The venue
We've taken the villa.
Villa Grassina is a working wine and olive farm in the hills east of Florence, in an appellation called Chianti Rufina. It has its own cellar, its own olive press, a pool, a chapel, tennis courts and a restaurant. We've booked the main villa, the big house at the centre of it, for the two nights. The estate also has a farmhouse and some separate apartments, and other travellers will be staying in those.
We looked at ten places. This was the only one where all forty-three of us could sleep in the same building, with a pool and a playground and a wine cellar a few steps away, an hour from the airport, and nobody having to drive anywhere after dinner.
- Where
- Pelago, Florence
- From Florence airport
- 50 km, about 55 minutes
- Wine region
- Chianti Rufina
On site
Everything here is a two-minute walk from your bed
The party, the pool, the wine and your bed are all in the same place, so nobody has to get in a car. The pool, restaurant and grounds are shared with whoever is staying in the farmhouse and apartments, so we won't be the only people there.
Swimming pool and jacuzzi
Heated in October, which matters more than it sounds.
Their own Chianti Rufina
Grown, pressed and cellared on site. You can drink the view you're looking at.
An olive oil museum
A working frantoio with a museum attached. The olive harvest starts later in the autumn, after we've all gone home.
Cooking classes
Run on site. You make a full menu, then you sit down and eat it.
Restaurant and bar
Tuscan cooking from the farm's own ingredients, and a bar at reception for the evenings.
Tennis, football and basketball
Full courts. Someone is going to organise a tournament and it may as well be you.
Children's play area
Nine children are coming, so this wasn't a tiebreaker. It was a requirement.
A family chapel
Eleventh century, on the grounds. We're not getting married again, but it's lovely.
Bikes and hiking trails
Trails go straight out from the property into the hills. Bikes to rent at reception.
A farm shop
Honey, chestnuts, jams and the estate's own oil. Solves the souvenir problem without you leaving the property.
Parking, WiFi, fresh bread daily
Free parking for everyone, WiFi throughout, and bread delivered every morning.
A look around
The place itself
Photographs courtesy of Villa Grassina
Within an hour
What's around it
Three serious wine estates inside twenty minutes. Two castles, an abbey in the middle of a forest, and Florence itself under an hour away. Filter by whatever you're actually interested in.
Pelago
6 min· 1.7 km
The nearest village. A bar, a pharmacy and a shop, which covers most of what you forgot to pack.
Villa Travignoli
9 min· 4 km
A 550 year old Chianti Rufina estate that takes visitors. The closest serious wine to the villa.
Castello Nipozzano
15 min· 7.6 km
A Frescobaldi castle and cellar, so wine and a castle in one stop. Those were the top two answers on the guest survey.
Pontassieve
15 min· 8.5 km
A proper town. Supermarket, bank, pharmacy, and a station with direct trains into Florence.
Fattoria Selvapiana
19 min· 10.9 km
Another Chianti Rufina producer, and one of the best-regarded in the appellation.
Vallombrosa Abbey
23 min· 12.5 km
A Romanesque and Gothic abbey deep in the forest, founded in 1038. Frescoes, silence, very good air.
The Mall Luxury Outlet
23 min· 14.6 km
Gucci, Prada and the rest at outlet prices. Included without comment.
Vallombrosa forest reserve
26 min· 14.2 km
A national biogenetic reserve with marked trails. Best walking within half an hour of the villa.
Castello del Trebbio
27 min· 19.2 km
A 900 year old Medici castle with its own restaurant, cellars and a vineyard terrace.
Monte Secchieta
35 min· 23.1 km
A 10km trail with 500m of climb, and the views that come with it. For the ambitious only.
Fiesole
39 min· 24.5 km
A Roman theatre and Etruscan walls on a hill above Florence. Fewer people and a better view.
Florence, Ponte Vecchio
50 min· 31.3 km
The city itself. Fifty minutes by car, or take the train from Pontassieve and skip the parking.
Florence, the Duomo
55 min· 32.4 km
Brunelleschi's dome and the rest of the complex. Book the climb weeks ahead or you won't get in.
Drive times measured door to door from the estate in September 2026. October traffic is usually kinder than these assume.
Why the first weekend
We looked up thirty years of weather before picking the weekend.
Our anniversary is 22 October and for a while that was the plan. Then we checked. The 22nd sits in the wettest stretch of the month, with a 77% chance of rain across three days. The first weekend comes in at 60%, and it's the warmest of the month, a couple of degrees milder after dark, which is exactly when we plan to be outside.
So the party is three weeks early, on the grounds that we'd rather be outside for it.
80%
of October evenings here are completely dry
October looks wetter on paper than it feels. About a third of days in the month record some rain, but only a quarter of evenings do, because the rain here mostly falls overnight or in the afternoon. Across thirty years of records, four evenings in five stayed dry.
None of that is a forecast, obviously. It's thirty years of averages and October can still do whatever it wants. There's a roof over the restaurant if it comes to that.
Friday
21°C/ 13°C
70°F day · 55°F night
20%chance of evening rain
The warmest weekend in October, which matters most after dark.
Saturday
21°C/ 13°C
70°F day · 55°F night
22%chance of evening rain
Sunset is just before 7pm, so there's still light for a drink outside first.
Sunday
21°C/ 13°C
70°F day · 55°F night
24%chance of evening rain
Warm enough for a long lunch outdoors, cool enough to enjoy it.
What to pack
- A jacket for the eveningsDon't forgetDays sit around 21°C (70°F) and nights drop to about 13°C (55°F). That's a bigger swing than the daytime number suggests, and dinner is outside when the weather allows.
- Shoes you can walk on gravel inDon't forgetIt's a working farm. Gravel paths, a lawn, an olive grove. Stilettos will lose.
- Something waterproofDon't forgetA one in five chance of an evening shower isn't nothing, and when it does rain here it doesn't mess about.
- Swimming thingsThere's a heated pool and a jacuzzi, and early October afternoons are genuinely warm enough. People forget this and then regret it.
- A bag with room in itThere's a farm shop selling the estate's own oil, honey and chestnuts, and an outlet mall twenty minutes away. You won't be flying home lighter.
- Layers, not one big coatEarly October in Tuscany can feel like summer in the sun and properly cool in the shade on the same afternoon.
Figures from ERA5 reanalysis for the villa's coordinates, 1995 to 2024, via Open-Meteo. Evening odds use hourly data for 6pm to midnight, smoothed across a five day window.
Practicalities
Do I need a car?
Not for the weekend. We're arranging transfers from Florence airport and from the city, and everything on Friday and Saturday happens on the estate. If you're staying on in Tuscany afterwards, pick a car up on your way out, not when you land. You won't want one sitting in a car park for three days.
Pontassieve station is fifteen minutes away and runs direct into Florence Santa Maria Novella. That's the civilised way to spend a day in the city. No parking, and no restricted traffic zone fines.
