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Tuscany Bike Tours

Our Tuscany bike tour is an amazing opportunity to ride the most scenic routes in Toscana. It takes cyclists on La Foce Cypress Lined Road, a route seen in many magazines and on many Tuscany countryside paintings. Our bike trip in Tuscany also leads you on the Chiantigiana road, probably one of the most famous routes in the region. Biking in Tuscany with DIGnGO is a lifetime adventure on the gorgeous routes of the Val d’Orcia, the Val di Chiana and the Chianti.

At a glance
Duration 6 days
Starting Location Chiusi
Finishing Location Firenze
Activity Level Intermediate
Price $4,798
Sgl. Suppl. $1,200

Details of our Tuscany bike tour


Day 1: Welcome to Val di Chiana

From Montepulciano to Montepulciano (18 miles)
The Chiana Valley sets the perfect stage for a bicycle ride of a lifetime. It has wonderful orchards, olive grooves and hilltop towns. Chiana also offers wonderful views on the Val d’Orcia, so don’t forget to keep your camera handy.

Day 2: Discover Pienza

From Montepulciano to Montepulciano (35 miles)
Pienza, your destination today, is an architectural hidden gem in the Val d’Orcia. Originally called Corsignano, it is known as the ideal renaissance city and was rebuilt by Enea Silvio Piccolomini. The town of Pienza offers breathtaking views on the Val d’Orcia, so make sure to walk through the city following lunch on your own.

Day 3: Ride through the Tuscan countryside

From Montepulciano to Castelnuovo dell’Abate (28 miles)
The Tuscan countryside is one of the most photographed areas of Tuscany. It offers breathtaking views on the surrounding rolling hills and cypress lined roads. Tuscan landscapes are some of the most amazing in the world, making your bike ride even more spectacular.

Day 4: Explore Siena

From Castelnuovo dell’Abate to San Felice (34 miles)
Siena, your destination this evening, is the best town in Tuscany to get a sense of local traditions. It is famous for its local cuisine, medieval buildings and the Palio, a popular horse race. The city of Siena is simply the perfect representation of a local customs.

Day 5: Discover Chianti

From San Felice to San Felice (30 miles)
Join us for a wine tasting this evening as Chianti is one of the most internationally-recognized wine in Italy. It was awarded DOCG status in 1996 and is produced in higher quantity than any other Italian wine. Chianti Classico is definitely the most famous out of all Chianti wines and is made of at least 80% of Sangiovese grapes.

Day 6: End your trip in Florence

End of the trip
Traveling to Tuscany, Florence is definitely a city for one’s bucket list. It features some of the most famous Renaissance museums and palaces in the world: the Pitti Palace, the Ponte Vecchio, the Uffizi Gallery, the Florence Cathedral and the church of Santa Maria Novella. Firenze is a city you should take time to visit before flying to your next destination.

*The mileage refers to the basic cycling route, which is the one that 85% of our guests ride. However, we offer multiple daily bicycling routes. You may read more about those biking routes in the activity level section below or by clicking the detailed itinerary button above.


Starting date Ending date
2018-04-15 2018-04-20
2018-04-22 2018-04-27
2018-04-29 2018-05-04
Starting date Ending date
2018-05-06 2018-05-11
2018-05-13 2018-05-18
2018-05-20 2018-05-25
2018-05-27 2018-06-01
Starting date Ending date
2018-06-03 2018-06-08
2018-06-10 2018-06-15
2018-06-17 2018-06-22
2018-06-24 2018-06-29
Starting date Ending date
2018-07-01 2018-07-06
2018-07-08 2018-07-13
2018-07-15 2018-07-20
2018-07-22 2018-07-27
2018-07-29 2018-08-03
Starting date Ending date
2018-08-05 2018-08-10
2018-08-12 2018-08-17
2018-08-19 2018-08-24
2018-08-26 2018-08-31
Starting date Ending date
2018-09-02 2018-09-07
2018-09-09 2018-09-14
2018-09-16 2018-09-21
2018-09-23 2018-09-28
2018-09-30 2018-10-05
Starting date Ending date
2018-10-07 2018-10-12
2018-10-14 2018-10-19

Make a date private

Private bike tours are for those looking to travel exclusively with their group of friends. For a private biking trip choose one of our regularly schedule travel dates. You may make it exclusively for you and your friends and family or contact us to choose your own departure date. Our private bicycling tour prices are explained below:

