Tuscany Family Bike Tour
Tuscany Family Bike Tour
6 days
5 nights
Activity Levels 2-5
Casual & Deluxe Hotels
2025: Jun-Jul2026: May-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
StartArezzo
EndFlorence
* 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
This enchanting family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (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
An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (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
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.
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)
Night 3
Casual Hotel
An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool)
Nights 4-5
*Deluxe Hotel
A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool)
Gallery
#MyBackroadsTrip
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.
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
- Suited for a wide range of cyclists
- Comfortable ergonomic seat
- Long wheel base adds to the bike's control and stability
- Upright handlebars only
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
- 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.
Review Snapshot
by PowerReviews
Reviewed by 3 customers
From fear of crashing to the thrill of flying
Wow. Now I've been spoiled for all other travel! I loved this biking trip in Tuscany. I loved getting to know the Tuscan hillsides intimately as well as my fellow family travelers. I felt pampered and provided for as well as physically challenged and tested. The leaders spoke perfect Italian (with one leader born in Italy) and were both professional with excellent manners as well as friendly with great interpersonal skills. Oh, how we laughed! The leaders made us all feel comfortable and at ease while at the same time planned for our every unexpected need. This trip, for me and my family, was perfection. On the first ride on day one I wondered who would find me and scrape me off the roadside when I crashed going down the hills. By day four I couldn't wait to see how fast I was going on those curvy downhill portions of road! I now feel super confident on a bike and cannot wait to get back out on the road. I loved my bike and want to buy one of the same bikes that Backroads provided for us! Thank you Backroads!
Wonderful way to do a cycling tour with our 2 20-somethings
Verified Buyer
Fantastic trip -- fantastic leaders, fantastic group - there were 8 of us (two families of four). Our first BR trip. The terrain and the area, the cycling, the food, the wine, the company, and the experiences were all just great. So many things delighted. Adjectives that come to mind: authentic and special, sincere, challenging, comfortable, hilarious, unusual, delicious, beautiful, bonding... Thank you, Backroads!
Just Book it! You won't Regret it!
This trip will make you fall in love with Tuscany! It doesn't matter if you are an avid cyclist or a occasional rider, this trip has something for everyone.
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.
Please Select a Group Size
Group size is required to show per-person pricing. Your group size can be approximate and can change.
