A Wine Expert's Guide to Historic Chianti

Take a slow drive through the Tuscan countryside: It’s a stunning route with countless spots to pull over and capture iconic photos of the Tuscan landscape.

Gaiole in Chianti may have a small historic center, but it’s home to the Museo alle Origini del Chianti. It is a compact yet fascinating museum showcasing the origins of the Chianti region. With a collection of artifacts and stories, it offers a glimpse into the area's rich history. Just outside the town, you'll find Capannelle Winery, where you can taste classic Chianti Classico wines, including one of my favorites—50/50. This special blend is a collaboration with Avignonesi, another renowned vineyard just over the border in Umbria.

Radda in Chianti may be small, but it’s brimming with beautiful medieval architecture, making it well worth a leisurely stroll. While you're there, stop by La Bottega di Giovannino for lunch — you might even meet the original Giovannino or his son, who now runs the place. The food is fantastic, and the wine list is just as impressive, offering a perfect pairing for a relaxed, authentic Tuscan experience.

Castellina in Chianti is the most open and walkable of the three historic Chianti cities, making it a delightful place to explore on foot. A must-visit is La Rocca di Castellina, an ancient fortress perched atop the town, offering both a glimpse into the region's medieval past and panoramic views of the Chianti hills. You can tour the fortress and wander through its historical passages, while soaking in the beauty of the landscape. Castellina’s blend of history, accessibility and scenic beauty makes it an unforgettable stop in the Chianti region.

Montalcino: Brunello di Montalcino is one of the top red wines in the world, and it’s all crafted in the charming village of Montalcino. Like many smaller Italian villages, the best place to sample the town’s wines is at its enoteca, and in Montalcino, that’s the Fortezza. The Montalcino Fortezza offers not only a wide selection of wine flights but also exceptional food that pairs perfectly with their local wines. For a truly unique and off-the-beaten-path experience, book a luxury wine tasting at Casanova di Neri. Be sure to meet Giacomo, the winemaker, whose passion and expertise make the experience even more special. This tasting, complete with a gourmet lunch and some of the world’s finest wines, is a splurge, but it’s an unforgettable experience that will stay with you long after you’ve left. You can also stay at the property at their luxurious Relais.

Pienza: Just a short drive from Montalcino, Pienza is a charming 15th-century village that once served as the summer residence of Pope Pius II. The town is full of history and beautiful sites to explore, from its stunning piazzas to its Renaissance architecture. While you’re there, be sure to stop by Enoteca di Ghino. You can sample some of the region’s best wines alongside the knowledgeable proprietor, who’ll offer insights into the local terroir and winemaking traditions. It’s a perfect stop for wine lovers looking to dive deeper into the flavors of Tuscany.

Torre a Cone, while technically just outside the Chianti region, boasts a rich and intriguing history. During World War II, it was used to house priceless artwork stolen by the Nazis from Florence, and it was here that much of it was later recovered when the Nazis fled. The Rossi family — famous for Martini & Rossi — took over the estate and created the vineyard. Today, the winery offers a fascinating tour, delving into its storied past, and the wines produced here are truly world-class. Be sure to try their Merlot, which offers a unique expression far removed from the typical American style.

Tenuta Silvio Nardi is a hidden gem, offering a truly special tasting experience of both exquisite food and wine. This small-production vineyard, now run by Silvio’s daughter, is a testament to family tradition and craftsmanship. If you visit, be sure to ask for a tour of their barrel cellar (Barricaia). It was uncovered in the 1200s — an incredible piece of history that adds a unique depth to the experience. It's a perfect place to indulge in top-tier wines while immersing yourself in the legacy of this remarkable estate.

Ruffino is the name behind those iconic straw-wrapped Chianti bottles you might have spotted at your grandmother’s house, the ones that helped put Chianti on the map in the US. But that’s just a small part of the story. Ruffino has over 20 different labels, and only a select few make it to the US or even leave Italy. The winery itself is set in a stunning location, perfect for an outdoor wine tasting paired with a delicious lunch. It’s an experience that showcases the full depth and quality of Ruffino’s wines, far beyond the familiar basket-wrapped bottles.

Luiano Winery is a small vineyard near Strada in Chiani. Their tasting room is elevated up several stories to provide an expansive view of the vineyards. The staff is very helpful and does speak English.

La Bottega di Giovannino, Radda in Chianti: A small family-owned restaurant just inside one of the three League of Chianti cities. Wonderful food, a great wine list and friendly staff. This includes the son of the founder, who can provide a history lesson on the local wines and speaks excellent English.

Il Moro, Via Giuseppe Mazzini, 44, 53024 Montalcino: A small family-run restaurant in historic Montalcino. Make a reservation at one of their outdoor patio tables to enjoy epic views of the countryside from high above. The Mom and the Nonna cook the amazing food. The wine list is vast and one of the least expensive you will find in the area.

Osteria Il Postiglione, La Massa, P. P. Pasolini, 15, 50064 Figline e Incisa Valdarno. Just outside the Chianti region and minutes off the A1, this small restaurant specializes in the local Chianina Beef (the white cows that Parmigiana Reggiano cheese comes from). If you love beef, they serve it every way. It is typically prepared in the area, including Bistecca Fiorentina and my favorite, sliced beef marinated in Chianti. When they ask you how you like it cooked, say either “Sanguine”, which means rare or “Come il chef piace”, as the chef likes it.

Ristorante La Locanda dei Tintori Siena: One of the local specialties of Siena is Coniglio (Rabbit). Like me, you probably did not grow up eating rabbit. But, if you ever are going to try it, here. Order Coniglio all’Etrusca con Olive Taggiasche.

Baccus L'Osteria, Corso il Rossellino, 38/A, 53026 Pienza. Try the Pici Tartufo Nero Fresco. Pici is round long pasta, like a thicker spaghetti, that is “fatto in casa” or made in-house at this place. And, if it's summer, the Tartufo Nero (Black Truffles) will cover the entire plate.

Caffè Le Logge Ristorante Pizzeria, Piazza Giacomo Matteotti, 32, 50022 Greve in Chianti. A small, unassuming pizza place in a piazza in Greve in Chianti. The small city has a vibrant shopping district as well as great ancient architecture and many great restaurants. We like this little pizza place as a quick stop for good pizza.

Osteria Rosticceria Il Re Gallo, Via Toscana, 1, 53011 Castellina in Chianti. A small, charming restaurant in Castellina. Great personal service and the food was far beyond our expectations. A great place to try Cinghiale Ragu.