![Guest cycling down lone, tree-lined road.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_208_0.jpg.webp?itok=txdpV1bS)
![Four guests at dinner, talking wine with local.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_172_VAR.jpg.webp?itok=9ezu4ENz)
![Guests cycling in front of red flower bushes, hills in distance.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_018.jpg.webp?itok=XHv0TMUE)
![Bird's eye shot of Italian countryside, forests, castle, hills visible.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_120.jpg.webp?itok=9E02M5dh)
![Bird's eye shot of tree-lined road, towards small countryside house.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_126_VAR.jpg.webp?itok=XvYDvt_d)
![Guest cycling past hillside homes, yellow-flowered bushes.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_156_VAR_0.jpg.webp?itok=112DIBE-)
![Two guests walking down Italian alleyway, arms over each other's shoulders.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_185_VAR.jpg.webp?itok=fLflAdlh)
![Close-up of champagne glasses.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_194.jpg.webp?itok=_Yr8Zv7T)
![Group of guests at dinner, smiling and laughing.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_203.jpg.webp?itok=pcC8ycW1)
![Two guests on sunny, stone balcony, smiling and talking.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_246.jpg.webp?itok=ftM4LDVp)
![Shot of Italian alleyway, tall buildings.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_266.jpg.webp?itok=Surx3qIS)
![Shot of alleyway, clock tower.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_269.jpg.webp?itok=k0gPWPtP)
![Shot of painting on craggy boulder, vineyard, villa in distance.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_350_VAR.jpg.webp?itok=IRz1v7Sj)
![Close-up of decorative plates.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_393.jpg.webp?itok=Sj5j2ZEN)
![Wide shot of Brunelleschi's dome and it's surrounding city.](/sites/default/files/styles/trip_gallery_full/public/2023/TT_NHO_ST_23_001.jpg.webp?itok=RnZyc__1)
Tuscany Bike Tour
From $4,099 - $4,349 /person
6 days
5 nights
Activity Levels 2-5
Casual & Casual Plus Hotels
Tuscany Bike Tour
6 days
5 nights
Activity Levels 2-5
Casual & Casual Plus Hotels
2024: Sep-Oct 2025: May-Oct
![Guest cycling down lone, tree-lined road.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_208_0.jpg.webp?itok=txdpV1bS)
![Four guests at dinner, talking wine with local.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_172_VAR.jpg.webp?itok=9ezu4ENz)
![Guests cycling in front of red flower bushes, hills in distance.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_018.jpg.webp?itok=XHv0TMUE)
![Bird's eye shot of Italian countryside, forests, castle, hills visible.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_120.jpg.webp?itok=9E02M5dh)
![Bird's eye shot of tree-lined road, towards small countryside house.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_126_VAR.jpg.webp?itok=XvYDvt_d)
![Guest cycling past hillside homes, yellow-flowered bushes.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_156_VAR_0.jpg.webp?itok=112DIBE-)
![Two guests walking down Italian alleyway, arms over each other's shoulders.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_185_VAR.jpg.webp?itok=fLflAdlh)
![Close-up of champagne glasses.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_194.jpg.webp?itok=_Yr8Zv7T)
![Group of guests at dinner, smiling and laughing.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_203.jpg.webp?itok=pcC8ycW1)
![Two guests on sunny, stone balcony, smiling and talking.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_246.jpg.webp?itok=ftM4LDVp)
![Shot of Italian alleyway, tall buildings.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_266.jpg.webp?itok=Surx3qIS)
![Shot of alleyway, clock tower.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_269.jpg.webp?itok=k0gPWPtP)
![Shot of painting on craggy boulder, vineyard, villa in distance.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_350_VAR.jpg.webp?itok=IRz1v7Sj)
![Close-up of decorative plates.](/sites/default/files/styles/trip_gallery_full/public/2023/BTTQ_AOP_ST_22_393.jpg.webp?itok=Sj5j2ZEN)
![Wide shot of Brunelleschi's dome and it's surrounding city.](/sites/default/files/styles/trip_gallery_full/public/2023/TT_NHO_ST_23_001.jpg.webp?itok=RnZyc__1)
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
![Italy Tuscany Bike Tour map](/sites/default/files/styles/trip_page_map/public/2023/24_IT_BTTQ_0.jpg.webp?itok=jGAP-7Lc)
Start Arezzo
End Florence
* Start/End locations may vary. Do not book flights until your trip details are confirmed.
Itinerary
![](/sites/default/files/styles/itinerary_533/public/2023/BTTQ_AOP_ST_22_126_VAR.jpg.webp?itok=4gOoOLrp)
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.
