Tuscany Family Bike Tour
A Taste of Italy from Pienza to Siena & Chianti
Tuscany really does live up to the hype. Pedal to views that have inspired art and love, dive into Renaissance beauty and taste tradition in handmade pastas, local olive oils and celebrated wines.
We rate our trips based on a range of activity levels from 1-5.
See this trip's Activity Options & Terrain for more details.
From $4,499/person
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Snapshots from the Trip
Trip at a Glance
Highlights
- Ride Tuscany’s iconic landscapes, from cypress-lined Val d’Orcia to Crete Senesi’s rolling chalk hills and Chianti’s vineyard ridges
- Explore historic hill towns including Pienza, Montepulciano and Siena, filled with Renaissance architecture and local charm
- Sample regional flavors with pecorino tastings, farm-fresh meals and celebrated wines in Montalcino and Chianti
- Take in sweeping views on peaceful roads past Brunello, Chianti Classico and Sangiovese vineyards
- Relax in style with inviting hotels, poolside downtime and sunset aperitivo on a terrace
Sample itinerary. Trip details may vary by departure.
Start Arezzo Airport & Travel Details
- Experience must-see highlights including Pienza, a World Heritage Site famous for pecorino cheese, exquisite ceramics and Renaissance architecture
- After an abundant spread of Tuscan specialties, pedal cypress-lined roads through southern Tuscany’s undulating terrain into the famed Val d’Orcia
- Montepulciano, with its winding streets and hidden squares, invites a stroll
- Unwind after the ride with a poolside lounge at our welcoming hotel.
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)
Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
- Pedal an ascent 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 the lunar landscapes of the Crete Senesi, where we stop at an agriturismo with farm fresh Tuscan food
- Our hotel’s terrace provides an idyllic venue for a sunset aperitivo.
Night 3
Casual 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)
Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
- Bike along 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
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)
Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
End Florence Airport & Travel Details
This trip has an activity level range of 2-5
All breakfasts, 4 lunches, 4 dinners
All accommodations on your Backroads trip
All gratuities at hotels and restaurants
Expertise and services of Backroads Trip Leaders
Fully equipped Backroads titanium bike, Wahoo GPS device, helmet and accessories
Bike fitting and equipment support throughout your trip
Backroads On Trip App with route maps, elevation profiles, daily snapshots and more
Additional local guides and experts, plus equipment for included activities as detailed in your itinerary
Exclusive activities, tours and cultural experiences, as detailed in your itinerary
All luggage transfers and porterage during your trip
Snacks and beverages between meals
Private cocktail and wine receptions on the first and last nights of your trip
Choice of Backroads cycling jersey, t-shirt or hat, plus water bottle and luggage tag
Detailed Travel Planner with destination tips and pre-trip information
