EXPLORING TUSCANY – CHIANTI & VAL D’ORCIA
Chianti Val D’orcia Tuscany
The heart of Tuscany awaits: ride through the rolling hills of Chianti and Val d’Orcia, immerse yourself in the region’s timeless charm, unwind with exquisite local cuisine, and soak in the stunning views.
Recommended Cycling Level
★★★☆☆
In our experience, we think you will enjoy this specific tour if you are a cyclist with good bike handling skills, ability to accomplish multiple climbs of moderate grade (6-7%), the fitness to be on the bicycle for 4-5 hours a day, and the ability to ride safely with other cyclists in a line.
Cypress lined roads, both paved and limestone strade bianche, carry you from one splendid historic town to another. The climbs are short and the rewards breathtaking, photogenic, and often delicious.
Ride through beautiful Val D’ Orcia, a region untouched by time. Explore historic Bagno Vignoni, where the thermal pool has been frequented by Pope Pius II, Catherine of Siena, Lorenzo di Medici, and many artists who chose the village as a holiday destination.
Bistecca alla fiorentina, ribollita soup: Tuscan food one step from the field, simple, and delicious. Cantucci biscotti, dipped in Vin Santo, is the sweet finish to a hearty Tuscan meal. They are all on our menu.
Chianti and Montepulciano: the names of these wine regions are famous for good reason. Each provides wines with unique character, and we’ll taste their specialties as we go.
We will meet in our hotel in Radda in Chianti. We’ll get you set up on your bike and give you time to unwind and relax after your journey.
Our first ride through the Chianti region takes us through Gaiole in Chianti, a characteristic town in Tuscany, but also rated by Forbes as “the most idyllic place to live in Europe”. You will get a full understanding of the beauty of Tuscany on this very first ride. We will have lunch in a local restaurant, somewhere in the vicinity of Radda in Chianti.
Two nice climbs are the focal point of today’s ride that takes us to the walled, medieval town of Monteriggioni. We will ride through Radda in Chianti, following an undulating road up to Castellina in Chianti and a nice long descent into Monteriggioni. There we will stop for coffee and enjoy the town. On the return to Castellina in Chianti, we will embark on a climb of beautifully gentle slopes and be rewarded for our efforts with a Pizza Lunch in Castellina, before we head back to our hotel.
Today is our transfer day, leaving the Chianti region and entering Val D’Orcia. We will go by bike, passing through Siena for a coffee in the famous Piazza del Campo, and head along the Crete Senesi, a range of hills and woods with delightful villages along the way. Yes, there are hills, but nothing we can’t conquer, especially because you will be “wowed” by the views on this ride.
Today we will ride to Montepulciano and back to our hotel, taking in the unspoiled beauty of the Val D’Orcia. A ride of about 70 km, we will have one good size climb early on, then rolling hills going through Follonica and Castelluccio. With the hardest part of the ride behind us, we will take two rest breaks to partake in an espresso, a gelato, or any other local specialties. With lots of good photos, we will have plenty to talk about at dinner.
Our final day is packed with climbing. Heading towards the Vivo d’Orcia hamlet, we will climb 1000 meters along the slopes of Monte Amiata, an ancient but dormant volcano, providing an interesting backdrop to our ride. After the descent we head for the quaint village of Montalcino.
After breakfast at the hotel, we will say our goodbyes and transfer you back to the airport or train station in Florence.
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Hotel Villa Campomaggio is located in the heart of Chianti, giving guests easy access to stunning vineyards and quaint villages. This historic villa features an outdoor pool amidst lush gardens and an on-site restaurant serving genuine Tuscan cuisine. Enjoy wine tasting experiences and rustic yet modern guest rooms for a unique stay.
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Experience Hotel La Posta , set in the charming village of Bagno Vignoni, famous for its thermal springs. This historic hotel boasts a wellness center and stunning panoramic views of the Tuscan hills, perfect for relaxation after outdoor adventures. Enjoy exquisite local cuisine at the on-site restaurant, making your stay truly memorable.
CYCLING SERVICES
Local Italian guides, daily guided rides with two levels of difficulty, van support with professional mechanic, daily laundry service for your bike clothing.
PINARELLO BIKE RENTAL
Pinarello Dogma F, Pinarello Dogma X, Lombardo Garda rental included.
