Ride and Cook like a tuscan

Cooking and cycling Tuscany stile

Ride and Cook like a tuscan is, like a fine wine, has been some time in the making. Just the mention of the region conjures images of superb Renaissance art and landscapes famous for rolling hills, olive groves and cypress trees.

The many pleasures of Tuscany include tasting wine in Chianti and relaxing in the piazzas of medieval towns. Whatever you do, the combination of great art, sumptuous countryside and memorable food and wine makes a cycling trip to this enchanting part of Italy unforgettable. And if that is not enough, we have added three cooking classes to help send you home as World Class Chefs!


Day One — 28km (elevation: 551 mt)

You will check into your accommodation and then start a short warm-up bike ride. 
Today’s ride is a test ride day as it is just a taste of what is yet to come!.
We ride from the villa to San Giovanni D’Asso  famous for the white Truffle.
From there we head to Montisi, a very small and pretty medieval village now important for its olive oil.
Afterwards we ride back to our Villa through Trequanda.
Your accommodation for the entire tour will be Castello delle Serre.

Day Two — 63 km (elevation: 1.154 mt)

Today we will enjoy a nice loop ride and tonight’s first cooking class! 
Our first destination is Pienza, followed by a ride to San Giovanni D’Asso and Torrenieri
This is the only flat road for today.
From Torrenieri, we cycle to San Quirico on the old Cassia Road and part of Via Francigena.
After a break in the main square in San Quirico, we ride to Pienza. Here you can enjoy the beautiful view of the Val D’orcia valley — a UNESCO World Heritage Site.
Also here you can taste the best gelato at “Gelateria Buongusto”.
The second part of the ride is on a beautiful secondary road until Castelmuzio and Petroio village famous for their olive oil.
On the way back we’ll ride very close to Sant’Anna in Camprena, which is famous as the location for the movie: The English Patient.

Day Three — 55 km (elevation: 947 mt) 

Today could be a challenging day!
We will enjoy a guided city tour of Siena as well as the ride to Siena through a part of the Chianti area.
The Chianti area is famous for the red wine, the beautiful vineyards take us all the way to Siena.
Siena has one of Europe’s greatest medieval town squares which is linked to the historic Palio — the famous horses race.
After visiting Siena, we will drive you back to the villa.

Day Four — 65 km (elevation: 1.069 mt)

Today we will enjoy a bike ride followed by another cooking class. The loop ride today is in the middle of the Crete Senesi land.
The fist part of the ride is downhill to Asciano.
We ride through this village and immediately after we take the Lauretana road.
The first part of this road can be challenging, but the view of the hills is breathtaking.
You’ll feel as though you’re on the moon!
The second part is considered easy to moderate for our arrival in Rapolano Terme.
It is here where we will enjoy lunch and after we ride back to the villa.

Day Five — 53 km (elevation: 787 mt)

Today we will ride to Cortona as well as enjoy our third and last cooking class! 
We start from the villa and climb to Trequanda.  
This charmed land of rounded hilltops is covered with vineyards and acres of sunflowers bathed in pastel sunlight.
Feeling invigorated, we will set off on a long, slow climb towards Cortona — the delightful hill town made famous by Frances Mayes in her bestselling novel Under the Tuscan Sun.
After lunch at a local trattoria, we’ll stroll around Cortona’s pristine medieval street and then we’ll begin our descent back to the villa by van.

Day Six — 61 km (elevation: 1.107 mt)

Our last ride is to Montalcino — the famous village of Brunello wine.
Before our arrival in Montalcino, we ride through the little village of Chiusure and abbazia di Monte Oliveto, which is still a functioning monastery founded in 1313 by Bernardo Tolomei. Tolomei was a famous professor of law who later devoted his life to God at the age of 40.
After cycling on a nice secondary road mostly downhill, we’ll arrive in Buonconvento.
From here, after a good coffee, we climb to Montalcino in the middle of the vineyard of San Giovese grapes.
The way to go back to the Villa starts with a long decent from Montalcino to Torrenieri, then a flat, nice road to San Giovanni D’Asso.
From here we’ll ride UP and DOWN to the Villa.

Day Seven — Farewell

Today is our last chance to savour the scenery together before departing. 
After breakfast we will drive you back to Siena Station. 
We’re always sad to part, but we know that the friendships we made in Tuscany will continue to enrich our lives in the years ahead!

Price & Inclusions


€ 3150 per person based on double occupancy

€ 500 single supplement


6 nights’ accommodation

6 dinners, 1 lunch, 6 breakfasts

3 cooking classes

Van support, guides, snacks and refreshments

Wine, oil and cheese tastings

Not Included

Airfare to Italy, lunches, alcoholic/non-alcoholic beverages, gratuities, travel insurance, laundry expenses and items of a personal nature.

Bike rental for tour

Hybrid bicycle rental: € 210

Carbon road bicycle rental € 240

E-bike rental: € 260

Trip Details


Cooking Guided Bike Tour



Rolling hills

Best Time





Go Private

Custom groups anytime


Rapolano Terme Siena


Rapolano Terme Siena

2022 Availability

May 16-22

June 13-19

September 25 – Oct 1 FULL

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