cycling_in_tuscany_italy (1)

Tuscany bike tours: the hills of tuscany

from  1.120,00

From San Gimignano to Montalcino

This tour is a trip through time, from the Etruscans tombs to Romans remains, from Medieval hill towns to renaissance basilicas. It also offer a great diversity of landscapes, from the vineyards covered hills of Chianti and Brunello to the barren geometrical cypress-crested moulds of the “Crete”

  • Holiday Type
    Cycling Holidays
  • Activity Level Moderate
All about the Tuscany bike tours: the hills of tuscany.


> San Gimignano
> Visit Siena
> Buonconvento – Monte Oliveto Abbey
> Montepulciano


We transfer  your luggage

Just leave it at the reception desk with your name tag and you will find it at your next accommodation.

We book  your hotels

We will book double rooms with private bathrooms in 2* or 3* hotels orxb&b or country Inns.

We supply detailed  route notes and maps

At your choice, the route notes can be in English, Italian, French or German and GPS maps

The tour package inclusions and exclusions at a glance
What is included in this tour?Items that are included in the cost of tour price.
  • 7 Nights -3 Star Level Accommodation
  • All Breakfast and 2 Dinners
  • Luggage transfer
  • Road Book & Maps
  • GPS File available
SHARE YOUR OPINIONItems that are not included in the cost of tour price.

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  1. CHIANTI Day 1 – Arrival in Poggibonsi and Settling

    Where you will be met by our representative who will drive you to your villa in Poggibonsi.

  2. SAN GIMIGNANO Day 2 – Villa S Lucchese/ Colle Vald’Elsa/San Gimignano – Km 40

    Departing from Villa San Lucchese first you encounter Colle Val d’ Elsa and its glass blowing artisans some of which you can visit. San Gimignano with its towers will request more time and a couple of hours of window shopping before starting back to San Lucchese.

  3. CHIANTI RAOADS Villa S Lucchese /Abbadia Isola /Monteriggioni /Siena – 42 Km

    A nice day through winding Chianti roads, in a landscape of luscious, vineyards and superb wineries to end in Siena to have an icecream on one of the most famous squares in Italy: Piazza del Campo.

  4. BUONCONVENTO Day 4 – Siena /Buonconvento – Km 40

    A nice day through winding Chianti roads, while the landscape is changing from luscious, vineyards to the more linear cypress-crested hills of the “Crete” near Buonconvento. Murlo is a nice little village on your way to the nice farm where you are spending the night. In summer you will be glad to get a refreshing dip in the swimming pool or in autumn a relaxing massage and a sauna at their beauty farm.

  5. BRUNELLO LAND Day 5 – Buonconvento/Montalcino – Km 46

    Rather difficult start, with fairly steeps slopes until you reach the asphalt. Then you head for The Monte Oliveto monastery. You will spend the night in a nice hotel in Montalcino the Brunello home land.

  6. SANT’ANTIMO ABBEY Day 6 – Sant’Antimo abbey

    Enjoy this fortified town from the bastions of which you will enjoy of a 360° view. The descending trail road lead you to the beautiful and peaceful church of Sant’Antimo where you may be able to listen to Gregorian chants.Night at the same Inn in Montalcino.

  7. MONTEPULCIANO Day 7 – Montalcino/Pienza/Montepulciano – Km 45

    A very full day as from the thermal square of Bagno Vignoni, to Pienza, the renaissance jewell redesigned by the pope Pio the II to become a “liveable” town; Visit the town which is also an agricultural centre well known for pecorino cheese, and truffle production. A dirt road will take you to Montichiello a nice little village immersed in the “Crete”. you can stop ther for a nice lunch or just for a cappuccino before continuing to Motepulciano known for its “Nobile” wine.

  8. YOURS DEPARTURE Day 8 – Departure

    Transfer to Chiusi train station.

Accommodation Level


Day 1 – Poggibonsi

Day 2 – Poggibonsi

Day 3 – Siena

Day 4 – Buonconvento

Day 5 – Montalcino

Day 6 – Montalcino Loop

Day 7 – Montepulciano

What happens if I can’t walk / cycle a stage?

If you find the stage too long or if for any reason you cannot walk at all for one day, let us know the previous week and we can arrange for you to go for a short stretch or for the entire stage with the luggage transfer . In some cases a small fee will be asked and you can pay it directly to the driver.

When is the best time of year?

Generally speaking the best season is certainly from April to October; however, it varies with each stage:
– You can only cross the Alps(week 1) from June 15th to September 15th
– The Appennino mountains (week 4) are more pleasurable from mid May to the end of September
– We suggest that you avoid walking among the rice fields (week 2&3) in full summer

How does the baggage transfers work?

Every morning you leave your luggage at the reception of your accommodation, better with a name-tag and you will find it at your arrival at the next accommodation. It has to be delivered by 2pm

Do you provide GPS files for all days?

Yes, on request we can provide GPS files, but we will still supply the paper description just in case your GPS does not work!

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