13 May 2026

Cycling from the Heart of Chianti

Day Rides from Castelvecchi

Starting and ending in Castelvecchi, Radda in Chianti | Tuscany

There is a place in the Chianti that few people truly know, and that those lucky enough to find it struggle to leave. Castelvecchi is a small hamlet in the hills above Radda in Chianti, sitting at 600 metres above sea level, surrounded by vineyards and oak woods, with an 11th-century Romanesque parish church that seems to keep silent watch over the entire valley. From here, the strade bianche fan out in every direction like the spokes of a wheel — and every spoke leads somewhere extraordinary.

Setting off by bike from Castelvecchi means you’ve already won: the views are right there, traffic is almost non-existent, and the air smells of pine resin and fermenting must. All that remains is choosing a direction.

Before You Set Off: What You Need to Know

Recommended bike: The terrain around Castelvecchi is predominantly strade bianche and gravel tracks. A gravel bike is the optimal choice. A mountain bike or e-bike offers more comfort on rough surfaces, but loses some efficiency on tarmac. Road bikes are unsuitable for almost all routes here.

Starting point: The hamlet of Castelvecchi lies about 3 km from Radda in Chianti. Ample free parking is available near the parish church. Those arriving by train can alight at Castellina Scalo or Poggibonsi and reach Castelvecchi by bike (approximately 20–25 km transfer ride).

Best time to visit: May–June for wildflowers and lush colours; September–October for the grape harvest and warm autumn light. In midsummer, ride in the early morning or late afternoon to avoid the heat.

Water and supplies: Bars, a grocery shop, and drinking fountains can be found in Radda in Chianti (3 km away). Always carry enough water for the full route — the white roads are often far from any resupply point.

Bike rental: Available in Radda in Chianti and Gaiole in Chianti. Some local accommodation also provides bikes for guests.

Route 1 — The Parish Church Loop

Castelvecchi › Volpaia › Pieve di Santa Maria Novella › Castelvecchi

Distance: ~30 km | Elevation gain: ~550 m | Duration: 2.5–3.5 hours | Difficulty: ★★☆☆☆

A short loop, rich in history and views, almost entirely on gravel. Perfect as a first taste of the area or as a morning ride.

The route: From Castelvecchi, head north on a gravel track through the woods to the ridge. The descent leads to Volpaia, one of the best-preserved medieval villages in the Chianti: a cluster of stone houses around a 13th-century tower, home to a cooperative winery producing one of the most acclaimed Chianti Classicos in the denomination. It deserves a stop even just to stand quietly and take it all in. Continue west on the white road to the Pieve di Santa Maria Novella a Vigna, one of the most intact Romanesque parish churches in the area, surrounded by vineyards with not a single modern building in sight — a view that looks like it has stepped out of a 15th-century painting. The return to Castelvecchi follows a hilly track with a few punchy climbs to warm the legs.

Not to be missed: The viewpoint at Volpaia, looking out over the Val di Pesa and the distant Pratomagno ridge.

Route 2 — The Radda Classic

Castelvecchi › Radda in Chianti › Panzano in Chianti › Greve in Chianti › Castelvecchi

Distance: ~65 km | Elevation gain: ~1,100 m | Duration: 4–6 hours | Difficulty: ★★★☆☆

The go-to route for anyone wanting to tick off the most iconic spots of the Chianti Classico in a single day. A blend of gravel roads and scenic tarmac, with unmissable food stops along the way.

The route: Drop down to Radda in Chianti for a morning coffee at the square’s bar, then follow the SP 429 westward in a gentle descent toward the Val di Pesa. The first landmark is the ridge of Panzano in Chianti, reached after a roughly 6 km tarmac climb with vineyard views on both sides. Panzano is world-famous for Dario Cecchini’s butcher’s shop — on a good day you might find him reciting Dante at full volume among his customers. After lunch, descend to Greve in Chianti, the main town of the Chianti Classico, with its distinctive Piazza Matteotti and its charmingly asymmetric arcaded porticoes. From Greve, climb back east on a white road through Lucolena, a small hilltop village with a bird’s-eye view over the valley, then return to Castelvecchi through the pine and fir woods of Monte San Michele.

