Classical Tuscany (Florence, Chianti, Siena)

Classical Tuscany (Florence, Chianti, Siena)

Italy » Self-guided (independent) hiking tours

  • Medieval hilltop villages (incl. UNESCO sites)
  • Old castles, monasteries and churches
  • Siena - the best preserved medieval city in Europe
  • jan
  • feb
  • mar
  • apr
  • may
  • jun
  • jul
  • aug
  • sep
  • oct
  • nov
  • dec

From 665 €

Duration (days): 8

Difficulty grade:  


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This is the Tuscany that you always have dreamt of - a charmed land, equally blessed by the genius of man and nature, and often by the combined efforts of both. Think of the vineyards: rows of baby green vines that manage somehow to march in arrow-straight formation up the gently rolling hillsides, bounded by single files of darker green cypress trees, snaking sandy roads leading to rust-colored farmhouses and moss-coated castles, symmetrically rounded hilltops surmounted by towns so homogeneous as to seem one single building. We will walk in the rolling hills very often portrayed in renaissance paintings and filmed in today’s movies, a landscape with a deep blue sky, golden ochre and lush greens. From the famous vineyards of Vino Nobile and Brunello to walled medieval and renaissance boroughs, visiting superb churches and abbeys with comfortable accommodations and typical restaurants and locandas. The trip generally runs between 150 and 600 m a.s.l.

(Note that 5-day itinerary is also available; contact us for details)

Day 1: Florence

Arrive in Florence and take a moment to breathe in the air of the Renaissance and the sweet scent of locally-produced red wine. We suggest arriving early in order to have time to look around the most famous sites if interest.
Day 2: Settignano to Fiesole
Travel uphill on a twenty-five minute city bus ride to the tranquil village of Settignano where the walk begins. On your way, pass magnificent countryside views of cypress trees, olive groves and Renaissance villas. Stroll through the delightful, charming town of Fiesole and tour its Etruscan ruins, Roman amphitheater, Roman baths and Franciscan monastery. (7km; uphill/downhill walking: 300/100m)
Day 3: Variety of hiking options (Greve in Chianti)
After breakfast - transportation to Greve in Chianti, a rustic market village in the capital of the Chianti wine producing region. Check in to your charming hotel and head over to Le Cantine di Greve where you can taste over 50 different Chianti wines. In the afternoon, walk north from the attractive main square of Greve in Chianti through the inspirational, magical landscape.
Walk A: Greve in Chianti loop via Uzzano: In the afternoon, make a round walk north of the attractive main square of Greve in Chianti, through a picture perfect landscape. From the main square a round walk starts and takes you through the Chianti Classico area passing by the Villa Calcinaia and numerous vineyards with “aziende agricole” (farms) where the prestigious Chianti wine is produced. (12km; uphill/downhill hiking: 450/450m; 3hrs)
Walk B: Greve loop via Montefioralle: Explore the wonderful surroundings through the forest, among dense wild vegetation, villas, vineyards and olive groves. You will be passing by abandoned old farms, ruins and beautiful villas before reaching the panoramic hamlet of Montefioralle.(10km; uphill/downhill hiking: 400/400m; 4hrs)
Day 4: Greve in Chianti
The walk is made up of a loop out of Panzano. You walk through the hills surrounding the village, in the classic Chianti landscape that alternates forests with vineyards, offering you the possibility to discover ancient Roman farmsteads. (12km; uphill/downhill walking: 250/400m; 4hrs)
Day 5: Monte San Michele to Radda in Chianti
After breakfast, a short car transfer takes you to the highest hill in Chianti, the Monte San Michele. Descend through a forested valley of century old chestnut trees and continue towards the stunning medieval hamlet of Volpaia, situated amongst vineyards and castles. Stop in for a glass of red at a fine enoteca, wine shop, and then continue on to Radda in Chianti. (13,6km; uphill/downhill hiking: 450/350m)
Day 6: Radda in Chianti round walk
A scenic walk around the old centre of Radda in Chianti. Stop for lunch in the lovely hamlet of Vertine and in the afternoon treat yourself to a glass of Chianti wine at Colle Bereto, a celebrated local vineyard that you encounter along the way back to Radda. (16km; uphill/downhill walking: 600/600m)
Day 7: Siena
After breakfast - transportation to the marvelous city of Siena, famous for its biannual “Palio” horse race, held in the most beautiful shell-shaped square in Europe: the Piazza del Campo. Don’t miss a visit to the Duomo, an architectural treasure, and numerous inspiring palaces. History comes alive as you meander through the narrow streets of this fantastically preserved jewel of Italy.
Day 8: Arrivederci Siena
Our services end after breakfast, however we highly recommend you to book extra nights in Siena to continue exploring the old center, exquisite museums, lush galleries and marvelous churches. A visit to the top of the bell tower is also quite a sight. If you choose to leave today, travel by local bus to Florence.

Accommodation and luggage transportation:
Day 1 & 2: Florence; Day 3 & 4: Greve in Chianti; Day 5 & 6: Radda in Chianti; Day 7: Siena. 7 nights at good 2-star inns or 3 star hotels on B&B, most of them are family run; they are all centrally located (in the days you are supposed to stay in town). Breakfast is included on all days. Luggage transfer on days 3, 5 & 7.

Price: 665 Euro
Single room supplement: 195 Euro

Solo travellers (incl. sgl room supplement): 1030 Euro

The price includes: people and luggage transfers on Day 3 and Day 7; luggage transportation on Day 5; people transfer on day 5 (from Greve in Chianti to Badiaccia); accommodation in 2-3 star hotels with en-suite facilities including breakfast; detailed roadbook and map in English; phone assistance

The price does not include: flight tickets; entrance charges; tickets for the public transport; alcohol drinks; personal expenses. Possible CITY TAX to be paid in cash on the spot (it varies depending on the city and on the hotel’s category)

Tips: The trek is available from April to the end of October. Optional services could be paid extra (additional nights, incl. Rome; transfer from Florence to Greve and from Radda to Siena; guided tours in Siena and Radda). 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. For train schedules please check: