A group trip to Chianti, Italy

A villa for the group, vineyards out of every window, and nothing to do but lunch. Best months for a group: May, June and September. Our estimate for three nights in May is about £363 each from London, flights plus a share of the bed.
When to go
Chianti is in season for a group in May, June and September, the months we would pick first. Average daytime highs are 22°C in May, 28°C in June and 26°C in September. Outside those months it can still work, it is simply what our catalogue rates highest for a trip with friends.
What it costs from five cities
Our estimate for one person in a group of four sharing one place for three nights in May, in pounds. Every figure here is an estimate from the same pricing annamo uses on the shortlist. Before anyone books, annamo checks real fares for your own dates from every home city.
| From | Total | Flight, return | Bed |
|---|---|---|---|
| London | About £363 each | Flight £113, usually £85 to £145 Our estimate, from real prices in other months | Bed and a share of a hire car £250 |
| Paris | About £402 each | Flight £152, usually £115 to £205 Our estimate, from real prices in other months | Bed and a share of a hire car £250 |
| Barcelona | About £354 each | Flight £104, usually £80 to £135 Our estimate, from real prices in other months | Bed and a share of a hire car £250 |
| Milan | About £374 each | Flight £124, usually £85 to £180 Our estimate, from real prices in other months | Bed and a share of a hire car £250 |
| Amsterdam | About £498 each | Flight £248, usually £170 to £360 Our estimate, from real prices in other months | Bed and a share of a hire car £250 |
Our estimate Flights from our flight model, fitted on 6,159 real fares up to 4 October 2026, and where a row says so, real prices on that route in other months, moved to May for the season, from fares seen in the 120 days up to 8 October 2026. The usual range is where two real fares in three land: 70 to 145 per cent of the model figure, or the spread of real fares on the route where we have them. Beds from our bed model for the price level of the place. Not a quote.
What Chianti is good for
- Food: excellent (5 out of 5)
- Nature: very good (4 out of 5)
- Culture: good (3 out of 5)
- Wellness and spas: good (3 out of 5)
Things people go for:
- Wine estates
- Greve in Chianti
- Hill town drives
Who it suits
- Active groups who want walks, hikes or time on the water
Getting there
The airport is FLR. An hour south of Florence airport. A car is needed.
FAQ
How much does a group trip to Chianti cost?
Our estimate is about £363 each from London for three nights in May, flights plus a share of one place for a group of four. It is an estimate, not a quote, so check real prices before anyone books.
When is the best time to go to Chianti with friends?
May, June and September suit a group best by our reckoning, with average daytime highs of 22°C in May, 28°C in June and 26°C in September.
How do you get from the airport to Chianti?
An hour south of Florence airport. A car is needed.