Overview
Four days in Greve in Chianti, the market town at the heart of Chianti Classico, half an hour south of Florence. This is the most beautiful landscape of the twelve and it is not a close contest: cypress avenues, stone farmhouses on ridge lines, vineyards and olive groves folding away in every direction.
It is also the hardest riding. This is Eroica country — relentless rather than steep, with few flat kilometres anywhere. Now that the group's cycling is stronger than we first assumed, it is properly on the table, and on e-bikes it becomes a genuine joy rather than a test. Late October adds the thing that makes this exact week special: the olive harvest, and the first oil of the year pressed and poured over toasted bread while still cloudy and green.
Getting There
| Outbound | Friday 23 October — BA or Vueling, Gatwick → Florence (FLR), ~2h20; or Ryanair/easyJet to Pisa, from ~£45–85 |
| Return | Monday 26 October — Florence → Gatwick, evening, from ~£50–90 |
| Airport → Greve | Tram into Florence, then the SITA bus to Greve (~1h); or a pre-booked taxi, 40 minutes. About 5 hours door to door |
| Note | Pisa is often cheaper but adds an hour on the train to Florence first |
Day by Day
Friday 23 October — Arrive & the piazza
- Morning flight to Florence; bus or transfer south into the hills, into Greve by mid-afternoon.
- Greve's Piazza Matteotti is an odd, lovely triangular arcaded square. Antica Macelleria Falorni has been on it since 1729 — go in for finocchiona, wild boar salami and a glass.
- Late afternoon: settle in, and a first bottle of Chianti Classico on the square.
- Dinner: bistecca alla fiorentina if the group is hungry, pici with wild boar ragù if not.
Saturday 24 October — The Panzano ridge
- The classic Chianti loop and the big day: up to Montefioralle, the fortified hamlet above Greve, then along the ridge through Lamole and down to Panzano — roughly 30km with 600m of climbing.
- Tasting at Fontodi in Panzano, one of the most serious estates in the appellation, farming organically in the natural amphitheatre known as the Conca d'Oro.
- Lunch in Panzano — where Dario Cecchini, the region's famous butcher, recites Dante over the meat counter.
- Roll back down to Greve. On e-bikes this is a great day out; on muscle alone it is a proper ride.
Sunday 25 October — Olive oil & Castello di Verrazzano
- Clocks back overnight. A shorter, gentler 20km morning towards Castello di Verrazzano — the estate of the family that gave New York its bridge — for a tour of cellars, gardens and the old fattoria.
- The seasonal treat: late October is olive pressing. Estates and frantoi around Greve press through the last week of the month, and the new oil — cloudy, green, peppery — is poured over toasted bread. It is a different substance from the stuff in supermarkets.
- Afternoon option: Antinori nel Chianti Classico at Bargino, a spectacular winery buried in a hillside with a terracotta-ribbed roof you can walk over. Takes bookings all week.
- Return bikes; last dinner in Greve.
Monday 26 October — Home (via Florence)
- Morning bus down to Florence, with a couple of hours for the Duomo, the Mercato Centrale, or simply an espresso standing at a bar.
- Afternoon flight home from Florence.
Festivals & Local Events
Expo del Chianti Classico, Greve — second weekend of September
Greve's own wine fair fills the piazza with the appellation's producers. A month and a half before our weekend.
Chianti d'Autunno — through October
A programme of autumn events across the Chianti comuni including Greve — wine tastings, markets, music and art in the villages. Dates vary by village and are published locally each September.
Sagre delle castagne — October weekends
Chestnut festivals run through October in the hill villages of Tuscany, with roasted chestnuts, castagnaccio and local wine. Small, unpretentious and easy to stumble into.
Olive harvest & new oil — last week of October into November
The real seasonal event, and the reason to come this exact week. Frantoi (oil mills) run day and night; many estates offer olio nuovo tastings. Ask the hotel which local mill is pressing.
Impruneta Festa dell'Uva — last Sunday of September
A famous grape festival with rival districts building elaborate floats, half an hour north towards Florence.
The Region in Brief
A little history
The Chianti League was formed in the 13th century by Florence to defend its southern frontier against Siena; its emblem, a black rooster on a gold field, is still on every bottle of Chianti Classico. Legend has it the two cities agreed to settle the border by sending a rider from each at cockcrow, the meeting point to be the frontier — and that the Florentines starved their black cockerel so it crowed early. In 1716 Grand Duke Cosimo III defined the boundaries of the Chianti wine region by decree, making it one of the world's first legally delimited appellations, two centuries before France got round to it.
October weather
Warm and often glorious in late October: typically 10–20°C, with morning mist in the valleys burning off by mid-morning. The vine leaves turn gold and scarlet, and the light in the last week of October is the reason painters come here.
The wines
Sangiovese, and increasingly little else — Chianti Classico must now be at least 80% of it, and the best estates go to 100%. Sharp cherry fruit, dried herbs, tea leaf and firm tannin; a wine built to sit beside food rather than to be admired alone. Above it sit Gran Selezione and the neighbouring Super Tuscans; below it, the honest annata that costs a tenth as much and goes with everything.
The food
Bistecca alla fiorentina (a two-inch T-bone, served rare and shared), pici, pappardelle with wild boar, ribollita, panzanella, pecorino, and cantucci with vin santo. And in this precise week, olio nuovo — the new pressing, cloudy and peppery, on toasted bread.
Where to Stay
Villa Bordoni
A restored villa with a garden, a fine kitchen and views down the valley. The best bed near Greve.
Albergo del Chianti
Simple, central, with a small pool — walk to the butcher and the bars.
Agriturismo in the hills
Working estates with rooms, usually with their own wine and oil. Beautiful, but check the access road before booking with bikes.
The Wineries
Fontodi
One of the great Chianti Classico estates, farming organically in a natural amphitheatre. Flaccianello is among Tuscany's finest reds. Book ahead.
Castello di Verrazzano
Cellars, gardens and a historic fattoria, with polished daily tours that can include lunch. The navigator Giovanni da Verrazzano was born here.
Antinori nel Chianti Classico
A remarkable modern winery sunk into a hillside under a terracotta-ribbed roof planted with vines. 26 generations of Antinori. Bookings all week.
Montevertine
No Chianti Classico label at all by choice; Le Pergole Torte is one of Italy's greatest Sangiovese. Small, so email well ahead.
Eat & Drink
| Friday | Falorni for salami; dinner on the Greve piazza |
| Saturday | Lunch in Panzano — Dario Cecchini country |
| Sunday | Olio nuovo on toasted bread; last dinner in Greve |
| Monday | Espresso standing up at the Mercato Centrale, Florence |
Useful Links
- Consorzio Vino Chianti Classico — the official Gallo Nero consortium — producers, the appellation, visits
- Visit Chianti — regional tourist information, events and autumn programme
- Chianti cycle tourism — routes, gradients and bike hire across the Chianti hills
- Visit Tuscany — Chianti festivals — the regional food and wine festival calendar
Practical Notes
- E-bikes strongly advised. Greve has excellent hire — road, e-bike and trekking. With a motor the ridges are a joy; without one, two consecutive days here are a serious workout.
- Come for the oil. The last week of October is the olive pressing — olio nuovo is a genuine seasonal event and the single best reason to pick this week over any other.
- Priciest of the twelve once Tuscan hotel rates are counted, though still shoulder-season by Tuscan standards.
- Book Fontodi and Montevertine early; they are small and take limited visitors.
- Clocks change overnight on 24–25 October — welcome, given the climbing.