Hiking in Chianti: Scenic Trails Among Vineyards

Just south of Florence, the Chianti area stretches between the provinces of Florence and Siena, with rolling hills, vineyards, olive groves and small medieval villages. While best known internationally for wine production, Chianti is also a well-marked hiking destination, with routes suitable for different levels of experience.

Most trails are accessible year-round, although spring and autumn offer milder temperatures. Summer hikes should be planned early in the morning or late in the afternoon, as shade can be limited in open countryside.

Montefioralle Ring Trail

The Montefioralle ring trail is one of the most popular short hikes in Chianti. It starts near Greve in Chianti, about 30 km south of Florence, and loops around the hilltop hamlet of Montefioralle.

The route is approximately 8-10 kilometres long and takes around two hours at a relaxed pace. It follows dirt paths and secondary roads through vineyards and olive groves, with steady but manageable elevation changes.

Montefioralle itself is a small, well-preserved medieval village, with stone houses and narrow streets. The trail offers wide views over the Greve valley and surrounding hills, making it suitable for families and occasional hikers. Good walking shoes are recommended, especially after rain.

Practical information

• Distance: about 8–10 km
• Difficulty: easy to moderate
• Start/end point: Greve in Chianti (accessible by bus from Florence)
• Best seasons: spring and autumn

From Greve to Panzano

A longer and more demanding option connects Greve with Panzano in Chianti, another historic village located roughly 6 km away.

Depending on the chosen variant, the walk can range from 10 to 14 kilometres. The trail crosses sections of the Chianti Classico countryside, with gravel roads and woodland paths alternating with open vineyard landscapes.

Panzano sits on a ridge and offers panoramic views towards both the Greve valley and the Siena side of Chianti. Hikers should plan for several hours and carry water, as services along the way are limited.

Practical information

• Distance: 10–14 km
• Difficulty: moderate
• Elevation gain: significant in some stretches
• Return: same route or local bus (check seasonal timetables)

Castellina in Chianti – Castello La Leccia – Lilliano Loop

An alternative and clearly traceable option is the circular route starting from Castellina in Chianti and passing through Castello La Leccia and Lilliano, before returning to the town centre.

The itinerary develops mainly on white roads (strade bianche), vineyard tracks and secondary rural lanes typical of the Chianti Classico area. It combines open countryside views with stretches of woodland and offers wide panoramas over the surrounding hills.

The total distance is approximately 11–12 kilometres, depending on minor variations, with moderate elevation changes. The route generally takes between 3 and 4 hours at a steady walking pace.

Starting from the historic centre of Castellina, the trail descends into the countryside towards Castello La Leccia, a historic estate surrounded by vineyards, and continues towards the rural hamlet of Lilliano. From there, it gradually climbs back to Castellina.

Practical information

• Distance: about 11–12 km
• Difficulty: moderate
• Elevation gain: around 300–400 metres
• Terrain: gravel roads, dirt tracks, short paved sections
• Duration: 3–4 hours

As with most Chianti routes, shade can be limited in exposed areas. Water, sun protection and suitable footwear are recommended, particularly in warmer months. Public transport connections to Castellina are less frequent than those to Greve, so checking bus timetables in advance is advisable.

San Donato in Poggio – Olena – Cortine Loop

Near San Donato in Poggio, a small walled village between Florence and Siena, several trails explore the Pesa valley.

These routes pass through olive groves, cypress-lined roads and patches of woodland. Distances vary from short 5 km walks to longer half-day itineraries. The area is quieter than Greve and can appeal to hikers looking for less frequented paths.

Public transport is limited, so access by car is often the most practical option.

Planning a Hike in Chianti

Chianti trails are generally well signposted, often in red and white, using CAI (Italian Alpine Club) markings or local trail signs. However, carrying a map or GPS track is advisable, especially on longer routes. On apps such as Wikiloc, Komoot, Gaia GPS or Outdooractive, it is possible to find the route directly or download the trail file.

Hikers should:

• Wear proper footwear with good grip.
• Carry sufficient water.
• Check weather conditions before departure.
• Respect private property and agricultural areas, closing gates when required.

For residents and visitors in Florence, Chianti offers a combination of accessible countryside and cultural heritage. Even short hikes provide a way to explore rural Tuscany beyond the main tourist routes, within easy reach of the city.

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