![](/sites/default/files/styles/itinerary_533/public/2023/TTQ_PR_23_Albergo-le-Terme_Exterior-3.jpg.webp?itok=Q5TejNMU)
Nights 1-2
This enchanting family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa)
![](/sites/default/files/styles/itinerary_533/public/2023/BTTQ_AOP_ST_22_156_VAR_0.jpg.webp?itok=V2TIvhny)
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.
![](/sites/default/files/styles/itinerary_533/public/2023/TTI_PR_23_Borgo-Casabianca_Aerial.jpg.webp?itok=ufTe7xjA)
Night 3
An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool)
![](/sites/default/files/styles/itinerary_533/public/2023/BTTQ_AOP_ST_22_172_VAR.jpg.webp?itok=NSd55TfA)
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.
![](/sites/default/files/styles/itinerary_533/public/2024/TTI_PR_24_Villa-Curina_003.jpg.webp?itok=w34SsFI1)
![](/sites/default/files/styles/itinerary_533/public/2024/TTI_PR_24_Villa-Curina_001.jpg.webp?itok=-KsJd8sM)
![](/sites/default/files/styles/itinerary_533/public/2024/TTI_PR_24_Villa-Curina_002.jpg.webp?itok=xuMWAdQk)
![](/sites/default/files/styles/itinerary_533/public/2024/TTI_PR_24_Villa-Curina_004.jpg.webp?itok=4xAsUCPT)
![](/sites/default/files/styles/itinerary_533/public/2024/TTI_PR_24_Villa-Curina_005.jpg.webp?itok=_0NPkoUr)
Nights 4-5
A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool)
What's Included
See moreHotels
Adventure-Ready Hotels
Ideally located with ready access to trip activities, our Casual hotels are also known for their character and charm.
Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.
![](/sites/default/files/styles/itinerary_533/public/2023/TTQ_PR_23_Albergo-le-Terme_Exterior-3.jpg.webp?itok=Q5TejNMU)
Nights 1-2
Casual Hotel
This enchanting family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa)
![](/sites/default/files/styles/itinerary_533/public/2023/TTI_PR_23_Borgo-Casabianca_Aerial.jpg.webp?itok=ufTe7xjA)
Night 3
Casual Hotel
An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool)
![](/sites/default/files/styles/itinerary_533/public/2024/TTI_PR_24_Villa-Curina_003.jpg.webp?itok=w34SsFI1)
![](/sites/default/files/styles/itinerary_533/public/2024/TTI_PR_24_Villa-Curina_001.jpg.webp?itok=-KsJd8sM)
![](/sites/default/files/styles/itinerary_533/public/2024/TTI_PR_24_Villa-Curina_002.jpg.webp?itok=xuMWAdQk)
![](/sites/default/files/styles/itinerary_533/public/2024/TTI_PR_24_Villa-Curina_004.jpg.webp?itok=4xAsUCPT)
![](/sites/default/files/styles/itinerary_533/public/2024/TTI_PR_24_Villa-Curina_005.jpg.webp?itok=_0NPkoUr)
Nights 4-5
Casual Plus Hotel
A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool)
Gallery
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.
![Backroads Performance Racer 2.0](/sites/default/files/styles/whats_included/public/2023/NEW_Equipment_Bikes_Performance_2.0_600x400.jpg.webp?itok=aU_EVsVj)
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
![Backroads Touring Bike](/sites/default/files/styles/whats_included/public/2024/Equipment_Bikes_Touring_600x400.jpg.webp?itok=B5CO-eD2)
Included in your trip price
- Suited for a wide range of cyclists
- Comfortable ergonomic seat
- Long wheel base adds to the bike's control and stability
- Upright handlebars only
![Backroads Electric-Assist Bike](/sites/default/files/styles/whats_included/public/2023/Electric_Assist_Bike.jpg.webp?itok=W7NEAvmZ)
Included in your trip price
- One of the lightest e-bikes available
- Provides plenty of power and more than enough battery
- Lower top tubes for easier mounting and dismounting
- Upright handlebars only
Min. age to ride e-bike: 16+
![Co-Motion Torpedo Tandem Bike](/sites/default/files/styles/whats_included/public/2020/Equipment_Bikes_tandem_600x400.jpg.webp?itok=VUFcsPP5)
- $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 for pricing, itinerary variations (if any) and to book your trip. Price is per person, double occupancy in USD.
Looks like you’re traveling with a smaller group
Our Private Trips are best for groups of 6 or more. We suggest joining a scheduled trip.
Please Select a Group Size
Group size is required to show per-person pricing. Your group size can be approximate and can change.