The weekend
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 on the list, 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. On e-bikes it becomes a genuine joy rather than a test. Late October adds the thing that makes the timing worth planning for: the olive harvest, and the first oil of the year pressed and poured over toasted bread while still cloudy and green.
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.
What it costs
Per person for the whole weekend, priced for a party of four — two twin rooms, or one whole place between you. Everything but the bed is fixed, so where you sleep is the only row that moves and the only one shown as a range.
| Per person | |
|---|---|
| Getting there, both ways | £152 |
| Three nights | £90–195 |
| Bikes and getting about | £79 |
| Eating, drinking and tastings | £185 |
| The weekend, per person | ~£510–610 |
Where to sleep
| Option | Per person |
|---|---|
| Hotels — two twin rooms | |
| Agriturismi outside Greve | €34 a night £90 for three |
| Hotels and villa rooms in and around Greve | €65 a night £170 for three |
| Airbnb and self-catering — one whole place | |
| The typical Greve listing — 518 of them, mostly whole houses | €75 a night £195 for three |
The dearest self-catering on the site by a wide margin. In Tuscany the villa is the product, and it is priced accordingly.
Eating and drinking
| What | Each |
|---|---|
| A trattoria dinner with house wine | €25–40 |
| A bistecca alla fiorentina, shared | €45–70 |
| A glass of Chianti Classico | €5–9 |
| Tastings in the Classico | €10–30 |
The £185 above assumes the middle of this list: a cheap lunch, an ordinary dinner, one good one over the weekend, and wine throughout. It does not change with the room.
Day by day
Friday 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 Up to Lamole, down to Panzano
- 24.6km with 511m of ascent — short, and the steepest ratio of climbing to distance anywhere on this site. Twenty metres up for every kilometre ridden.
- Lamole at 5km, and it starts almost at once: 236m at Greve to 587m at the top, terraced vineyards holding the slope at a gradient that has to be seen. The long view back down the valley is the reward, and it arrives before you have had time to regret anything.
- Then the ridge south, high and open, to Panzano at 15km on its spur above the Conca d'Oro — the golden bowl, a natural amphitheatre of vineyard that is the best single view of Chianti Classico there is.
- Lunch at Antica Macelleria Cecchini, arriving around half past twelve if you leave at nine. Dario Cecchini recites Dante over the meat counter and has done for decades. Book the sit-down; the counter is walk-in.
- Fontodi at 16km, in the floor of the Conca d'Oro. Organic since long before it was fashionable, and Flaccianello is among the finest reds in Tuscany. Book ahead.
- Then down, and up once more to Montefioralle at 23km — a fortified hamlet of one cobbled ring inside a wall, above Greve, with a kilometre and a half left to fall home.
24.6 km · 511 m of ascent · 228–586 m
Sunday West across the ridges, Verrazzano at the end
- 44.0km with 749m of ascent — well over the Saturday's distance and a third more climbing again. This is the hard day, not the Saturday, and nothing about it looks hard on a map.
- Down the valley through Greve at 3km, over Montefioralle at 4km, and up to the high point of 452m at 6km. That is the top — and then the day proceeds to cross ridge after ridge westwards, each one two or three hundred metres, which is where the 842m actually comes from.
- The Pesa valley at 24km is the far corner, and at 128m the lowest ground of the weekend. San Casciano itself sits a couple of kilometres further north and the route does not go in. Everything from here is uphill again in instalments.
- Castello di Verrazzano at 43km, with four kilometres left. Records from 1170: cellars, formal gardens and the old fattoria, and the navigator Giovanni da Verrazzano — who gave New York its bridge — was born here. Tours daily with a lunch option; book ahead.
- Greti at 44km, below the castle. In late autumn the frantoi around here are pressing, and the new oil — cloudy, green, and peppery enough to catch the back of your throat — is poured over toasted bread. It is a different substance from the stuff in supermarkets.
- Afternoon option, by car or taxi rather than bike: Antinori nel Chianti Classico at Bargino, a winery sunk into a hillside under a terracotta-ribbed roof planted with vines that you can walk across. Bookings all week.
