Cinghiale (Wild Boar) Ragu
Cinghiale is everywhere in Tuscan cooking, as the wild boar is a big part of the hunting culture here and of historic legacy to the region. The typical ragu is a red-sauce prepared with tomatoes and local herbs like rosemary and sage, but there's also an equally delicious wild boar ragu bianco made with white wine and a bit of cream. Either is a popular sauce with perfectly al dente tagliatelle or pappardelle, but you can't go wrong enjoying it with gnocchi either.
Where to Eat It
This is a ragu you'll most certainly find on the dinner table at local farms as well as being served up in family homes of the old villages dotting the countryside. Of course, walk into any trattoria in the region and you'll likely find this dish on the menu as well. Some specific restaurants in Florence to enjoy wild boar ragu include the humble but impeccable Osteria Brincello as well as the more upscale (and more well known) Cinghiale Bianco, which specializes in cinghiale but also does solid versions of other Tuscan staples.
Above all else, Tuscan cuisine is rustic. It's so earthy and humble, in fact, that Italians in the rest of the nation affectionately (so they tell us) refer to Tuscans as mangiafagioli, or "bean eaters." Tuscans did much to earn this reputation, as their fondness for beans dates back to 1528. For many years a humble but ubiquitous dish in the region was fagioli al fiasco (beans cooked in wine flasks). While that particular dish has fallen by the wayside, Tuscans do still enjoy comforting, hearty fare—especially ribollita, a bread soup made with vegetables and, yes, beans.
Where to Eat It
This is the definition of an "Italian classic" and no doubt every nonna in Tuscany has her own favorite recipe. A traditional ribollita is going to be cooked all day and served the next, using ingredients like day-old sourdough, local olive oil, local white wine, local sausages, and fresh vegetables like kale, carrots, onions, and celery.
If you're in Tuscany and jonesing for this cold-weather comfort-food, make a beeline for Florence and head to either Trattoria Sergio Gozzi, a historic restaurant which has been open over 100 years, or Vini e Vecchi Sapori, located in the city center, which is an intimate osteria that does solid versions of the classics.
Tuscan Cured Meats
As elsewhere in Italy, cold cuts are a staple of the Tuscan diet. You can find almost every kind of cured meat under the sun here, from hams to many varieties of salami. These rustic delicacies typically come from locally bred pigs raised in the wild or in semi-wild conditions. Sinta Senese pigs, from Siena, are a common breed that enjoy Protected Designation of Origin status (DOP) and are known for producing a distinct savory taste.
Where to Eat It
Three of the most famous cured meats in Tuscany are Prosciutto di Cinta Senese, Prosciutto Toscano, and Salame Toscano. The first is made exclusively from the Sinta Senese pigs mentioned above. You can recognize it by its bright red color and it's lower in fat content than the other two.
As for Prosciutto Toscano, this also has a DOP label and any true meats of this variety are prepared in factories only in Tuscany and dry salted with pepper and a mix of local herbs. Tuscan salami, on the other hand, is made from the shoulder, leg, and neck, and is mixed with back fat and red wine before being aged anywhere between 20 days to a year.
One other noteworthy (and fellow DOP designate) cured meat is Lardo di Colonnata, which is pork lard cured in local marble in the town of Colonnata.
For the perfect day out, head to any local delicatessen in Tuscany (you can't go wrong with the family-run La Norcineria, in central Florence) where you can pick up any or all of these cured meats. Throw in a bit of pecorino, a rustic sourdough loaf, and bottle of Chianti, and you'll have everything you need for a very tasty picnic.
Pappa al Pomodoro
In Italian, the word pappa literally translates to "baby food." But don't let that put you off. This is another typically rustic Tuscan dish that, like ribollita, utilizes day-old bread. It's an incredibly simple soup comprised of just bread, tomatoes, garlic, and basil. Of course, like most Italian dishes, the secret to a great Pappa al Pomodoro lies in the care with which it's cooked (as well as the addition of that divine Tuscan olive oil).
Where to Eat It
The best version you'll eat in this region will likely be served on a farm where you'll gather around a table with a welcoming Tuscan family. If that's not in your itinerary, then head to the intimate and humble Al Tranvai osteria in Florence, located in the Santo Spirito neighborhood south of the River Arno. For a spot that's more famous but has earned its reputation, there's Ristorante del Fagioli, which will not only make you a comforting Pappa al Pomodoro but you can eat it with an incredible steak, too.
Olive oil is a multi-tool of an ingredient: Tuscans use it in cooking, drizzle it over salads, and dip bread into it. There are so many extra-virgin olive oils produced different areas of Tuscany that local contests rank the best labels annually, and some regional varietals include Chianti Classico DOP, Toscano IGP, and Lucca DOP.
Where to Try It
The best way to sample as many as possible is to head to the Mercato Centrale (Central Market) in Florence and browse the vast selection. Here you can also pick up bottles of other goodies like vinegar and truffle oils.
Sangiovese grapes are popular throughout Italy, and a bit of a chameleon as they can take on many guises, from floral and fruity to dark and tannic. You can find the latter flavor profile in abundance in Tuscany's great Brunello wines, produced by Brunello di Montalcino in the vineyards surrounding the ancient town of Montalcino, located 50 miles (80 km) south of Florence. One of the more famous regional variations comes from Chianti, which comprises the area of hills and vineyards between Florence and Siena. Only red wines from the Sangiovese grape can claim the moniker Chianti.
Where to Taste It
There are plenty of other varietals of Tuscan wine, and you could spend many happy days indulging in tours of the most famous vineyards of the region. There's Antinori Chianti Classico, a globally popular brand whose winery in Bargino, just south of Florence, offers tastings of wines from throughout every region in Tuscany.
Avignonesi, located near the medieval hilltop town of Montepulciano dates to the 16th century, making it one of Italy's oldest vineyards. Here, there are many offerings including Vin Santo (a dessert wine made from white grapes), and Vino Nobile, another Sangiovese varietal once known as the "king of all wines." For an even older wine estate—Italy's oldest, in fact—visit the castle grounds of Barone Ricasoli, who trailblazed Chianti wine as we know it some 900 years ago.
If you're planning on sampling the fine cuisine of Tuscany, then you should also end the meal in true Tuscan fashion: with a cantucci or two. These twice-baked biscotti are a favorite after-meal treat, typically served with local Vin Santo.
Where to Eat It
Again, most trattorias in the region offer this staple combo (including the aforementioned Cinghiale Bianco, in Florence). You could also stop into any forno (pizzeria/bakery hybrid) in the region and pick some up to go. For a place that specializes only in cantucci, try Il Cantuccio di San Lorenzo, in Florence.