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5 Day Cycling Holiday in San Casciano dei Bagni, Province of Siena
This listing has no upcoming availability. Check out these similar experiences

This listing has no upcoming availability. Check out these similar experiences

Wine Tasting, Truffle Hunting, and Cycling Holiday Italy

This is a journey through enchanting landscapes, in every season it's like being catapulted into a painting, and you;ll surely can't wait to see what's beyond the next curve. The trip will be entirely dedicated and focused on the five senses. You will ride on Tuscan hills around Val d'Orcia and Valdichiana, get lost in magical vineyards of Brunello and Nobile di Montepulciano, step back in the past of italian history and art, take a relaxation day in wonderful thermal baths of San Casciano dei Bagni, Bagni San Filippo or Saturnia. Have magical sensations tasting the world famous Tuscan kitchen!

Key information

  • Trip type: Self-guided
  • Lodging: Center-based
  • Terrain: Hilly with some climbs
  • Starts and ends in: San Casciano dei Bagni
  • Difficulty level: Easy (Cyclist doesn't need to have certain level of fitness, mostly flat terrain though occasionally they will ride in unpaved or hills, 10-30 miles per day), Moderate (Cyclist needs to have a good level of fitness, terrain is mostly hilly or unpaved but they will ride on flat terrain sometime,31-45 miles per day)
  • Total distance: 45 kilometers / 27 miles
  • Type of bike: Road bike
  • E-bike: Available to rent
  • Minimum 2 participants

Meet the instructors

Read more


  • 1 wine tasting tour
  • 2 hours truffle hunting
  • 1 day guided bike tour
  • 3 days of self-guided bike tour
  • Road bike or e-bike rental included
  • Daily breakfast and dinner
  • 4 nights accommodation
  • Bike storage

Skill level

  • Beginner
  • Intermediate


1 cycling days in English
The organizer also speaks: French, German, Italian, Spanish
Group size: 2-12 participants
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Check-in Time:
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You will be provided five nights of accommodation at Relais La Crocetta, a typical Tuscan country house surrounded by a private garden and an old oak forest, walking distance from the historical center of San Casciano dei Bagni.


Traditionally decorated country house rooms that are perfectly suited for individuals or couples looking to take a relaxing short break. The rooms have Wi-Fi connection, private bathroom with shower, hairdryer, and courtesy kit. It has views of either overlooking La Crocetta’s garden and the lush oak forest, pure and fizzy air.



Day 1: Arrival

Arrival at your accommodation followed by a welcome cocktail and dinner in the restaurant.

Day 2: Guided bike day

After breakfast, depart for an "easy to do" bike tour in the beautiful surroundings. Relais La Crocetta's biker Alessandro is at your disposal to suggest the best track depending on your strength or experience. Along the way, take your time for photos, to breath pure air, to enjoy unforgettable panoramas, and to eat something in the small villages you'll meet. The evening at leisure. Dinner in and overnight in Relais La Crocetta.

Day 3-5: Self-guided bike days

During these days, you are free to roam around San Casciano dei Bagni using your rental bike.

Example of a mid-difficult track

  • Starting from San Casciano, there is a 4 kilometer road to Celle very easy.
  • Before the village of Celle, turn down left to Cassia road (old Roman way to Rome), a 6 kilometer downhill till Ponte sul Rigo.
  • Now (direction Siena) you ride a flat valley road (6 to 7 kilometers) until the panel that indicate Radicofani.
  • Here starts the climb (7 kilometers) to Radicofani, beautiful view on the village and the valley.
  • Once in Radicofani, turn right to Celle / San Casciano dei Bagni, dowhill for 5 kilometers and then up to Celle for 3 kilometers with only one hard point (300 meters).
  • From Celle, 4 kilometers up and down to San Casciano dei Bagni.
  • Total distance is 45 kilometers.

Included excursions

Truffle hunting

Enjoy two hours of truffle hunting with expert "Tartufaio" and his dogs in the wonderful and suggestive hills around San Casciano. At the end of your day, you can enjoy the fruit of your harvest at the restaurant, where the staff will reveal some secrets to impress your friends upon returning from your experience.

Wine tasting

Tasting of local Tuscan wines, real gems still quite unknown but truly remarkable like the DOC Orcia, the DOC Montecucco, and the Chianti dei Colli Senesi.


Alessandro Ferrarini


This cycling holiday is located in San Casciano dei Bagni at the end of Val d'Orcia, south of Tuscany. The medieval village is very famous for the ancient thermal baths; not far from Montalcino and Montepulciano worls recognized for their wines and close to many historical sites. You can enjoy excellent food, and you will absolutely not get bored strolling along the routes off the tourist-beaten path.



  • Cycling
  • Wine tasting


  • Garden
  • Restaurant


  • Bicycle rental
  • Free bicycle
  • Free Wi-Fi
  • Hair dryer


You will be provided with daily breakfast and dinner. If you have special dietary requirements don't forget to communicate it when making the reservation.

The following meals are included:

  • Breakfast
  • Dinner

The following dietary requirement(s) are served and/or catered for:

  • Regular (typically includes meat and fish)
  • Other dietary requirements on request
If you have special dietary requirements it's a good idea to communicate it to the organiser when making a reservation

Spa treatments

Sport massages are available but must be booked at least two days in advance.

What's included

  • 4 days bike rental
  • 4 hours guided bike tour
  • 2 hours truffle hunting with expert "Tartufaio" and his dogs
  • 1 wine tasting
  • Bike storage
  • 4 nights accommodation
  • Daily breakfast
  • 4 three-course dinners

What's not included

  • Beverages
  • Bike spares and reparations
  • Bars and food supplements
  • Laundry for sports apparels (no self washing and ironing)

How to get there

We can provide you private transfer from and to your arrival airport, but we suggest to rent a car as we are in an area really reach in points of interest.

Cancellation Policy

  • A reservation requires a deposit of 100% of the total price.
  • The deposit is non-refundable, if the booking is cancelled.
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