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


€ 3450 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


May 20-26

Sept/Oct 30 – 06

October 21 – 28

You may also like: Italys Tuscany bicycle region

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Based on 96 reviews
Manuel König
Manuel König
I rented the Canyon Gravel bike for the Strade Bianche and felt I had made the optimal choice. The booking process was very easy, Luigi is extremely kind, knowledgeable and helpful, the bikes are beautiful, perfectly maintained and adjusted to your needs and the price is more than fair compared to competitors. 5/5 stars. I would come back any time.
Silvia Dagnoli
Silvia Dagnoli
Top! Professionalità e disponibilità al 100%. Ho preso una Canyon Gravel a noleggio, mi sono trovata molto bene.
Very friendly, speaks good english. The bikes themselves are great. The bikes are nog insured by default.
Matthew Ng
Matthew Ng
We had 5 excellent days of gravel riding (self guided Tuscany tour). The routes that Luigi provided us were a good mix of paved and gravel, and of course hills! The bikes (Canyon Grizl) were very nice and the luggage was always waiting for us at the next hotel. Luigi was accomodating, modifying the routes based on my requests. I would definitely recommend doing a trip with this company.
Robert Head
Robert Head
The route was wonderful, with amazing scenery and history at every turn. Our guides, Sarah and Gigi were the best. They are both very accomplished and personable riders, provided interesting history of Tuscany during the tour, and emphasied safe riding while keeping everyone within sight. They are also great dinner companions!
James Twidale
James Twidale
Luigi and BikeRiding Tuscany were an absolute pleasure to deal with. The bike was in incredible condition, delivered to my hotel and Luigi even arranged for a local mechanic to help with a small mechanical issue after my first ride. The experience from start to finish was brilliant. The communication friendly and quick. Simona was equally helpful on collection of the bicycle. I would love to join Luigi for a cycle tour as he seems very knowledgeable about the area and a good rider. I would recommend this company to anyone looking to explore Tuscany or Siena.
Mark Gatha
Mark Gatha
Exceptional self guided tour. I highly recommend for all levels (but especially for a road cyclist). This is the tour company to book with! Bikes - excellent high end bikes. I rode a Canyon Ultimate CF SL Ultegra - light and fast and we'll tuned with new tires. My wife road the e-mountain bike which she really enjoyed. Routes - beautiful. We did 50-60km a day. Rapolano de Terme, Pienza, Montalcino, Siena and Castellini in Chianti. Varied terrain, vineyards, great climbs and beautiful medieval towns. Extremely well thought out. All on quiet roads. Hotels - all 3 and 4 stars with loads of character. The ones with pools were our favourites. All of the hotels were able to let us check in very early (it was hot so we rode as early as we could manage). Hotels all came with breakfast. Really great. Service - Luigi was a gem. Easy to contact, quick to communicate (before we came and during the tour) and passionate about cycling. He gave us a lot of great recommendations to help maximize our tour. I cannot say enough positive things about this trip and Bike Riding Tuscany. This was truly memorable. Highly recommended.
Bruce Jenkins
Bruce Jenkins
I was on a trip around the world and stopped in Italy. A friend recommended BikeRidingTuscany to me for an unforgettable experience and it didn’t let down. They planned a custom 1 day gravel ride for me that took us from Rapolano Terme to Sienna and back. The pace was perfect and they were gracious with any requests for breaks or stops for water/food. I enjoyed myself so much that I extended my stay to do a run on the gravel amongst the beautiful sunflowers. If you’re adventurous, and seeking some safe fun riding, this is your team
greg luckos
greg luckos
Great rental service! Nothing is a problem for Luigi. All bikes are set up tubless. Thank you

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