Cycling in Chianti
❖ 280-900kms ❖ 6,000m - 13,000m ❖ 7 days riding / 7 nights ❖ From 3500€
The price includes your choice of a Carbon Fibre racing frame or an E-Bike.
We have a new Italian Cycling itinerary for you in 2023. We have taken some of the best roads for cycling that we have found in the last 20+ years poking around Tuscany and created another beautiful bike tour for you.
This tour is the big brother to our other Tuscany trip, one that we love to bits, but this week is bigger and better! More riding in the heart of Chianti; Greve in Chianti, Radda and Panzano . . . to drop some names. We have great hotels, hearty Chianti wines at dinner and that same delicious Tuscan food that keeps you coming back.
We start this trip in Fiesole which overlooks Firenze and will give you a real sense of what is in store. Do you like olive groves? We have quite a few kilometers of pedalling through some middle-elevation groves. Very few cars, rolling, smooth asphalt and VIEWS!
Then on to Panzano and Radda in Chianti for two nights. The hilly rides to get here will blow you away as will some of the steep grades - sorry. That’s ok as the hotel has a Spa, where you can relax your too tyred bones (ha!). Radda is home to our choice for the second best Gelateria in Italy. See our Piedmont trip for number ONE. Or, sign up for our Piedmont bike trip as well and have taste test.
We hope you will love our two nights in the completely unknown village of Certaldo, our very own hill-top "Borgo." First noted in 1164 but the village is much older and beautifully restored. Even the Michelin Guide to Tuscany (thankfully) gives it a miss. The Certaldo Loop ride is an easy pedal to San Gimignano (or further) then roll downhill on a great Tuscan road back to your own quiet Medieval village, which is at the top of another hill, of course. But in this neck of the woods, all good things are up.
And then we leave Certaldo and make our way to Siena for the final two nights. Let us introduce you to the “best seats in Siena!” We have been cycling here since ‘98 when Jimi found these seats and has introduced many people to his secret spot. Book a trip and find out. What’s the downside?
From Siena we have a great loop ride to Asciano and back up to Siena. Yes, everything is up here as you will finally understand by trip end. But thankfully with all the ups come the downhills, and what a week of riding we have ready and waiting for you!
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Tuscany Ride Difficulty 7/10
Moderate to challenging cycling; depends on your fitness and your climbing ability, because nothing is flat in Tuscany. All rides are in the hills and if you take on the extensions you will add more climbs and elevation. Extremely rewarding rides and you will want to come back and ride another week. We have some beautiful E-Bikes for those that want to “flatten the Tuscan hills.”
Chianti cycling Itinerary
Day one: Fiesole to our hotel in the Olive Groves
A great start from Fiesole; on a hill. But not for long (only 3.4k @ 3.7%), and it’s only because the hotel was built at the bottom of the village. After that it’s all downhill to the Arno river valley and your route up (there’s that word again) to the olives. There is a 7k stretch of flat road that will be a little busy - as it is the only road. Trips starting on a Sunday morning will find less traffic. You end the day by crossing the Arno again and riding through Figline, then the easy climb up to the hotel.
57k - 80+k
Day Two: Olive Groves to Radda
Today is absolutely stunning and cycling in the heart of Chianti is the only thing on your to-do list. Five hilly routes to choose from and each ride is as beautiful as the others. The short route makes a bee-line to the hotel on a great, quiet road past a gorgeous Castello. The other routes pass near to Greve in Chianti (detour into Greve available) and through Panzano; home to one of the most famous butchers in all of Italy. You will not believe his shop! Two nights in Radda.
22k - 76+k
Day Three: Radda Loop Rides
Three routes on offer today, but some of you may want to go back and ride a different route from yesterday; it’s that good and there is so much to ride! Today our hilly cycle route takes us to Castello di Brolio. This is where the wine that the world knows as Chianti Classico was created. The Castello has been linked to the Ricasoli family since 1141. Pedal back to Radda on scenic, quiet roads and tumble into that Gelateria and Spa in Radda. Tonight’s meal is something else!
