Tuscany Bike Tour
6 days
5 nights
Activity Levels 2-5
We rate our trips based on a range of activity levels from 1-5.
See this trip's Activity Options & Terrain for more details.
Deluxe Hotels
Tuscany Bike Tour
6 days
5 nights
Activity Levels 2-5
We rate our trips based on a range of activity levels from 1-5.
See this trip's Activity Options & Terrain for more details.
Deluxe Hotels
2026: May-Oct
A Taste of Italy from Pienza to Siena & Chianti
Bike from one unbelievable view to the next. Marvel at extraordinary Renaissance art and architecture. And savor delicious pecorino cheese, homemade pasta, fruity olive oils, and celebrated Chianti and Brunello di Montalcino wines. Few things in this world live up to the hype. We're happy to report that everything you've heard about Tuscany is true.
Highlights
- Capture a quintessential Tuscan experience, biking from south to north through a beautiful rolling landscape
- Sample fine wines in charming enoteche and dine on handmade pastas, bruschetta and other local specialties
- Explore some of the region's most iconic towns, including Pienza, Montalcino, Siena and Radda in Chianti
- Pedal peaceful roads and green hills past picturesque Brunello, Chianti Classico and Sangiovese vineyards
Start Arezzo
End Florence
* Start/End locations may vary. Do not book flights until your trip details are confirmed.
Itinerary
Days 1-2
Experience some of the region's must-see highlights, including Pienza, a World Heritage site famous for pecorino cheese, exquisite ceramics and Renaissance architecture • After a nourishing spread of Tuscan specialties, pedal cypress-lined roads through southern Tuscany's open undulating terrain into the Val d'Orcia • Montepulciano, with its winding streets and hidden squares, invites a stroll • Enjoy post-ride poolside lounging at our welcoming hotel.
Nights 1-2
Overlooking Bagno Vignoni's historic central piazza and its ancient thermal pool, Albergo Le Terme is a family-run hotel rooted in the village's long spa tradition. Comfortable rooms and inviting common spaces reflect classic Tuscan style, and the hotel's wellness area and thermal pools draw on the same underground springs that have flowed here since Roman times. (pool, spa)
Day 3
Climb by bike through a sea of vineyards to the wine village of Montalcino, where enoteche pour samples and remarkable views reach as far as Siena on a clear day • Leave Val d'Orcia behind as you climb up the ridgeline to enter Crete Senesi area, where we reach an agriturismo with farm fresh Tuscan food • Our hotel's terrace provides an idyllic venue for a sunset aperitivo.
Night 3
Set on a high ridge between the Val di Chiana and the rolling hills of the Crete Senesi near Asciano, Borgo Casabianca is a historic agricultural estate surrounded by vineyards and olive groves. Restored stone farmhouses reflect the character of a traditional Tuscan borgo, and a pool overlooking the countryside offers a peaceful place to unwind after an active day. (pool)
Days 4-6
Bike past the exposed chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine and Sienese paintings • Sun-drenched pastures dotted with sheep and crumbling stone farmhouses give way to oak woodland and olive groves • Take some time to explore Siena on your own • Ride rolling hills alongside Chianti Classico and Sangiovese vineyards • Get to know ridgetop Radda, the center of Chianti wine production • Looking for a gift? Family-owned Ceramiche Rampini offers ceramics hand-painted in the Renaissance tradition.
Nights 4-5
Set on wooded grounds in the Tuscan countryside near Castelnuovo Berardenga, Villa Curina is a tranquil 16th-century villa surrounded by cypress trees and rolling hills. Historic buildings frame an Italian-style garden, and a small chapel adorned with frescoes by Arcangelo Salimbeni reflects the property's long history. (pool)
This trip has an activity level range of 2-5
- Activity
- Activity Level
- Mileage
- Elevation
What's Included
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Hotels
Deluxe Hotels
Our Deluxe hotels have great ambience and modern comforts.
Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
Nights 1-2
*Deluxe Hotel
Overlooking Bagno Vignoni's historic central piazza and its ancient thermal pool, Albergo Le Terme is a family-run hotel rooted in the village's long spa tradition. Comfortable rooms and inviting common spaces reflect classic Tuscan style, and the hotel's wellness area and thermal pools draw on the same underground springs that have flowed here since Roman times. (pool, spa)
Night 3
*Deluxe Hotel
Set on a high ridge between the Val di Chiana and the rolling hills of the Crete Senesi near Asciano, Borgo Casabianca is a historic agricultural estate surrounded by vineyards and olive groves. Restored stone farmhouses reflect the character of a traditional Tuscan borgo, and a pool overlooking the countryside offers a peaceful place to unwind after an active day. (pool)
Nights 4-5
*Deluxe Hotel
Set on wooded grounds in the Tuscan countryside near Castelnuovo Berardenga, Villa Curina is a tranquil 16th-century villa surrounded by cypress trees and rolling hills. Historic buildings frame an Italian-style garden, and a small chapel adorned with frescoes by Arcangelo Salimbeni reflects the property's long history. (pool)
Gallery
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Bikes
Choose Your Perfect Bike
Our bikes are designed and built with specific cyclists and riding styles in mind, so we can always offer you a perfect ride. Please note that bike requests are subject to availability and prioritized based on the date they're submitted.
- $400 rental fee
- Fully internal battery with quick-swap capability for extended range
- Industry-leading Bosch drive unit with electronic shifting
- Featherweight titanium chassis
- Carbon wheels and hydraulic disc brakes
- Drop handlebars only
Min. age to ride e-bike: 16+
Included in your trip price
- Ideal for avid cyclists
- Redesigned for 2024
- Next gen titanium frame with carbon wheels
- Responsive, efficient and comfortable
- Drop handlebars only
Included in your trip price
- Lightweight titanium frame
- Lower top tubes for easier mounting and dismounting
- Upright handlebars only
- Limited availability on Unplugged Bike Tours; learn more
Min. age to ride e-bike: 16+
- $400 rental fee
- Hand-built frame features Co-Motion's custom-designed Cro-Moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train
- Custom upgraded wheelset
- Best for riders with some tandem experience.
Dates & Prices
Dates & Prices
Click on dates to see pricing, hotel or itinerary variations and to book your trip. Price is per person, double occupancy, in USD.
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