Tuscany Active Gourmet | Food Focused | Guided Cycling Tour

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Bike, Brunello & Chianti Wines plus Fiorentina Steak

What about Tuscany Cycling

An amazing and unforgettable guided bike trip discovering the delicacies of the Tuscan legends: good wines and unbelievable food.

Welcome to the bike trip combining fantastic moderate rides and cooking lessons; we add special tasting: olive oil, wine and cheese. Of course is la cucina Toscana – simplicity in its purest form.

Tuscany cooks take advantage of the freshest seasonal products and tamper with their natural state as little as possible. The cooking and the cycling aspects will please anyone who has a strong interest in one or both of these great passions.

You will explore gorgeous loop rides in the beautiful val d’orcia: Pienza, Montalcino, San Quirico. Across Val di Chiana to reach Cortona, Discover Crete Senesi, a rolling sea of land and sight-see Siena town.




Tour Details
Tour name Tuscany Active Gourmet
Type of tour Guided, cycling & cooking
Departures Scheduled or private dates
Duration 6 nights, 7 days
Level Leisure to Moderate
Total Distance 213km / 132mi
Daily mileage 45 to 60km / 28 to 37mi
Start Pienza
End Pienza
Suggested Airports In / Out: Florence or Rome


  • Return from your trip with actual know-how to create a Tuscan dinner back home—it’s the ultimate keepsake!
  • Pedal rolling hills past Sangiovese vineyards
  • Enjoy Brunello wine tasting at acclaimed biodynamic and organic Winery Corte Pavone
  • Eat Hand-rolled pici pasta, pecorino cheese, olio nuovo fresh-pressed olive oil, truffles, porcini mushrooms, Chianina beef, and cinghialewild boar
  • Cycle the picture-perfect Crete Senesi, a route lined the waves of golden wheat fields and solitary cypress trees
Not Included
Optional Services
  • Six nights in country house with all breakfasts
  • Six dinners & two lunch
  • Three cooking classes
  • two wine tasting
  • All maps, trip notes and detailed route directions
  • All Shuttles and technical assistance
  • Van support
  • Experienced English speaking guide
  • BTS water bottle
  • Transfer on day one from station
  • Transfer on day seven to the station
  • Sales taxes
  • Airfare to Italy
  • Bike Rental
  • Train to Chiusi
  • 5 lunches
  • Beverages
  • Gratuities
  • Travel Insurance
  • Laundry expenses
  • Items of a personal nature
  • Pre and Post Additional Nights
  • Transfers to/from other destinations

Day 1Welcome to Val d'Orcia

Meet at Chiusi train station (a major stop on all the Rome-Florence lines) at 13.00/ 13.30
Private van transfer to the country house Palazzi del Papa , 14 km /9 miles from Pienza. Check in at your room and let’s start bike fitting session and meet your guides. After all guest are set with bikes and equipment let’s have a very short bike ride test in the valley. Ready for your first cooking session with chef Paolo – perfect way to build the team.
Hands-on lesson: prepare fresh pasta as primo piatto, appetizer, tiramisu; after a rest with a prosecco sparkling wine as aperitif, let’s share the table with all guest and savor the welcome dinner
Meals included: Dinner

Day 2 Pienza to Cortona, 45 km / 28 miles

After welcome breakfast ready to start – a short transfer by van just outside Montepulciano village to let you start the first ride with a nice gentle downhill through the vino nobile vineyards. After will be flat terrain: the Val di Chiana, once a swampy lowland, except for the final climb to reach the old town on the hill Cortona, one’s of Italy’s oldest towns. The first set of city walls were built by the Etruscans in the 4th century BC. It became famous by Frances Mayes in her bestselling book “Under the Tuscan sun” also a movie!! Stroll the winding narrow – and steep! – medieval streets for a while. Transfer back to the country house by van in the afternoon, for stronger cyclist option to ride back!
Dinner in Monticchiello at Ristorante Da Daria.
Meals included: Breakfast, Dinner

Day 3Pienza & Montepulciano. 46 km / 29 miles

Our ride today starts from the villa – First stage is Pienza, a pristine Renaissance jewel created in 1458. Pope Pius II chose the famous Florentine architect Rossellino to transform his home village of Corsignano into one of the few examples left of 15th century architecture. The main product is the pecorino the delicious pungent cheese made using only sheep milk – continue to next village Montepulciano known as the Pearl of the Sixteenth Century. After the lunch at la Porta di Bacco where our friend Andrea will show the Etruscan caves, let’s go to have a wine tour at Cantine de Ricci and explore underground wine cellar. This Cantina not only is it right in the center of town just off Piazza Grande, it had been dubbed “the most beautiful wine cellar in the world.” It is also called the Cathedral of Vino and you’ll quickly understand why. Back in the saddle last stop in the village of Monticchiello, the quintessential Tuscan hill town. Bold cypress trees line our route to the Orcia valley where you bike through the fields that inspired Renaissance painters.
Dinner at Dopolavoro at La Foce
Meals included: Breakfast, Lunch, Dinner

