Inspiring Tuscany Bike Tour
A journey through the Soul of Italy
Rolling hills, world-class wine, and postcard-perfect towns like Pienza and San Gimignano
€ 3.490
Difficulty Level
Road Surface
Asphalt
Bike Tour in Tuscany – A journey through the Soul of Italy
Inspiring Tuscany is a curated cycling journey through the heart of Italy’s most beloved region, from the medieval charm of Cortona to the Renaissance elegance of Siena. Along the way, we explore the poetic beauty of the Val d’Orcia, the UNESCO-listed hills near Pienza, and the wine-soaked towns of Montalcino and Montepulciano.
But this tour isn’t only about the views, it’s about immersion. You’ll taste award-winning olive oils, pecorino cheeses, and world-renowned wines. You’ll cycle scenic roads that locals love and discover lesser-known villages that most travelers miss.
Designed for riders who want more than a vacation, this experience brings you into the rhythm of Tuscan life, slow, soulful, and rich in tradition.
Inspiring Tuscany is more than a bike tour; it’s a ride into the heart of Italian culture, where every pedal stroke reveals a new layer of beauty, history, and pleasure.
What is included
EXTRA SERVICES
BIKE RENTAL
Each bike is rented with the following equipment
Helmets: one size fits all
Road Bikes: 1 saddlebag
Hybrid Bikes: 1 rear bag or handlebar bag
E-bikes: 1 rear bag
Most bikes have 1 water bottle cage, some have 2
*Brand and models may vary in year or color, and an alternative bike of equal value may be provided if the preferred model is unavailable
Siena Mini Tour Package Extension
€ 489 per person, based on two people who share a double room
Single room supplement: € 248
TOUR ITINERARY
DAY BY DAY
Sept 10thArrival in Cortona: Welcome to Tuscany
Your journey begins in Cortona, the iconic hilltop town made famous by Under the Tuscan Sun and Life is Beautiful. Perched above the Chiana Valley, Cortona’s stone streets wind past artisan shops, inviting cafés, and ancient walls that offer sweeping views of the surrounding countryside, a perfect first taste of the timeless Tuscan landscape.
Upon arrival at the local train station or meeting point, you’ll be met by our team and shuttled to your charming accommodation in the heart of town. After check-in, we’ll take time to set up the bikes, making sure everything is fitted and ready for the week ahead.
There’s time to relax, explore, or enjoy a cappuccino in the piazza before gathering for a welcome dinner together, the perfect moment to meet your fellow travelers, preview the journey ahead, and savor your first bite of authentic Tuscan cuisine.
Let the beauty, flavors, and warm atmosphere of Cortona ease you into the rhythm of la dolce vita.
MEALS: Dinner included
ACCOMODATION: Villa MarsiliSept 11thLakeside Ride to Castiglion del Lago
DISTANCE: 31 miles (50 km)
ELEVATION GAIN: 1509 ft (460 m)
After breakfast, we’ll set off on a scenic 10 km ride through rolling countryside toward Castiglion del Lago, a charming village perched above Lake Trasimeno. With its medieval castle, panoramic lake views, and a vibrant historic center filled with artisan shops and cafés, it’s the perfect place to wander and soak in the relaxed Tuscan pace.
For lunch, try a traditional “tagliere” of local salumi and cheeses, or a warm plate of hand-rolled pici pasta, rustic and comforting, just like the landscape. Wine lovers can choose to visit Baldetti Winery on the return route, where a reserved tasting awaits: local wines paired with bruschetta, olive oil, and pecorino cheese, a perfect way to deepen your connection with the land you’ve been riding through.
We’ll return to Cortona with an easy 12 km ride back, offering more gentle views and golden light as the day winds down.
This evening, dinner is on your own, a chance to discover another of Cortona’s trattorias or osterias, and maybe finish with a glass of Vin Santo under the stars.
MEALS: Breakfast included
ACCOMODATION: Villa MarsiliSept 12thCortona to Pienza: A Ride Through Renaissance Tuscany
DISTANCE: 30.4 miles (49 km)
ELEVATION GAIN: 1749 ft (533 m)
Today’s journey takes you deep into the heart of Siena’s province, with a ride that flows from hilltop to valley and back again. Begin with a sweeping descent from Cortona, followed by your choice of two routes:
Opt for a shorter, more direct climb, or take the longer scenic route through the medieval streets of Montepulciano, where a stop for a glass of Vino Nobile and a walk along the ancient walls is well worth the effort. Both routes meet in Torrita di Siena, a peaceful village leading us into the final stretch toward Pienza.
