This exclusive bike tour of Tuscany is fully guided by professional Italian cycling guides, includes a rental bike, and is available from April to October for private groups of four or more.  The accommodations are definitely premier level, with nothing less than 4-Star inns, and all of your breakfasts and dinners are included as well!  You’ll have a support van and luggage transfers, even your arrival and departure transfers from Florence airport.  Truly a luxury cycling holiday in one of the most classic landscapes on the planet!
Comfort Rating:
Activity Level:
7 Days

This is Tuscany, the one who we see in the movies, loved by the filmmakers.
We will ride through places that represent the quintessential Tuscany…the Chianti vineyards, cypress trees in the Val d’Orcia and the hills of Crete Senesi.  The stunning landscapes and breathtaking walled cities will require frequent stops to take photos, and the beauty of the scenery is only eclipsed by the warmth and hospitality of the Tuscan people.

Tour Dates & Pricing

Click the thumbnail to view larger image.


Day 1   Ben Venuti in Italia

Arrival in Florence at 2 PM and transfer to a charming hotel in Radda. Check in at the hotel and free afternoon to visit the old town. This evening you'll meet with our staff for a short briefing of the program. Dinner and overnight in Hotel Radda or similar.

Day 2   Radda – Greve – Panzano – Radda 

After breakfast, meeting with the guide and start of the bike tour of the heart of the Chianti. Discover the secrets of this wonderful territory between vineyards and olive trees that give flavor to your pedal! You'll leave the hotel towards the Greve, this charming town considered the capital of Chianti. Free organized lunch, photo stops, coffee and secrets of the region! Return to hotel for dinner and overnight. 

Distance: about 50 km – Ascent: 850 m (mix of descents and ascents, not a single climb)

Day 3    Radda – Castello Medievale – Gaiole in Chianti – Castello di Brolio – Radda 

After breakfast meeting with the guide before starting your daily adventure! A day of great landscapes between completely intact medieval towns! A real painting in a frame...only 21 people, 7 cats and one dog live in one of the towns you'll pass! You will make a brief pause for photos and taste the wine from the ancient recipe of Hippocrates, called ippocrasso. Then on to the town of Gaiole and the imposing Castello di Brolio.

Distance: 45 km – Ascent: 900 m (mix of descents and ascents, not a single climb)

Day 4     Radda – Val d’Orcia – Crete Senesi 

After breakfast you'll prepare for your next trip to the heart of the Val d’Orcia, chosen as the venue for several famous filmmakers, including Ridley Scott’s film “Gladiator”. Riding between wheat fields that march on like endless waves, it's easy to lose yourself in this timeless landscape. This panorama is breathtaking … The total distance is 85 km long but you are able to stop and proceed in van at the 35 km mark, or at the 50 km point. You get to choose! Dinner and overnight in Il Chiostro Hotel or similar.

Distance: 35, 50 or 85 km

Day 5    Pienza – Bagni Vignoni – San Quirico – Montalcino – Pienza 

Breakfast, meeting with the guide and at 9 AM your bike tour starts.
Today's journey epitomizes classic Tuscany, where you can admire the entire Val d’Orcia in all its splendor! You'll see one of the most famous postcards views of the cypresses San Quirico, immortalized on magazine covers all around the world! You'll even pass by the house where scenes from the movie “Gladiator” were filmed. You'll continue on, eventually arriving at Bagni Vignoni, a spa town of Roman times. In the city center is a unique rectangular pool with hot water of volcanic origin. This small village of only 30 inhabitants, will win your heart! Back in the saddle, you'll pedal on to Montalcino where there are many opportunities to experience a good glass of Brunello, one of the most famous wines in the world. After lunch return to Pienza. Dinner and overnight at Il Chiostro Hotel/similar.

Distance: 60 km – Ascent: 1000 m (mix of descents and ascents, not a single climb)

Day 6     Pienza – Monticchiello – Chianciano Terme – Montepulciano – Pienza 

Breakfast in hotel and at 9 AM the bike tour starts.Prepare your camera! You'll descend toward Montichiello, this precious medieval town where you'll briefly visit before heading on to the town of Chianciano with cinematic panoramas in all directions. In the medieval city of Montepulcino you'll take a break for lunch and free time to visit the city. Do not miss the famous Piazza Grande, where the Twilight film New Moon was shot. While here be sure to visit a wine shop for a tasting of the famous wine Nobile di Montepulciano, made with grapes grown on the surrounding hills. Dinner and overnight at Il Chiostro Hotel/similar.

Distance: 45 km – Ascent: 900 m (mix of descents and ascents, not a single climb)

Day 7     Arrivederci Italia

After breakfast private transfer to the Florence’s airport.

What´s Included

  • 3 nights in Radda, 4 * hotel with breakfast
  • 3 nights in Pienza / Montepulciano 4 * hotel with breakfast
  • 6 typical dinners
  • Rental bike
  • Minivan assistance, mineral water, cereals bars, sandwiches and fruits
  • Support for small repairs
  • Professional cycling guide for 5 days
  • Transfer from Florence airport to Radda
  • Transfer Pienza Montepulciano to Florence airport
  • Luggage transfer fom Radda to Pienza.


What´s not Included

  • Air flights
  • Lunches
  • Beverages during meals
  • Gratuities
  • Hotel room taxes (approx 1-3 Euros per day)
  • Trip Cancellation/Interruption and Medical Insurance (strongly recommended, call for details)
  • Single Supplement
  • Anything not quoted above in (see included).

Book This Trip