CYCLING GEAR
Full kit Andiamo: cycling bibs, jersey, cap, socks, summer gloves, light wind vest and arm warmers by Castelli, 2 water bottles, Rear lights, computer mount for Wahoo or Garmin, Shimano or Look pedals, Assioma power meter pedals compatible with Shimano or Look cleats (available at extra cost), Kask Protone Helmet rental (available extra at cost)
ACCOMMODATIONS
3 night at Villa Campomaggio – In the heart of the Chianti countryside, a few minutes drive from the picturesque village of Radda in Chianti.
3 nights in Hotel La Posta – in a medieval village located in the beautiful countryside of Val D’orcia.
Optional extra nights at Garda Bike Hotel in Peschiera del Garda (Lake Garda area) before or after.
DINING
Breakfast
Cycling food (sandwiches, beverages and energy supplies during rides)
Lunch in hotel or in typical restaurant during the rides – Lunch not included on arrival day
Multi-course Dinners at restaurants specializing in local cuisine – 5 Dinners included – 1 dinner NOT Included
PROGRAM FOR NON CYCLISTS
Non cyclists always enjoy breakfast, dinner and after ride special activities with partner, Regional highlights suggested
TRANSFERS
Departure collective transfer from Val d’Orcia to Florence (13th June in the morning) – On prior request, we can drop you in Bologna or Verona on our return to Peschiera
Arrival private transfer to Hotel Villa Campomaggio in Chianti, and other transfer from all the major airports of northern Italy (Florence – Milano – Venice – Bergamo) available on request, at extra charge
INSURANCE
Cancellation – Assistance – Medical expense Reimbursement – Luggage Insurance. For more info click here
OPTIONAL EXTRAS
MASSAGE: Massage Area with masseur and physiotherapist available with prior arrangement.
We stay at 4 and 5 star hotels in the best cycling location in Tuscany.
We will let you taste the dishes and the most famous wines of Tuscany.
Our guides scout and design custom routes for each day. There are 2 levels of guided rides, one for avid cyclists and one for more relaxed riders. Van support always on the rides.
Don’t bother with the hassle of packing and carrying your bike and risking damage during travel. Our luxury bike makes it easy to just show up and ride.
Size available: from 43 to 60
Group set: Shimano DURA-ACE R9270 Di2 – 12 speed electronic, hydraulic disc brakes, Chainrings DURA ACE 34 / 50, Cassette 11 / 34
Tires: Vittoria 30 mm
The DOGMA is a high-performance race bike with aggressive geometry. This bike is recommended for high level athletes who regularly ride high performance race bikes and are accustomed to the leaned over and low position, as well as the snappy handling, of this race bike.
Size available: from 43 to 60
Group set: Shimano DURA-ACE R9270 Di2 – 12 speed electronic, hydraulic disc brakes, Chainrings DURA ACE 34 / 50, Cassette 11 / 34
Tires: Vittoria 30mm
The new Pinarello Dogma X is a top of the line Pinarello road bike, with a frame designed for endurance and therefore more comfortable than the Dogma F, but still designed to be a high performing bike.
Year of the bike: 2026
Size available: 43 – 46 – 49 – 52
Weight: 16kg
Group set: Shimano GRX 1×11 speed – Chainrings 44t – Cassette 11-42t
Battery: BOSCH Compac Tube 400Wh
Saddle: Selle Royal
Handlebar & Stem: FSA AGX
Wheels: Fulcrum E-Racing 400
Tires: Vittoria 37
The Garda is a stylish and versatile e-bike designed for those who love to ride with freedom and ease.
The Bosch motor delivers smooth and quiet assistance, making every pedal stroke effortless and natural. Its comfortable geometry and modern design ensure a relaxed riding position and great control on any terrain.
Since 2005, we create cycling holidays for guests from all around the world. Our home is Garda Bike Hotel, on Lake Garda, one of the most famous bike hotel. Each year we create unique cycling experiences for over 1000 guests.
We are not a foreign agency that sells trips and outsources the management of clients to third parties. Nor are we just local cyclists, who operate without any controls. Nicola, Davide, Elisa or Alberto are always present in person with our staff at every event.
We are a certified tour operator, with all the official documentation. We are Italians and our headquarters are in italy.
We include with all our tours insurance for cancellation, assistance, medical expense, reimbursement, lost luggage. Not all tour operators include this service.
Most of our trips will run when between 3–4 people are booked. We have never cancelled a trip due to low numbers. However, there is no guarantee of this in the future. If we cancel a trip, we will give you full credit to be applied to any other one of our trips within 2 years.