The Chianti Crawl: a round up of the best eats from an epic Tuscan road trip

Chianti. Land of the wild boar. Truffle. Bistecca. And of course… the Chianti Classico. With its seemingly endless backdrop of emerald green hills lined with grapevines and olive groves, it has got to be one of the best road trip destinations for foodies and oenophiles alike. And that’s exactly where my ex-flatmates and I descended upon this year for our annual bank holiday weekend tipple in search of the best wild boar pappardelle, truffle pasta and Bistecca the land had to offer.


Our pad for the weekend: the very quaint Fallochio house at Fattoria Corzano e Paterno a 140 hectare farm near the hamlet of San Casciano which produces it’s own wine, olive oil and Pecorino cheese. Just having breakfast overlooking their vast olive groves with herds of sheep running laps round us was an experience in itself.

Sadly, there were no truffles, boars or Chianina prime breed cattle on site, hence we were forced to leave paradise and go hunting outside of the farm’s grounds for sustenance. Fortunately though, my two comrades on the trip D and J had explored these parts before, hence we already had a shortlist of tried and tested restaurants we could rely on. Here’s the highlight reel from one epic Tuscan road trip.

1. La Bottega | | Piazza della Torre, 1, Volpaia, Radda in Chianti

The combination of traditional, home-cooked Tuscan fare and the amazing views from the top of this quaint yellow stone villa in Volpaia are unbeatable. Lunch alfresco here on a bright sunny day as we did and it will make for the most idyllic of experiences. There’s black truffle galore throughout their menu paired with freshly made pastas and rabbit even.

La Bottega, Volpaia (near Radda)

But it’s their rustic stews and ragus which really stole the show. Wild Boar was slow-braised to absolute perfection. The meat was tender enough to flake with a fork whilst the thick, deep red sauce was bursting with layers of flavour from the red wine, tomato, and bay leaf based reduction. Rabbit stew with black olives was equally as impressive. The ragu was somewhat similar to that used for the boar, but the addition of black olives and citrus gave the dish an added dimension. Don’t forget to order a side of their Fagioli beans as well. Served in a rich tomato sauce as opposed to just simply boiled, it’s so good I found myself lapping it up on its own.

Arguably my favourite restaurant in Chianti of the lot. It’s no surprise my buddy has earmarked this spot as his future wedding venue.

2. La Castellana | | Loc. Montefioralle 1, Greve in Chianti 

In the hills of Montefioralle above Greve, this cozy establishment’s bare stone walls, chequered tablecloths and hanging legs of ham oozes old school charm. You will find all your typical Tuscan favourites from fagioli beans to truffle pasta to a whopper of a Bistecca, chargrilled to absolute perfection.

La Castellana, Montefioralle (near Greve)

But it’s the wild boar pappardelle here that’s something else. The ragu simply melts in the mouth, releasing lashings of Chianti wine, rosemary, bay leaf and tomatoes with each bite. If you haven’t already filled up your alcohol quota by the end of the evening, there’s their arsenal of free flow grappas and dessert wines on the house you can help yourself to!

3. Al Macereto | | Strada del Canaglia 10/a, San Donato in Poggio

Sunday lunch at Al Macereto is a very family affair. There was a communion, a graduation celebration and an old couple’s anniversary all going on at the same time when we gatecrashed hoping to get a spot of lunch. Entire families from elder statesmen to toddlers in their Sunday best were sitting side by side on long banquet tables tucking into the huge portions coming out of Al Macerato’s kitchens. Kids, some barely 5 years old by my estimate were stuffing their faces with kilos of bloody Bistecca steak. It’s this early training that undoubtedly makes them foodies for life.

Al Macereto, San Donato

Despite the boisterous surroundings, we felt completely at home here thanks to a very warm welcome by our hostess and smiles from the local families around us. Sage fritters, compliments of the house and deep-fried in the crispest of batters was a real highlight. And although there was no shortage of interesting dishes on the menu, it’s all about the house speciality here: Suckling Pig (‘Maialino da latte’). Juicy and moist with a wonderfully crisp, aromatic skin, it’s an absolute must, especially with a pile of their lard-roasted ‘Greedy’ potatoes on the side. Some proper piggy goodness. 

4. La Fattoria | | Via del Cerro 11, Tavarnelle Val di Pesa

Another modest establishment that was bustling with both locals and visitors alike, La Fattoria’s menu reads like a greatest hits compilation of the Chianti region’s best dishes.

La Fattoria, Tavarnelle Val Di Pesa

Try the Ribollita – a thick, hearty bread and vegetable soup that tastes far better than it sounds, packing a real punch flavour-wise. And if you haven’t overdosed on steak by now, they do an outstanding Bistecca, cooked very simply over hot coals with plenty of sea salt and olive oil. In truth, the caramelisation on the meat could have been more even, but the sheer quality of the Chianina beef was what really won us over.  It’s easily the most tender, flavoursome piece of T-bone I’ve ever sunk my teeth into, rivaling even the most famous of establishments in Florence.  Choose from a wide selection of Chianti Classicos to wash down your steak, made by a whole host of local producers ranging from the upmarket Marchesi Antinori to the more modest, small batch Fattoria Corzano wine made on the very farm we stayed on.

Happy Days under the Tuscan sun.