Chianti on the Hill

Perched on a hilltop in the Chianti countryside, this villa offers 360-degree views over the rolling hills that make it almost impossible to leave the terrace. The pool area is set up for long, unhurried days, with sun loungers, a pergola, and a poolside fridge – connected to the garden via an underground tunnel that keeps the whole outdoor setup feeling seamless. Inside, vaulted and beamed ceilings, terracotta floors, and restored fireplaces give the rooms a quiet grandeur. A separate ground-level cottage adds flexible accommodation and is fully wheelchair accessible. Fattoria Le Fonti winery and historic San Gimignano are just a short drive away.

Home truths:
* Due to this home's location, we recommend hiring a car to get the most out of your stay. There are eight parking spaces on site – four sheltered and four uncovered. The approach road to the villa is unpaved, so a vehicle with reasonable ground clearance will make arrival more comfortable, especially after wet weather.
* The pool is only open from the second Saturday in May until the last Saturday in September, so if you're visiting outside those dates you won't be able to use it. It's also 50 metres from the main villa, reached via a tunnel under the approach road.
* The beds in bedrooms two, six, eight, and ten can be converted into twin beds on request – worth letting your host know in advance if you'd prefer that configuration.
* While this home can accommodate two additional guests on a sofa bed in one of the living spaces, the maximum occupancy is 24 guests.