Overview
6 days / 5 nights
Experience the timeless beauty of central Italy on a cycling journey through rolling hills, medieval hilltop fortresses, and postcard-perfect cypress avenues. Riding along quiet rural roads and scenic ridge lines, you’ll connect iconic Tuscan gems including Pienza, Cortona, Montepulciano, and Siena. Beyond the handlebars, savor Tuscany’s world-renowned culinary traditions—from private tastings of Brunello and Vino Nobile di Montepulciano to artisanal pecorino cheese in Val d’Orcia. Blending rewarding rides with rich Renaissance history and exquisite lodgings, this tour captures the true spirit of la dolce vita. 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
- All 3 star accommodation
- All breakfast
- 4 full course dinners & one picnic lunch
- Winery Visits & tasting
- Private City Tour of Siena & Visit of Etruscan Tombs
- 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 Tuscan topography characterized by rolling hills, winding country roads, and short, punchy ascents into historic hilltop villages. Surfaces are predominantly smooth asphalt with brief stretches of smooth white gravel (strade bianche). Daily routes feature flexible mileage and elevation options, making it accessible for recreational riders while offering optional extra loops for ambitious cyclists. Pre-loaded GPS devices, continuous van support, and E-bike availability ensure a comfortable pace for everyone.
D1: Chiusi to Pienza (18mi) D2: Val d’Orcia & Montepulciano (28mi) D3: Montalcino Loop (32mi) D4: Cortona & Lake Trasimeno (35mi) D5: Chianti Hills & Siena (30mi) D6: San Gimignano (38mi)
Itinerary
Day 1: Chiusi to Pienza Meet in Chiusi and gear up for an introductory ride through the rolling hills of the Val d’Orcia. Pedal past cypress-lined lanes into the UNESCO-listed Renaissance village of Pienza, famous for its Pecorino cheese and sweeping valley views.
Day 2: Val d’Orcia & Montepulciano Ride through iconic Tuscan landscapes toward the hilltop jewel of Montepulciano. Explore ancient cobblestone streets, admire Renaissance palaces, and sample world-class Vino Nobile di Montepulciano at a historic underground cellar.
Day 3: Montalcino Loop Challenge yourself on rolling ridge routes heading toward Montalcino, home of Brunello wine. Enjoy spectacular views of vineyard-covered slopes, stop for a wine tasting at a local estate, and finish with a smooth descent back to your hotel.
Day 4: Cortona & Lake Trasimeno Cycle along peaceful country roads bordering Umbria and the tranquil shores of Lake Trasimeno. Climb up to the ancient Etruscan hill town of Cortona for panoramic views, historic alleyways, and local artisan shops.
Day 5: Chianti Hills & Siena Pedal into the heart of Chianti, navigating forested roads and world-famous vineyards. Stop at a historic castle or winery before coasting into Siena, where you can explore the magnificent Piazza del Campo and Gothic cathedral.
Day 6: San Gimignano & Departure Take a final scenic ride past olive groves and medieval towers into San Gimignano, known as the “Manhattan of the Middle Ages.” Celebrate an unforgettable week in Tuscany before your onward journey.