*POST UPDATED OCTOBER 2026
Friends, welcome to part four of my five-part Tuscan travel series! In this segment, I’m spilling the fagioli on one of Tuscany’s most overlooked gems: Castellina in Chianti. Just to recap quickly, earlier in this series I shared An Ode to Florence / 24 Hours in San Gimignano / A Quick Guide to Siena, and now this.
If you’ve never heard of Castellina in Chianti before, don’t worry – I hadn’t either. It’s a tiny little village up in the hills near Siena, with less than 3,000 inhabitants. Many tourists overlook Castellina in Chianti in favour of bigger towns with more attractions. The few that do stop here, often do so just for a couple hours en route to somewhere else. Frankly, it’s dumb, because as well as being wonderfully relaxing, the food and drink offering in Castellina is some of the finest in Tuscany.
Basically: it’s an adorable Italian village, nestled up in the rolling hills, filled with great food & fine wines, with little to no annoying tourists. Aka.. Tuscany’s best kept secret.
why castellina in chianti?
A sleepy hilltop commune, far removed from the hustle of nearby Florence – need I say more? We travelled to Castellina for one reason only: to relax. We basically always go to a city when we go exploring, and we wanted somewhere different this time. Somewhere we could recharge our batteries, drink great wine, & eat amazing food. The beauty of Castellina, for us, is that there isn’t really all that much to do there expect eat and chill out. The fact that it’s surrounded by breath-taking views was really just a plus for us.
getting there
These are the steps we took getting to Castellina in Chianti from Siena:
you have to make your way to the main train station in Siena – Ferrovia – which in itself is hard enough to get to. From Porta Camollia, you go down a series of escalators, which bring you into a shopping centre. Upon exiting the shopping centre, the train station is right in front of you. Duh. Nothing is that straightforward when it comes to Italy’s public transport.
there is a direct bus to Castellina in Chianti from Siena, but it only departs once every two hours, so you have to be ready! Unfortunately, you have to buy your ticket at Siena-Ferrovia, not on the bus, and there was only one ticket desk open when we were there. Despite getting to the station 30-minutes before our bus departed, we missed it and had to wait for two hours because of the extremely slow moving queue. Be sure to get to the station very early to avoid this frustrating aspect of Italian public transport.
once you’ve got your ticket, the bus to Castellina in Chianti departs just outside and to the left of the station. The journey takes roughly 35-ish minutes, but be sure to ask the driver to let you know when you’re there – it isn’t exactly clear otherwise.
the bus drops you at the main road passing by Castellina in Chianti, with the main section of town up to your right, and smaller guesthouses (like ours) and vineyards to the left. It’s a pretty small town, so don’t worry about getting lost.
Why didn’t we just drive!? We decided we didn’t want the added stress of renting a car and driving on the wrong side of the road (and there are a lot of sneaky driving fines in Italy that seem designed to catch tourists out, so be warned). Plus Italian drivers…
where to stay
