Tuscany Cycling & Cooking | Food Focused | Guided Cycling Tour

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Culinary
From€3,200
Culinary
From€3,200
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Bike, Brunello & Chianti Wines plus Fiorentina Steak and an incredible Gravel Experience!

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, sometimes on gravel Backroads, and cooking lessons; we add special tastings: 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 Discover Crete Senesi, a rolling sea of land and sight-see Siena town.

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Tour Details
Informations
Tour nameTuscany Cycling & Cooking
Type of tourGuided, cycling & cooking
DeparturesScheduled or private dates
Duration6 nights, 7 days
LevelLeisure to Moderate
Total Distance213km / 132mi
Daily mileage45 to 60km / 28 to 37mi
StartPienza
EndPienza
Suggested AirportsIn / Out: Florence or Rome

Highlights:

  • Return from your trip with actual know-how to create a Tuscan dinner back home—it’s the ultimate keepsake!
  • Pedal rolling hills and Gravel Experience.
  • 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
Inclusions
Not Included
Optional Services
  • 6 nights in country house with all breakfasts
  • 6 dinners & 2 lunches
  • 2 cooking classes
  • 1 wine tour
  • 1 cheese tasting
  • Private Event on RWGPS APP, easy to follow with your own mobile
  • All Shuttles and technical assistance
  • Van support
  • Experienced English speaking guide
  • BTS reusable water bottle
  • Transfer on day 1 from Chiusi train station
  • Transfer on day 7 to Chiusi train 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
Itinerary

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

Begin your journey with a private van transfer to La Pieve di Massaini, your charming Tuscan accommodation. The villa is surrounded by vineyards, olive groves, and medicinal plants, providing the ideal setting for your adventure.
Embrace the rich heritage of the Val d’Orcia, a UNESCO World Heritage Site, and be captivated by the enchanting Palazzo Massaini, a place where quality wines, oils, and spirits are produced.

After all guest are set with bikes and equipment let’s have a very short bike ride test

At 18:00 ready for introduction total week and the chef Paolo will talk about the cooking lesson ad start with a cheese and olive oil tasting, followed by dinner at the villa.

Meals included: lunch & dinner

Day 2 Montalcino and the Art of Brunello. Distance 40 km Ascent +700m

addle up for a 40 km cycling journey that takes you through landscapes reminiscent of a Renaissance painting. First half of the ride to get to Montalcino is 80 percent gravel. Pedal through San Giovese grapes, from sangue di Giove, and visit the city bearing its name.
Montalcino medieval history is intriguing, with battles between Florentine and Sienese city-states, and a towering fortress built by the Sienese in the 14th century. Take a moment to explore Montalcino’s charming piazzas and The fortress. A gentle downhill ride awaits as you head to Castelnuovo dell’Abate to visit the Abbey of Sant’Antimo.
Enjoy a wine tour and lunch at Tenuta Fanti winery before returning to La Pieve. Two options for this: riding back for a total of 48 miles, it is a challenging but also terrific and rewarding way back. Ball in your court.
Dinner at Montefollonico at 13 gobbi – speciality tonight is Pici cacio e pepe

Meals included: breakfast, lunch & dinner

Day 3Charming Pienza! Distance 38 km Ascent +763 m.

Venture out for a 38 km bike ride that includes a visit to Pienza, the epitome of Renaissance architecture perfection by Pope Pius II.
Explore the meticulously designed Piazza Pio II, adorned with a loggia, Palazzo Piccolomini, and the impressive Duomo. As you cycle through picturesque villages like Castelmuzio, Montisi, and Trequanda on secondary paved roads. Enjoy a visit to the town and lunch on your own. Complete your journey with the last 4 km on gravel roads before returning to La Pieve.
Back to La Pieve and ready at 16:30 Ready for your first cooking session with Paolo. Hands-on lesson: prepare fresh pasta as primo piatto, after a rest with a Italian spumante metodo Classico sparkling wine as aperitif, let’s share the table with all guest and savor the dinner

Meals included: breakfast & dinner

Day 4 Siena & Le Crete & Pizza Party. Distance 47 km Ascent +672m

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.

Tonight Pizza party at villa! You can’t do a food & wine vacation in Italy without dedicating an evening to gourmet pizza Let’s sample a variety of delicious pizzas. Prepare to be surprised how great is the wine paired we selected.

Meals included: breakfast & dinner

Day 5Bagno Vignoni Spa day. Distance 28 km Ascent +387m

Embark on a bike ride to Monticchiello, a charming village with a medieval look preserved through the ages.
Make your way to Bagno Vignoni, known for its ancient healing pool.
Today a gourmet pic-nic lunch before you enjoy the thermal waters that have attracted travelers on the Via Francigena pilgrimage for centuries. Explore the healing history of this remarkable village as you wander through the streets.

Dinner at Podere il casale

Meals included: breakfast, lunch & dinner

Day 6Radicofani and the Legend of Ghino di Tacco. Distance 54 km Ascent +877m.

Today another terrific bike Cycle through gentle uphills and rolling hills, leading you to the medieval village of Radicofani. Explore the impressive fortress, offering extraordinary panoramic views over the Val d’Orcia, Amiata, the Apennines, and the Trasimeno and Bolsena lakes.
Uncover the tale of Ghino di Tacco, a charismatic gentleman bandit who roamed the Via Francigena, mentioned even in Dante’s Divine Comedy. Stroll through Radicofani’s stately old town.
Ready for another cooking lesson with chef Paolo followed by the farewell dinner? All you need is appetite & an apron!

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

Map

Rates & Dates
Guided Bike Tour
Tour Price: 3200€

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

Single occupancy: under request

2025 Departures

  • May 16 / 22 SOLD OUT
  • May 30 / 5 June CONFIRMED
  • June 6 / 12 CONFIRMED
  • June 21 /27 CONFIRMED
  • September 12 / 18 SOLD OUT
  • September 26 / 2 Oct CONFIRMED
  • October 10 / 16 CONFIRMED
  • October 24 / 30 CONFIRMED

2026 Departures

  • May 8 / 14
  • May 22 / 28
  • June 5 / 11
  • June 12 / 18
  • September 4 / 10
  • September 18 / 24
  • October 2 / 8
  • October 16 / 22

Private & Custom departures at any time

Our Bikes

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Photos
Lodging
La Pieve di Palazzo Massaini, Pienza

Far away from the noisy city life and surrounding villages, every corner of the estate offers wonderful panoramic views and enchanting atmospheres, giving a unique feeling of peace and serenity.

La Pieve di Palazzo Massaini, Pienza

The old farmhouse, carefully restored into a farmhouse, offers you an infinity pool overlooking the surrounding countryside, a private garden and common areas where you can host parties and events.
A place with a surreal atmosphere, where the rustic style of the ancient sandstone structure and the modernity of current technologies will make your stay a unique experience in authentic Tuscan style.

Reviews

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

GDPR

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