44.0 km · 749 m of ascent · 128–450 m
The hard day is the Sunday
Every other weekend here front-loads the effort. This one does the opposite: 25km and 511m on the Saturday, 44km and 749m on the Sunday. If that is the wrong way round for you, the two swap without any other change — both days are loops from Greve.
Either way, 1,260m across two days on only 69km of riding makes this the steepest weekend on the list — eighteen metres of climbing for every kilometre ridden. Alba is close behind at 1,149m over 65km; Penedès climbs more in total, 1,440m, but takes 117km to do it. Nothing else concentrates climbing the way Chianti does, which is why the e-bike advice on this page is not hedging.
Monday 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.
When to go
Spring — March to May
10–21°C, the hills green, wisteria out, and irises in the verges. Showery but glorious, and the roads are empty. Radda and Panzano start their tasting calendars in May.
Summer — June to August
18–32°C. Hot on the ridges, and the climbs are unforgiving in the afternoon — even with a motor. The compensation is long light and swimming pools at every agriturismo.
Autumn — September and October
12–23°C, harvest in September, olive pressing in late October and November, and the hills turning. The best combination of weather and activity.
When to go
May or late September. Both avoid the July heat, which matters more here than almost anywhere else on the list given the gradients.
Festivals
None of this weekend assumes a festival. The rides work on any weekend of the season. If your dates land on the Expo del Chianti Classico on the second weekend of September, it fills the piazza in Greve, which is where both rides start and finish — ride in the morning and come back to it. The trade is worth stating plainly: on a festival weekend the growers are behind a stand in the square rather than showing visitors round a cellar, so book private tastings weeks ahead or accept that some will be shut, and expect beds to be scarcer, dearer and gone months in advance.
Spring
Radda nel Bicchiere — late May or early June
The growers of Radda pour together in the village square over a weekend.
Summer
Vino al Vino, Panzano — September
Panzano's own show, and the excuse to eat at Dario Cecchini's butcher's shop across the street.
Autumn
Expo del Chianti Classico, Greve — second weekend of September
The big one: the Chianti Classico producers filling Greve's piazza for four days.
Olive harvest and new oil — late October and November
The mills run and the new oil comes out green and peppery. Worth timing a trip around on its own.
Getting there
From London, per person, assuming bikes are hired locally rather than flown. Fares checked September 2026 and converted at €1 to 86p.
| Leg | Time | Cost |
|---|---|---|
| The flight | ||
| BA or Vueling, Gatwick to Florence (FLR). Ryanair and easyJet to Pisa are often cheaper but add an hour on the train | 2h 20 | £70 |
| Airport into Florence | ||
| Tram into the centre (€1.70) | 0h 25 | £2 |
| Out to Greve | ||
| SITA bus up into the Chianti (€5). A pre-booked taxi does it in 40 minutes | 1h 00 | £4 |
| Waiting and two changes | 1h 15 | — |
| Door to door, one way | 5h 00 | £76 |
| Both ways | £152 | |
Bike hire
Assumes e-bikes, or road bikes with low gears — Chianti is hills and nothing else.
| Shop | Rate |
|---|---|
| Officina Ramuzzi, Greve — hiring since 1995, and a workshop, which matters on these roads | €45 first day €40 second |
| BikeSquare, at the Greve tourist office — e-bikes, in the square itself | rates on request |
| Chianti Bicycles — gravel and mountain bikes for the white roads | rates on request |
The rate drops the longer you keep them: €35 a day from the third day on.
Getting about
| What | Cost |
|---|---|
| E-bike hire, Saturday and Sunday | £73 |
| SITA buses, allow | £6 |
| Getting about, whole weekend | £79 |
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.
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.
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 |
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.
Practical
- Italy allows cyclists 0.5 g/l of blood alcohol, the same limit as drivers. Ask for a spittoon; every serious cellar has one. See the country-by-country table.
- 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.
- The dearest of the Italian weekends 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.
- Check sunset before you plan the last leg. Any day that finishes with a ride home wants an hour of light in hand, and that hour disappears fast either side of the equinoxes.
- 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