Tuscany Family Bike Tour
6 days
5 nights
Activity Levels 2-5
Deluxe Hotels
Tuscany Family Bike Tour
6 days
5 nights
Activity Levels 2-5
Deluxe Hotels
2026: Jul
A Taste of Italy from Pienza to Siena & Chianti
Ride from one unbelievable view to the next. Marvel at extraordinary Renaissance art and architecture. Taste delicious pecorino cheese, homemade pasta, fruity olive oils and tiramisu. Few things in this world live up to the hype. We're happy to report that everything your family has heard about Tuscany is true.
Highlights
- Experience a quintessential Tuscan vacation, biking from south to north through a beautiful rolling landscape
- Savor delectable gelato and enjoy family dinners of handmade pastas, bruschetta and other local specialties
- Explore some of the region's most celebrated towns, including Pienza, Montalcino, Siena and Radda in Chianti
- Cycle tranquil roads and lush 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 Tuscany's must-see highlights, including Pienza, a World Heritage site famous for exquisite ceramics, pecorino cheese and Renaissance architecture • Regional specialties provide the perfect fuel for rides on cypress-lined roads • Bike through southern Tuscany's rolling terrain into the Val d'Orcia • Take a family stroll on the winding streets of Montepulciano, pausing for an aperitivo or gelato on one of its hidden squares • Idle poolside 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
A sea of vineyards lines our bike route to Montalcino, a wine village where enoteche pour samples and—on a clear day—remarkable views reach as far as Siena • Leave Val d'Orcia behind as you climb up the ridgeline to enter the Crete Senesi area, where we reach an agriturismo with farm-fresh Tuscan food • Read or relax and simply take in the scene from our hotel's lovely terrace.
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
Ride past the sun-drenched chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Sienese and Florentine paintings • Sheep-dotted pastures and crumbling stone farmhouses lead to olive groves and oak woodland • Explore magnificent Siena with your family • Bike rolling hills alongside legendary Chianti Classico and Sangiovese vineyards • Discover 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)
What's Included
See moreHotels
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
Share Your Adventure!
Tag @backroadstravel or use #MyBackroadsTrip to submit your photos.
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+
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.
Please Select a Group Size
Group size is required to show per-person pricing. Your group size can be approximate and can change.