Overview
8 Days / 7 Nights
Experience the captivating transition between two of central Italy’s most legendary regions as you ride from the rolling cypress hills of southern Tuscany into the lush, green heart of Umbria. Pedal along quiet, scenic backroads connecting UNESCO-listed historic towns including Chiusi, Cortona, Perugia, and Assisi. Along the way, immerse yourself in authentic Italian culture with private wine tastings of Vino Nobile and Sagrantino, farm-fresh olive oils, and regional culinary specialties. Blending rewarding ridgeline cycling with rich Etruscan history and charming lodgings, this cross-regional journey offers an unforgettable taste of central Italy on two wheels. To book this tour, contact us.
If you are interested in this tour or would like to customize these dates for your private group, please use the form below to contact us and our team will assist you.
Included
- 3 & 4 star accommodation
- All breakfast
- Four full course dinners and 1 lunch
- Winery Visits & tasting
- Tour of Orvieto's Etruscan Caves
- Bike Rental (e-bike add-on available)
- Route note, maps and marked routes
- All tour & luggage transfers & van support
- Multi-lingual guide(s)
- All entrance fees
Not Included
- Airfare
- Beverages
- Trip Insurance (recommended)
- Personal Items
- Guide Tips
Route Notes
Difficulty Level: Moderate
Expect classic central Italian topography with rolling hills, winding valley roads, and steady ascents leading up to ancient hilltop towns. Surfaces are primarily smooth asphalt with occasional stretches of quiet rural pavement. Daily routes offer flexible mileage and elevation profiles suitable for recreational cyclists, with optional extra loops for avid riders. Full van support, GPS navigation devices, and E-bike options ensure a comfortable, stress-free ride for all skill levels.
D1: Chiusi to Pienza (18mi) D2: Val d’Orcia & Montepulciano (28mi) D3: Lake Trasimeno & Cortona (35mi) D4: Perugia & Tiber Valley (32mi) D5: Assisi & Spello Ridgelines (30mi) D6: Montefalco Wine Loop (38mi)
Itinerary
Day 1: Pecorino Cheese & Strade Bianche
Ride out of Siena into the quiet countryside of sweeping wheat fields, historic Abbeys, and the dramatic, ash-gray clay hills of the crete. Follow cypress-lined roads to a 13th-century Abbey to view its famous Renaissance frescoes and enjoy lunch. Afterward, pedal past the iconic film location of The English Patient and ride into Pienza for a taste of local Pecorino cheese before settling into your 4-star 15th-century palace hotel in the medieval center.
Days 2 & 3: Spa Town & Orvieto Classico
Ride from Tuscany into rural Umbria, passing an Etruscan spa town and quiet hillside villages untouched by typical tourism. Descend through volcanic vineyards into Orvieto to taste its famous Orvieto Classico wine and admire the magnificent Gothic Duomo—the “Golden Lily of Italian Cathedrals.” Explore the town’s famous tufa cliff setting, Signorelli’s Last Judgment frescoes, and an incredible 16th-century well before retiring to your converted palace hotel in the town center.
Days 4–5: Civita di Bagnoregio, Lake Bolsena & Todi
Coast down from Orvieto along quiet country roads to Civita di Bagnoregio, the dramatic, cliffside “dying city” accessible only by footbridge. Ride into the Bolsena volcanic crater to pedal along the shores of Lago di Bolsena before returning to Orvieto to explore its underground Etruscan caves. Next, cycle past Lake Corbara into the hills for a picnic in Prodo, ending in medieval Todi—a secluded mountain town wrapped in Etruscan, Roman, and medieval walls, featuring the historic Piazza del Popolo and the grand Tempio di Santa Maria della Consolazione.
Days 6–8: Spello, Assisi, Fine Wine & Ceramics
Ride through rolling Umbrian hills past historic villages to Montefalco, “the balcony of Umbria,” to sample rare, local Sagrantino wine. Coast down into pink-stoned Spello to explore Pinturicchio’s frescoes before cycling up to Assisi—the birthplace of St. Francis—to visit the famous Basilica and Giotto’s frescoes. Continue on to Torgiano for a private wine and olive oil museum tour and tasting, then pedal to Deruta to shop at its centuries-old ceramics studio. Cap off the journey with a visit to medieval Bevagna and a farewell aperitif in the town square.