Recommended detour: A few kilometres from Greve stands Castello di Verrazzano, the ancestral home of explorer Giovanni da Verrazzano — the first European to sight New York Bay. The estate winery is open for visits.

Route 3 — The L’Eroica White Roads

Castelvecchi › Gaiole in Chianti › Brolio › Castelnuovo Berardenga › Castelvecchi

Distance: ~80 km | Elevation gain: ~1,500 m | Duration: 5–7 hours | Difficulty: ★★★★☆

A demanding route that partly follows the course of the legendary L’Eroica, the gran fondo on white roads that every October draws thousands of cyclists from around the world to Gaiole. Recommended for fit riders on gravel bikes.

The route: From Castelvecchi, descend toward Gaiole in Chianti on gravel tracks through the Chianti forest. Gaiole is a quiet and authentic small town, far less touristy than its neighbours, with a weekly farmers’ market worth a stop. Head south from here toward Castello di Brolio, the jewel of Chianti aristocracy: the Ricasoli family’s manor crowns its hill with battlemented towers and formal Italian gardens, with a historic winery open to visitors. Continue downhill into the woods of Castelnuovo Berardenga, the southernmost municipality of the Chianti Classico, where the landscape opens into rolling fields of wheat and sunflowers — scenery that recalls the Val d’Orcia more than the classic Chianti. The return to Castelvecchi is long and demanding, with a series of gravel climbs through the wildest and least-visited corners of the entire denomination.

Pro tip: Download the L’Eroica GPX track from Komoot before you leave. Several sections of this route overlap with the official race course.

Route 4 — The Winery Loop

Castelvecchi › Monterinaldi › San Sano › Ama › Castelvecchi

Distance: ~40 km | Elevation gain: ~700 m | Duration: 3–4 hours | Difficulty: ★★★☆☆

A moderate route designed for those who want to pair cycling with wine discovery. This loop passes through some of the most interesting estates in the Chianti Classico, all open for tastings by appointment.

The route: From Castelvecchi, head southeast on gravel toward Monterinaldi, a small estate with one of the finest panoramic views across the entire Chianti ridge. Descend into the valley toward San Sano, an almost entirely restored ghost village converted into a charming residence, with a restaurant well worth the detour. The centrepiece of the route is Castello di Ama, one of Italy’s most celebrated wineries — and not only for the wine: the estate grounds house a permanent contemporary art collection featuring works by Louise Bourgeois, Anish Kapoor, and Kiki Smith. A combination of landscape, wine, and art that is hard to find anywhere else in the world. The return to Castelvecchi follows a panoramic gravel track with views over the eastern flank of the Chianti hills.

Book ahead: Tastings at Castello di Ama are in high demand — reserve at least a week in advance, especially during high season.

Where to Eat Along the Way

  • Osteria Le Panzanelle (Lucolena, Greve in Chianti) — honest homestyle Tuscan cooking; charcuterie boards and proper ribollita
  • Ristorante di Castelvecchi (Castelvecchi) — local cuisine made with garden and farm produce, terrace overlooking the parish church
  • La Bottega di Volpaia (Volpaia) — bar, wine shop, and deli in the medieval village; ideal for a mid-morning break
  • Osteria Bel Soggiorno (San Gimignano, off-route but nearby) — for those extending the day westward

A Final Thought

Castelvecchi is not just any starting point. It is one of those places that changes the way you ride: it slows you down, makes you curious, and invites you to stop. Before you clip in, take five minutes in front of the Romanesque church. Look at the stones worn smooth by centuries, the bell tower cutting against the sky. Then set off — but keep that image with you. It will be waiting when you return, unchanged, as if no time had passed at all.

Practical information: Castelvecchi is reachable by car from Siena (35 min), Florence (55 min), and Arezzo (50 min). Free parking is available near the parish church. For information on bike rental, route maps, and winery visits, the Tourist Office in Radda in Chianti (Piazza Ferrucci) is the best local resource.