38k - 90+k
Day Four: Radda to Certaldo Alto
Three more stunning rides to choose from today. All of them take us through Castellina in Chianti which has been around since 7 BC. For those of you that have the desire, there is a small Etruscan Tomb at Monte Calvario (at 10.9k into the ride). Castellina itself is definitely worth a visit and a cafe stop. We ride through the villages of Barberino Val d’Elsa, Tavernelle Val di Pesa and Montespertoli only to end up on another quiet unpopulated road all the way to Certaldo Basso. Then of course you have to ride up to your hotel in a Castello in the medieval village of Certaldo Alto. Two nights in Certaldo.
Fyi. Today, finally has a ride profile that trends down! The ride is still hilly, but it is a nicer looking profile! We wouldn’t want to spoil you after all.
See all the daily route profiles below.
50k - 90+k
Day Five: Certaldo Loop Rides
Today we have a lovely ride to San Gimignano where you will find just about every tourist that is visiting Tuscany. You will appreciate why we do not stay here. A challenging ride extension is available to Volterra via Gambassi Terme. In San G. one can also find the World Champion Gelato maker; Dondoli. We prefer our favourite Gelaterias. But that’s not saying that you shouldn’t make up your own mind. Try the cheese and black olive gelato. Have at it.
Tremendous downhill to Certaldo Basso from San G. then you have your gelato-infused climb up to the Castello in Certaldo Alto.
30k - 96+k
Day Six: Certaldo to Siena
We ride back up to Castellina in Chianti on one of the easiest and nicest climbs in Bella Toscana. But today we meet the most traffic of the week entering and leaving Poggibonsi which is at the foot of the climb. The traffic does move slowly but your bike is nimble. We’ve never had a problem here, but there it is - you are riding in some traffic.
Two route choices today. Both take you right into the heart of Siena through a 13th century Roman gate; the Porta Camollia. Again, traffic is heavy for a couple of k, as we are entering Siena and it’s probably late afternoon. But you will have plenty of room to ride your bike and the traffic is moving very slowly. Once inside the gate, there is only the odd taxi and small bus on the cobbles. However, there may be a couple thousand Sienese pedestrians on their way home from work, so riding your bike may not be possible for the next k or so. In 20 years of riding a bike into Siena, we and our guests LOVE this section. Would we change it? Nope, never. We really hope that you will like it as well. Two nights in a vibrant Siena!
61k - 90+k
Day Seven: Siena Loop Rides
We ride south of Siena today and into the rolling farm lands and fields of Asciano. The grape vines and olive groves have disappeared only to be replaced by wheat fields and far reaching vistas. Siena and her Torre del Mangia keeps a watchful eye on you for a good deal of the hilly ride. There is an absolute stunner of a road to be ridden today. The lovely SP451 from Chiusure to Buonconvento. There’s an Abbey along the route if you need a break from the great downhill and views. The ride from Buonconvento to Siena is up as usual and our steep-ish entry is through the beautiful Porta Tufi (built in 1325). Final feast in Siena tonight as the trip sadly ends tomorrow morning. But what a feast we have planned for you! After all those hills you deserve it.
68k - 90+k
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Chianti cycling BIKE TRIP DETAILS
Starting from 3500€ per person for a group of 6 riders in shared (double) accommodation.
Hotel accommodation is in high demand here so the trip prices reflect that cost, as well as a Tuscan post-Covid price increase for hotels etc. of +30%. We've also included a Carbon Frame race bike or an E-Bike in the above price.
What's included?
7 Nights hotels and breakfasts
7 evening meals
Carbon Fibre Race bike or an E-Bike.
Custom maps
Downloadable GPS routes for your phone or Garmin.
Ride profiles
Guide.
Support Van.
Photo slideshow of your trip.
We can easily make this a shorter or longer trip. Let us know what you would like.
What's not included?
Lunches
Drinks at dinner. Hotel mini-bars.
Pre and Post trip group transfers. These can be easily arranged for your group at a reasonable price. Let us know what you would like. Some of the many options are from/to: Firenze, Firenze Airport, Pisa, or Pisa Airport.