  • An extra $500 per person for 6 – 9 guests
  • An extra $1,000 per person for 4 – 5 guests
  • An extra $2,000 per person for 2 – 3 guests


Villa Cicolina (2 nights)

Star rating: ****
Location: Montepulciano
Amenities: Pool
Member of:

Castello di Velona (1 night)

Star rating: *****
Location: Castelnuovo dell’Abate
Amenities: Pool, spa
Member of: Small Luxury Hotels of the World

Borgo San Felice (2 nights)

Star rating: *****
Location: San Felice
Amenities: Pool
Member of: Relais & Châteaux

Activity level

Biking in Tuscany provides bike riders of different ability levels an opportunity to ride the same route. Each day offers a choice of multiple bike ride options, which means that on certain days you may want to enjoy recreational cycling while on other days you may want to workout more.


Day Short option Basic option Long option
Miles Elev. Gain Miles Elev. Gain Miles Elev. Gain
1  18  1800
2  19  1800  35  3600 42 4300
3  19  2000  28  2900  38  4300
4  25  1500  34  2500  43  3500
5  17  1400  30  2600

What’s Included

  • All breakfasts, 1 lunch and 4 dinners
  • Multiples daily routes
  • The use of a fully equipped DIGnGO touring bike and gear
  • DIGnGO water bottle, helmet, Garmin GPS and saddle bag
  • 1 leader for every 5 guests
  • Snack & drinks during the day
  • Gratuities at hotels and restaurants
  • Guided tours, tastings and entrance fees as mentioned in the itinerary
  • A leader offering minivan support
  • Luggage transfers
  • Porterage
  • Minivan transfers during the trip
  • Local guides and experts
  • An email a few days prior to your trip

Types of bikes available

Touring Bike (Included)

Brand: Fuji
Model: Fuji Absolute 1.1 Disc
Weight: 10,35 kg

Road bike (Upgrade)

Brand: Scott
Model: Scott Addict Disc or similar
Weight: 8,5 kg

Electric bike (Upgrade)

Brand: Rubbee
Model: Rubbee Drive
Weight: 4.0 kg

Tour map






Castiglione d’Orcia

Poggio Rosa

Castelnuovo dell’ Abate


San Giovanni d’Asso


San Felice


Radda in Chianti

Lecchi in Chianti

Travel information

How to get to the starting location

  • Buy your flight(s) to Firenze
  • Buy your train ticket(s) from Firenze to Chiusi on www.raileurope.com
  • Make sure to check online for any timetable changes or railway company track maintenance
  • In case of a delay, please email or call your trip leaders

What to pack

We ask you to limit the number of bags you bring to 1 suitcase and 1 carry-on luggage, due to the limited space in our minivan. In order to deliver your bags to your room, we ask that each bag has a clear luggage identification tag.

What to pack for biking:

  • Padded cycling shorts
  • Cycling jersey
  • Cycling jacket
  • Bike shoes & pedals
  • Sneakers
  • Cycling gloves
  • Rain jacket
  • Cycling pants
  • Arm warmers
  • Leg warmers
  • Shoe covers & booties
  • Cycling headband or cap
  • Windbreaker
What to pack for dinner:

  • Dress pants
  •  Shirt
  •  Polo
  • Jacket but not required
  •  Dress
  •  Skirt
  • Dress pants
  • Nice top

Pre & post trip lodging options


  • JK Palace | Rates: €€€€
  • Palazzo Vecchietti | Rates: €€€€€
  • Portraite Firenze | Rates: €€€€€
  • Helvetia & Bristol | Rates: €€€
  • 1865 Residenza D’Epoca | Rates: €€
  • Antica Torre Tornabuoni | Rates: €€€
  • Hotel Unicorno | Rates: €
  • Hotel Alba Palace | Rates: €
  • Hotel Bretagna | Rates: €

  • Villa Il Patriarca | Rates: €
  • La Locanda Di Cetona | Rates: €
  • Hotel Vannucci | Rates: €

Room rate guide:

0 to 100€: €

101€ to 200€: €€

201€ to 300€: €€€

301€ to 400€: €€€€

401€ to 900€: €€€€€



January February March April May June
High F 55 57 61 65 75 82
Low F 37 37 41 44 52 58
Prec. (In) 1.3 1.3 1.4 1.8 1.4 1.5
July August September October November December
High F 88 88 80 72 62 55
Low F 63 65 58 53 45 39
Prec. (In) 0.8 1.0 3.9 2.5 4.5 3.2

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