Once known as Corsignano, Pienza was redesigned in the 15th century by Pope Pio II as the model Renaissance town. Its elegant central square, harmonious architecture, and sweeping views earned it UNESCO World Heritage status.
Be sure to sample the town’s famous Pecorino Toscano, whether aged and sharp or young and creamy, a true taste of the land that surrounds you.
This isn’t just a ride through rolling hills, it’s a journey through Tuscany’s cultural and historical soul.
MEALS: Breakfast included
ACCOMODATION: Hotel CorsignanoSept 13thLoop Ride to Bagno Vignoni: History & Healing Waters
DISTANCE: 19.3 miles (31 km)
ELEVATION GAIN: 1444 ft (440 m)
Today’s ride is a gentle yet deeply rewarding loop through the Orcia Valley, leading to the timeless spa village of Bagno Vignoni. Tucked near the ancient Via Francigena pilgrimage route, this unique village has drawn travelers for over two thousand years, from Roman soldiers to Renaissance popes.
At its center lies the “Square of Sources”, a striking 16th-century thermal pool fed directly by a natural volcanic spring. As you explore the cobbled streets and soak in the peaceful atmosphere, it’s easy to see why Saint Catherine of Siena and Pope Pius II found solace here.
Despite the passage of centuries, Bagno Vignoni has preserved its medieval charm, making it one of Tuscany’s most atmospheric destinations, a place where healing, history, and landscape converge.
The loop ride is shorter today, giving you time to relax, perhaps enjoy a spa treatment, or simply slow down and take in the beauty of the region.
Return to Pienza in the afternoon for a leisurely evening, your home once more for the night.
MEALS: Breakfast included
ACCOMODATION: Hotel CorsignanoSept 14th Pienza to Murlo: Riding Through the Terra di Siena
DISTANCE: 39.1 miles (63 km
ELEVATION GAIN: 2667 ft (813 m)
Today’s ride leads you through one of Tuscany’s most iconic landscapes, the UNESCO-listed hills of Siena, where earth and sky seem to blend in perfect harmony. As you pedal deeper into the countryside, you’ll notice the land shifting to rich, warm tones of brown and red , the famed “Terra di Siena”, a natural pigment once prized by Renaissance painters and sourced directly from this region.
This scenic ride is a rolling journey through soft curves and open vistas, where every hilltop seems to tell a story. Farmhouses, cypress rows, and vineyards dot the landscape as you move toward Murlo, a tiny village nestled in a sea of green.
Your destination is a welcoming countryside retreat, where Mrs. Brigida greets cyclists with heartfelt hospitality. The cozy ambiance, peaceful views, and home-cooked flavors make it the perfect place to relax after a day on the road.
Tonight, enjoy a regional dinner served at the accommodation, full of rustic tastes and seasonal ingredients, an authentic expression of the land you’ve been riding through.
MEALS: Breakfast and dinner included
ACCOMODATION: Bosco della SpinaSept 15thMurlo to Siena: A Grand Finale in the Medieval Jewel
DISTANCE: 17.4 miles (28 km)
ELEVATION GAIN: 1824 ft (556 m)
Your final ride leads you into one of Italy’s most treasured cities, Siena, a medieval masterpiece perched among rolling hills. The route may be short, but it’s rich in scenery and meaning, building anticipation as you approach this legendary destination.
At the city’s heart lies Piazza del Campo, one of Europe’s most celebrated squares, shaped like a fan and framed by graceful palazzi and the soaring Torre del Mangia. This piazza is the stage for the famous Palio horse race, held twice each summer in a riot of color, tradition, and civic pride.
But Siena’s beauty goes beyond the square. Lose yourself in narrow streets lined with artisan shops, cozy cafés, and the breathtaking Siena Cathedral, a 12th-century marvel of Romanesque-Gothic architecture adorned with intricate marble and sculpture.
This afternoon is yours to explore, shop, or simply take in the timeless elegance of the city.
If you’re traveling as part of a group, we’ll gather tonight for a farewell dinner, raising a glass to a week of cycling, discovery, and unforgettable landscapes.
MEALS: Breakfast included; farewell dinner included for groups
ACCOMODATION: Hotel Santa Caterina SienaSept 16thTime to Go: Arrivederci, Tuscany
After breakfast, we’ll arrange a group transfer to the nearby train station to connect you with your onward travel. Whether you’re heading home or continuing your Italian adventure, we hope you leave with full hearts, vivid memories, and a deeper connection to Tuscany’s beauty, rhythm, and soul.
Thank you for riding with us, until next time!
MEALS: Breakfast included
