Tuscany: medieval towns (Florence to Siena)

€865 per person
The classic 8-day tour version is given as itinerary and price below. Get in touch with us to check details for the 5-day version.

Undertake an exhilarating self-guided walking tour of one of the most magical regions of Italy – Tuscany. It is truly a vivid combination of beautiful landscapes, rich history, art and culture. Tuscany is not only the birthplace of the Italian Renaissance but also one of the most famous wine regions in the world. Appreciate the rustic charm of the Italian province and soak in the authentic atmosphere. Visit the famous vineyards of Vino Nobile and Brunello, walk through walled medieval and renaissance boroughs and explore magnificent churches and abbeys. Enjoy comfortable accommodations, typical restaurants and local food and wine.

  • Destination
  • Duration
    8 (5) Days I Level: 2 (of 5)
  • What is included
    Accommodation in 2/3* hotels with en-suite facilities including breakfast (upgrade hotels option possible on request; contact us for details); people and luggage transfers on Day 3, Day 5 and Day 7; detailed roadbook and map in English (incl. access to GPS tracks); emergency phone assistance
  • What is not included
    Entrance charges; tickets for the public transport. Possible CITY TAX to be paid in cash on the spot (it varies depending on the city and on the hotel’s category between 2 and 7 EUR per person per night)
  • Best period
    April, May, June, July, August, September, October
Day 1: Florence
Arrive in Florence, the cradle of the Italian Renaissance. We recommend an early arrival so you can take the time to explore the main sites of interest.
Day 2: Settignano to Fiesole (8-16 km, 3-6 hrs, +350-570m/-225-570m)
You begin your independent walking tour from the village of Settignano. A 25-minute city bus ride will take you to the starting point of today’s section of the hiking route. You will enjoy the view of the wonderful countryside and beautiful Renaissance villas on your way to the charming town of Fiesole. We recommend you explore the Etruscan ruins, Roman amphitheater, Roman baths, and the Franciscan monastery.
Day 3: Variety of hiking options (Greve in Chianti) (10-12km, 2,30-3,30 hrs, +360-425m/-355-450m)
After a healthy breakfast, you will be taken to Greve in Chianti, a rustic market village in the capital of the Chianti wine-producing region. We recommend you visit Le Cantine di Greve where you can taste a wide variety of Chianti wines. You have the following hiking options to choose from: Walk A: A roundtrip walk of Greve in Chianti loop via Uzzano. In the afternoon head north of the main square of Greve in Chianti and explore a magical landscape through the local vineyards. This self-guided walking option will take you through the Chianti Classico area and the charming Villa Calcinaia. Walk B: A circular walk of Greve via Montefioralle. This hiking option gives the opportunity to explore the surrounding area from a different perspective. You will be walking through a forest of dense vegetation accompanied by charming villas, vineyards and olive groves. Ruins and abandoned old farms will accompany you as you reach the panoramic hamlet of Montefioralle.
Day 4: Greve in Chianti (11.7 km, 4 hrs, +385m/-385m)
Today’s self-guided walking route will take you on a circular walk out of Panzano. You will stroll the surrounding hills enjoying the magnificent landscape of forests and vineyards as you explore ancient Roman farmsteads.
Day 5: Monte San Michele to Radda in Chianti (12-14km, 3-5 hrs, +510m/-670m)
After a healthy breakfast, a short transfer by car will take you to the Monte San Michele, the highest hill in Chanti. From there, you will begin walking today’s this section of your independent tour descending through a forested valley of century old chestnut trees. Advance towards the breathtaking medieval hamlet of Volpaia, situated amongst vineyards and castles. We encourage you to take a break and enjoy a glass of red wine at a local enoteca before you continue your hiking journey to Radda in Chianti.
Day 6: Radda in Chianti round walk (15.8 km, 5 hrs, +590m/-590m)
Today we have prepared a particularly scenic walk around the old centre of Radda in Chianti. We advise you to stop for lunch in the charming hamlet of Vertine and later for a glass of Chianti wine at Colle Bereto, a famous local vineyard you will walk by on the way back to Radda.
Day 7: Siena
After breakfast you will be transferred to Siena. Don’t miss the beautiful Piazza del Campo, the Duomo, and many more wonderful spots and places waiting to be explored. Have a walk through history following the narrow streets of this true jewel of Italy.
Day 8: Arrivederci Siena
Your tour ends after breakfast but we encourage you to book extra nights and explore the wonderful city of Siena. If you decide on departure today, we recommend you travel to Florence by local bus and make the necessary connections from there.


865 Euro per person in twin/dbl room
Single room & Solo Traveler supplement
Single room supplement: 325 Euro
Solo Traveler supplement: 530 Euro (incl. sgl. room supplement)
Daily departures between the beginning of April and the end of October. The walks are along small gravel roads (strade bianche), footpaths and mule tracks on hilly terrain. You will cross several small hamlets and some larger villages. Florence, Pisa and Bologna airports are flown to by both major and low cost international carriers. All three airports can be easily reached by local transport, which is affordable and offers a frequent service. From Florence airport take the direct local bus to downtown. From Pisa airport, you can take either a direct train or bus to Florence. From Bologna airport take the bus to Bologna central station, then the train to Florence. To return from Siena to Florence, the SITA-TRA.IN bus station is very close to the hotel and a bus leaves every 30 minutes. If you come with your own car, please note that the hotels we use in Florence and Siena do not have a private parking lot of their own, there are several guarded parking areas which cost approximately €20 per day.
Accommodation & luggage transportation
Selected 2-3* hotels are used in this trip (hotels upgrade option possible against supplement; check details with us): 2x nights in Florence, 2x nights in Greve in Chianti, 2x nights in Radda in Chianti, 1x night in Siena (breakfast included all days). Some of these hotels have a swimming pool and restaurant. In all the accommodation the rooms have private bathrooms and a good Italian breakfast is included each morning. The trip is on bed and breakfast basis because throughout the trip there are plenty of opportunities to taste both the outstanding local cuisine and a wide array of prestigious regional wines. Luggage transfer is included from Florence to Greve in Chianti, from Greve in Chianti to Radda in Chianti and from Radda in Chianti to Siena. You travel with your luggage from Greve to Badiaccia on Monte San Michele (start of the walk on Day 5). The supplier will continue to Radda in Chianti with the luggage.

Send an enquiry about this tour

    The reservation confirmation you will get right after placing an order only confirms that your booking is received and an agent has started working on it. It doesn't mean your tour is guaranteed! Wait to hear from us with final confirmation before booking flights or making any other arrangements, related to your holiday. The dates as listed below do not correspond with real-time availability!