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Tuscany Bike tours – Cycling in Tuscany

From the medieval town of Montepulciano to the town of Florence, our Tuscany bike tours are lifetime adventures through the Tuscan countryside. Bike through the Val di Chiana and participate in a wine tasting. Take a self-guided tour of Pienza. Don’t forget to try Pecorino cheese. Ride your bicycle through vineyards and olive groves. Explore Montalcino, famous for il Brunello di Montalcino before cycling the Senesi hills. Dine in Siena and taste Chianti wine. Whether enjoying the Tuscan sun or tasting Tuscany wine, bicycling in Tuscany with DIGnGO is the guarantee of a well designed itinerary.

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 tours


Day 1: Ride through the Val di Chiana followed by a wine tasting in the medieval town of Montepulciano

From Montepulciano to Montepulciano (18 miles)
Meet us at the Chiusi-Chianciano Terme train station and transfer to your hotel located on the outskirts of the medieval town of Montepulciano. Toast to the week to come with a glass of Montepulciano wine in hand. Then, get fitted on your bike and ride through the medieval city of Montefollonico, located in the Val di Chiana often referred as the Chiana Valley. Later on, a wine tasting is organised for you to learn about the wine tasting etiquette before dinner at your hotel.

Day 2: Take a self-guided tour of Pienza and try the Pecorino cheese

From Montepulciano to Montepulciano (35 miles)
Cycle through the Val d’Orcia on your way to Pienza. Originally called Corsignano, Pop Pius II was born in Pienza and decided to change the name to make it the ideal Renaissance town. Once in town, go for a self guided walk of the town and self-guided tour of the Pienza cathedral, before lunch at one of the local trattoria. You may also try Pecorino cheese also referred as Pecorino Toscano, one of the local delights before cycling back to your hotel for a wonderful activity.

Day 3: Ride through the Tuscan countryside covered with vineyards and olive groves

From Montepulciano to Castelnuovo dell’Abate (28 miles)
Today’s ride takes you cycling through the Tuscan countryside, which inspired some many Tuscan artists. Cycle down La Foce Cypress Lined Road, a route seen in many magazines, television adds and on many Tuscan countryside paintings. Ride through vineyards and vines on your way to Rocca d’Orcia. In the afternoon, bike through olives grooves. If you visit the region in late September, you might see people placing tarps under the olive trees as this is the time of the olive harvest. End the day at the Castello di Velona, a hotel with a 360-degree view on the Tuscany landscape and the surrounding vineyards.

Day 4: Today’s ride goes through Montalcino and the hills overlooking Siena

From Castelnuovo dell’Abate to San Felice (34 miles)
Leave you hotel located in Castelnuovo dell’Abate and head to Montalcino. The town is famous for its castle, the Fortezza di Montalcino as well as its wine, the Brunello di Montalcino. The Brunello red wine was awarded DOCG status in 1980. From there, cycle through the hills of the Crete Senesi. Senesi meaning is clay and the area is a range of small hills south of Siena often described as lunar due to the grey colour of the soil. Later on, arrive at your hotel the Borgo San Felice, a former medieval hamlet transformed into a luxury hotel before transferring to Siena. In the evening, your trip leaders drop you just outside the Siena city walls for an evening on your own. In town, don’t miss out on the Siena cathedral as well as the Piazza del Campo located in the historic centre of Siena.

Day 5: Cycle to the town of Chianti and taste Tuscany wine

From San Felice to San Felice (30 miles)
On today’s ride, head toward the Chianti, an area famous for the Chianti Classico. Later that morning, arrive in the town of Radda in Chianti. It is surrounded by defensive wall and as you make your way through the town, be sure the check the townhall. Back at your hotel, its time to taste wine. Tour the cellars and try different types of wines. In the evening, enjoy a gourmet dinner and toast to a great week in the Tuscany wine country with a glass of Tuscany wine in hand.

Day 6: End your itinerary under the Tuscan sun in Florence

End of the trip
Even though we know the sun of Tuscany is very pleasant, everything has got to come to an end and this is the last day of your week under the Tuscan sun. However, the good news is that even though it is the end of your itinerary in Tuscany, we have many more itineraries you can choose from for your next vacation! This morning your leaders drive you back to Florence the birthplace of Renaissance. There are about 9 million tourists visiting Florence every year and it is well worth staying a few more days if you have time.

*Please note that the mileage indicated above refers to the basic route, which is the one that 85% of our guests ride. However, we offer multiple daily routes and you may read more about it 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 tours are for those of you who are seeking to travel exclusively with their group of friends. If you would like to make your trip private, you may choose one of our regularly schedule travel dates and make it exclusively for you and your friends or family or contact us to choose your own departure date. You may read more below for private tour pricing:

  • 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

Our Tuscany bike tours are lifetime experiences designed for cyclists of all levels of ability. Each day you have a choice of multiple ride options, which means that on certain days you may want to take it easy whereas on other days you may want to challenge yourself. Whatever biking route you choose, you cycle at your own pace.


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

Due to the limited space in our minivan, we ask you to limit the number of bags you bring to 1 suitcase and 1 carry-on luggage. 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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