Day 4 Pienza to Montalcino & Brunello. 48 km / 30 miles

Our ride start from the villa: first stop after 10 km easy ride is the ancient Roman spa of Bagno Vignoni. Legend has it that Saint Catherine and Pope Pius II both bathed in the thermal waters here. It is a tiny village, water has a constant temperature of 51 degrees Celsius, at the heart of the village is the “Square of sources”, namely a rectangular tank, of 16th-century origin, which contains the original source of water that comes from the underground aquifer of volcanic origins.
Now the climb to Castiglione d’Orcia is the challenge part of the day. Once at the top enjoy a long downhill till Romanesque abbey of Sant’Antimo that dates back to the time of Charlemagne. Last effort -9 km gentle up to Montalcino – the hill town is very famous for Brunello wine made with the Sangiovese Grosso grape and aged a minimum of four years. After the visit let’s reach all together Corte Pavone winery: you will taste this biodynamic & organic Brunello wine, learn about the aging and enjoy the lunch at cellar. Back to the villa for the second Cooking lesson
Meals included: Breakfast, Dinner

Day 5Pienza to Radicofani & pici. 55 km / 34 miles

Today another terrific bike ride: start from villa reach Radicofani a medieval and enchanting village with a 1000 dating Rocca, one of the most impressive fortresses in Tuscany. Radicofani is included in the Park of val d’Orcia – Unesco site and Via Francigena (which was the main route followed by pilgrims in antiquity who went to Rome), bust still is off the beaten path – so will be the most quiet day – from Radicofani now we will reach another secluded road called le Conie and reach Bagni San Filippo Enjoy the downhill back to the valley. It rise along Francigena road near the old Spedaletto Castle, shelter for wayfarer which, in the Middle Ages, wanted to get to Rome from all over Europe, in the XV century. Castle was readapted in a granary, a real fortified farm. Back to the country house by bike
This afternoon let’s learn the classic pasta of the area: pici all’ aglione sauce and pici al ragu di chianina. Pici is a fresh spaghetti, handmade one by one.
Meals included: Breakfast, Dinner

Day 6Pienza to Siena & Le Crete. 60 km / 37,5 miles

After breakfast departure by bike from the villa. First stop is San Quirico, an Etruscan origin village with a superb example of the Italian garden: the Horti Leonini. Pass through Asciano and Le crete area, with strange rock formations and lone farmhouse flanked by twin cypress tree. Let’s pedal through vineyards and forest we’ll arrive in Siena, a medieval city with beautifully preserved Gothic architecture. The entire city of Siena was built around the Piazza del Campo. Here we’ll have time to shop while exploring the many hidden medieval walkways Go soon to visit the shell shape square where the Palio horserace is run and enjoy a free lunch on your own. Back to the country house late afternoon. Farewell dinner at restaurant la Bandita townhouse in Pienza
Meals included: Breakfast, Dinner

Day 7Arrivederci! Good bye!

After a breakfast all together there will be transfer to Chiusi train station around 10.00/11.00
On request we will arrange transfer at different time.
Meals included: Breakfast


Rates & Dates
Guided Bike Tour
Tour Price: 3200€

Price based on double accommodation, it can change according to the period.

Single occupancy: under request

2024 Departures

  • May 10 / 16
  • May 17 / 23
  • June 7 / 13
  • September 13 / 19
  • September 27 / 3 Oct
  • October 11 / 17
  • October 25 / 31

Private & Custom departures at any time

Road bike for rental


Carbon frames with Ultegra 11 speed; compact groupset.



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Electric bike for rental


The hills won’t be so hard with our new Scott E-Bikes.

Touring Hybrid bike for rental


Hybrid-Touring bikes very light to face the Italian Hills.

Cycling & Cooking in Tuscany
Podere Palazzi del Papa, Pienza

The Palazzi del Papa farmhouse was built in the thirties by the Marchesa Origo – La Foce – replacing an old inn where the Eminences used to rest when they were going through the nearby Francigena road. Furnished with rustic antiques, the country house has a warm atmosphere authentic Tuscan charm. The Agriturismo has 9 double/twin bedrooms With en suite facilities with both showers and baths

Cicling Active Gourmet bike tour
Podere Palazzi del Papa, Pienza

The Country house stands in the centre of the natural reserve of Lucciola Bella, in the heart of the Orcia valley – Unesco site since 2004. This marvelous 17th century Country house belongs to a large estate property of Nardi enzo. From the vineyards a wonderful red DOC Orcia wine is produced. Of course, it is available to be tasted for all our kind guests. They produce wine, olive oil, Chianina meat.


We had a absolutely fantastic time. I expected the riding to be great but had no idea all the rest of it the week would be so wonderful. Boscarello is beautiful, of course, but in addition Carlotta was a wonderful hostess and it was exciting to meet her father as well. The food was delicious — we’re still remembering and talking about the recipies! You and Marco were absolutely the best! All the riding details we so well thought out — we loved the restaurants and the visits. It was perfecto!! Thanks very much for everything. We really look forward to doing it again!

Don & Laura