Castellina in Chianti | A Guide to Tuscany’s Most Overlooked Village


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.

castellina in chianti

castellina in chianti
castellina in chianti

why castellina in chianti?

A sleepy hilltop commune, far removed from the hustle of nearby Florence – need I say more? We traveled 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 breathtaking views was really just a plus for us.

castellina in chianti
castellina in chianti

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…

castellina in chianti
castellina in chianti

where to stay

Hotel Colle Etrusco Salivolpi  //  this hotel was everything we wanted and more. We visited Castellina in Chianti to relax, and this farmhouse-turned-guesthouse was the perfect oasis to unwind in after travelling around for so long. The house itself is beautiful, and our room was no different – exposed beams, wrought iron bed, antique furniture. The garden & pool area were wonderful, we loved being able to go out for a dip whenever it got too hot, etc. There was also a lovely little outdoor seating area where you could order a drink or just sit out to relax. It’s about a 10-minute stroll out of town, which was totally perfect for us. Address: Via Fiorentina, 89, 53011 Castellina in Chianti SI

castellina in chianti
castellina in chianti

where to get coffee

Bar Italia  //  a very casual place filled with locals only, all nattering away in Italian. Aka, the cafe of our Italian dreams. A great place for morning coffee & pastry, and wonderfully cheap! My favourite pastry was the vanilla croissant, which was stuffed to the brim with filling. Yum. Address: Via Trento e Trieste, 34, 53011 Castellina in Chianti SI

castellina in chianti
castellina in chianti

where to eat


Il Fondaccio  //  we were googling pizza places on the bus into town and this place popped up. A casual restaurant on the main thoroughfare – we weren’t exactly expecting much, but the pizza was surprisingly good! The base was excellent and the sauce to cheese ratio met our weird standards. Address: Via Ferruccio, 27, 53011 Castellina in Chianti SI

La Bottega del Borgo  //  such an adorable little wine bar! We stopped in for a meat/cheese platter one afternoon after looking enviously at other couples and loved the place! It was very generous for the cost and everything was delicious. I had a luscious glass of Vermintino with the platter, while Boyfriend enjoyed a glass of Chianti Classico. Address: Via Ferruccio, 76, 53011 Castellina in Chianti SI

Emporio Chianti  //  we stopped here for a glass of wine after lunch and ended up having practically a second lunch for the price of our drinks! A beautiful meat & cheese platter came with each glass of wine, with bread etc, it was so lovely! Address: Via Ferruccio, 7, 53011 Castellina in Chianti SI.
*2022 UPDATE: sadly, now closed.

Osteria Il Re Gallo  //  simple Tuscan food paired with great wines by the glass, at a very reasonable price. We shared a wonderful plate of differently aged Pecorino cheeses – one of which was so old it was purple! We didn’t exactly love the service here, but the value for money was unbeatable. Address: via toscana, 1, 53011 Castellina in Chianti SI

castellina in chianti


Ristorante Albergaccio di Castellina // one word: wow. We are genuinely surprised this restaurant doesn’t have a Michelin Star. Our entire experience was amazing, and the food was incredible. We ate so much goodness: a taster of a local tomato soup, a meat/cheese platter with fried sage, breads made in the traditional Tuscan style, pasta cooked risotto style with pesto & burrata creme, and ravioli stuffed with ragu & saffron mashed potato. The last two dishes were a particular highlight, and I haven’t even gotten to dessert yet. We ordered a dark chocolate mousse-like thing that was amazing, and we were given free lemon sorbet in homemade chocolate cones to cleanse the palate after. We were totally stuffed, but I wouldn’t change a thing. The wine was delicious, the staff were extremely knowledgeable, the setting was unbelievably romantic. A must-visit! Address: Via Fiorentina, 63, 53011 Castellina in Chianti SI

Restaurante Squarciulupi // all reviews for here say the same thing: make sure to sit on the terrace. Our table was right at the edge of the terrace, where we had an unobstructed view of the sun setting over the Tuscan hillside – it was truly magical. Of course, the food was also great. My favourite were the starters: fried dough balls, and deep-fried courgette filled with goats cheese; both of which were divine. We also enjoyed pasta courses of ragu with red wine sauce and duck ragu with olives, before sharing a beef fillet with black truffle & saffron mashed potato with fagioli for mains. All of which was as delicious as it sounds. Would recommend. Address: Via Ferruccio, 26, 53011 Castellina in Chianti SI

Le Tre Porte  //  here’s the thing: we thought the food here was very very good, but the service was terrible. We waited an age to get anything – menus, wine, food, the bill etc – but we genuinely enjoyed our meal, so I’m including it regardless. Both of us opted for pici pasta courses to start – Carbonara with Guanciale for me, Cacio e Pepe for Boyfriend – and we shared bacon wrapped pork with fried potatoes as a main. We ate every morsel, so it’s a real pity about the service. Address: Via Trento e Trieste, 4, 53011 Castellina in Chianti SI

castellina in chianti


Gelateria in Paese  //  possibly the best gelato we’ve ever had, anywhere. The pistachio was so salty and amazing, but we also loved the hazelnut, Nutella, and the salted caramel with peanuts. As you probably guessed, not a day went past that we didn’t stop by for gelato. Address: Via Ferruccio, 16, 53011 Castellina in Chianti SI
*2024 UPDATE: the website is showing this as temporarily closed? Hopefully it reopens soon!

castellina in chianti
castellina in chianti

what to see & do

Archaeology Museum  //  honestly, the museum itself is kind of small and disappointing, but it’s worth visiting to go up the tower for a view over the town. The fortress the museum is housed in was built by the Florentines to protect the territory from Siena way back when, so the views all around are beautiful. Address: Piazza del Comune, 17, 53011 Castellina in Chianti SI

Enoteca Bottega del Vino  //  a complementary tasting here was included with our hotel price, but anyone can arrange one. Admittedly, it was a little awkward at first, but fun once we got into it. We tried some wines – Chianti Classico and Super Tuscan – olive oils, balsamics, and vin santo. Address: Via della Rocca, 13, 53011 Castellina in Chianti SI

Via Delle Volte  //  an old covered passageway straddling the edge of town. It begins at the start of the town, across from the Church, and brings you out down the other end. There are houses & shops backing into the passage, and picturesque windows looking out over the Tuscan hills beyond.

Church of Saint Salvatore  //  the main church in town. Beautiful and peaceful, definitely worth checking out. Address: 53011 Castellina in Chianti SI

castellina in chianti

And there we have it, my travel guide to Castellina in Chianti. I hope you found it helpful and informative! If you have any thoughts I’d love to hear from you in the comments section below! My fifth & final segment all about Bologna will be coming to the blog in a few weeks, so sit tight.

Happy armchair travelling, friends!

Vicki xo

related posts:

An Ode to Florence
24 Hours in San Gimignano
A Quick Guide to Siena, Italy

1 thought on “Castellina in Chianti | A Guide to Tuscany’s Most Overlooked Village”

Leave a Reply

Your email address will not be published. Required fields are marked *