Curves

We rolled out from Radda in Chianti at 9:00 AM, the gentle roar of twelve engines reflecting off ancient stone walls. Joining the SR222, the riding settled into an effortless rhythm. The tarmac through Chianti is smooth and grippy, allowing you to lean smoothly through long S-bends while taking in endless rows of Sangiovese vines.

Heading toward Castellina in Chianti, morning sunbeams broke through tall cypress avenues. The road demands active focus—shifting smoothly between second and third gear and rolling on the throttle through every apex.

Every crest revealed another postcard vista: centuries-old stone farmhouses, olive groves, and distant hill castles guarding the valleys. We paused above Castellina for group photos against the rolling Chianti Classico backdrop.

After a week of touring together, our group rode with seamless cohesion, maintaining perfect formation through every Chianti corner.

By mid-morning, the roads descended gently toward Siena. We parked our bikes in a dedicated motorcycle zone outside Porta Camollia and walked through medieval alleys into the vast, shell-shaped Piazza del Campo.

At an outdoor cafe on the square, we enjoyed ice-cold espresso freddo and fresh gelato while admiring the Torre del Mangia. Taking an hour to soak in Siena’s rich history was the perfect mid-day pause.

Leaving Siena on the SR2 Cassia, lush vineyards gave way to the sun-baked clay swells of the Crete Senesi, where lone cypress trees mark distant farm entrances.

Turning onto the SP146 toward Pienza, we entered the UNESCO-listed Val d’Orcia. The late afternoon light painted the sweeping hills in rich amber hues.

The final ridge climb into Pienza offered panoramic drop-offs on both sides. As the setting sun tinged the sky in gold and violet, our twelve bikes crested the final turn into Pienza.

Rider Experiences: Reflections from the Tuscan Saddle

At our evening debrief, riders praised the balance between thrilling twisties and cultural stops. Mark (BMW R1250GS) noted: “Tuscany combines fantastic, rhythmic riding on the SR222 with incredible stops like Siena’s Piazza del Campo. It’s the ideal mix of curves and culture.”

Sarah (Ducati Multistrada) added: “Riding into Pienza at golden hour with long cypress shadows across the road was an absolute bucket-list moment. The bike felt totally locked in.”

Hotel & Evening: Sunset over Pienza and Tuscan Gastronomy

We checked into a boutique hotel just steps from Pienza’s Renaissance walls. Redesigned in the 1450s by Pope Pius II as the ‘Ideal City’, Pienza sits proudly above the Orcia valley.

From the hotel terrace, we watched the sun dip behind the rolling hills while Monte Amiata loomed on the southern horizon.

For dinner, we strolled into town for local specialities: hand-rolled pici pasta with wild boar ragù, aged Pecorino di Pienza, and Florentine steaks, paired with Chianti Classico and Brunello di Montalcino wines.

Sharing laughter and stories late into the evening, Day 8 delivered everything a Tuscan motorcycle dream tour promises.

Tomorrow: From Monte Amiata to Ancient Volterra & Lucca

Tomorrow on Day 9, we head west toward the coast and northern plains. We begin on the cool, wooded slopes of Monte Amiata—an extinct volcano with shaded hairpins—before visiting cliffside Volterra and finishing inside the walled city of Lucca.

Frequently Asked Questions: Riding Tuscany on a Motorcycle

1. What is the best time of year for a motorcycle tour in Tuscany?

May to June and September to October offer pleasant temperatures and dry roads. July brings sunny weather, though early morning starts are best to enjoy the twisties before the afternoon heat.

2. Is the Strada Chiantigiana (SR222) suitable for all motorcycle rider skill levels?

Yes. The SR222 features smooth asphalt and predictable camber, making it enjoyable for experienced cornering while remaining comfortable for intermediate riders and pillions.

3. How do you handle motorcycle parking in historic Italian cities like Siena?

Historic Italian towns enforce ZTL restricted traffic zones. Cities like Siena offer dedicated motorcycle parking bays outside the historic gates (such as Porta Camollia), letting you park securely and explore on foot.

4. What type of motorcycle is best suited for touring Tuscany’s roads?

Adventure bikes (such as the BMW R1250GS or Ducati Multistrada) and sport-touring motorcycles are ideal, offering comfortable upright seating, long fuel range, and versatile suspension.

5. Do I need an International Driving Permit (IDP) to ride a motorcycle in Italy?

UK or EU licence holders with full motorcycle entitlement generally do not need an IDP for short tourist stays, though carrying one alongside your licence and vehicle papers is always good practice.

Ready For Your Own European Adventure?

Get the full 2027 tour packs delivered to your inbox.