Best Places to Visit in Tuscany

Join EuropeUpClose as we take a journey to some of the best places to visit in Tuscany. We will begin in Florence, then drive to San Gimignano with a stop at the fabulous Antinori nel Chianti Classico Winery. From San Gimignano we venture to the compelling town of Siena with its fantastic cathedral and famous horse races in the Palio. Another hour south and we’ll stop at Caparzo Winery near Montalcino before heading east to the beautiful hilltop walled city of Montepulciano.

Also read these articles on Tuscany:

Visit Florence

Florence is a natural starting point to begin your journey to the best places to visit in Tuscany. Known for the imposing red-roofed Duomo and Michelangelo’s David in the Accademia, Florence is a mecca for art, food, architecture, and history. You don’t want to miss the Uffizi Museum, the Central Market, and Ponte Vecchio, the bridge across the Arno River filled with shops displaying jewelry, crafts, and other fun products.

Also, read these articles on Florence:

Florentine Bisteca

And, of course, if you are in Florence, you must try the famous Florentine Bisteca. It is often referred to as some of the best steak in the world. We were lucky to have reservations at Trattoria dall’Oste Chianineria on Via dei Cerchi. Just a few minutes south of the Duomo, this iconic restaurant is well known for their Bisteca and other fine cuts of meat.

Florentines do like their steak rare, so be aware. You can order yours medium or medium rare, and it will most likely still come out very pink. One thing I liked about Trattoria dall’Oste Chianineria is that they brought out a hot plate along with the steak. That way, anyone who wanted their steak more done could cook it a bit more right at the table. Most of us ate it like it came, but there were a few in our party who preferred their steak more done. Sides included roasted potatoes, pasta with thinly sliced truffles, and some tasty bruschetta. For dessert, we completed our meal with a glass of Vin Santo served with tasty biscotti.

Wine Tasting and Lunch at Antinori Winery

With options of several great Antinori locations, we chose to tour the Antinori nel Chianti Classico vineyards just 20 minutes south of Florence. In a country where wine is a way of life, for twenty-six generations, the name Antinori has stood out.

We booked the special CRU Tour. This included a tour of the winery, a wine tasting of seven great wines, followed by a delicious lunch. This fully immersive experience featuring the wine-making philosophy of Marchesi Antinori following years of family tradition. Led by our outstanding sommelier, our tasting was held inside the fabulous wine cellar. Then we enjoyed lunch on the outdoor patio at the Rinuccio 1180 restaurant. This modernistic rooftop restaurant overlooks the gently rolling hills of the scenic Tuscan countryside.

Some of our favorite wines included a crisp Cervaro Della Sala Blend of Chardonnay and Grechetto and a Tignanello red blend of Sangiovese, Cabernet Sauvignon, and Cabernet Franc. The crowd favorite was the outstanding Brunello di Montalcino Pian Dellevigne Sangiovese. The following lunch on the beautiful outside terrance at Rinuccio made for a most pleasant day. This special vineyard among special vineyards in Tuscany is certainly worth a visit.

Explore the Hilltop Walled-Town of San Gimignano

After being totally wowed by Antinori nel Chianti Classico, we headed south to nearby San Gimignano. This was our third visit to this iconic Tuscan town – and we will be back again. No article about best places to visit in Tuscany would be complete without this idyllic town.

We stayed at the cozy Orto di Emma at Piazza delle erbe 4. The location is conveniently in the middle of this walled city. Restaurants, spectacular views, and attractions are just a few steps away. Without any train station in town, most visitors come via personal car or with a tour group. There is a bus that comes from the closest train station (~ five miles away), but check the schedules.

Eat at Fuoriluogo Ristorante

Fuoriluogo Ristorante is a wonderful family restaurant just a two-minute walk outside the walls. In addition to having wonderful food, the service, the artwork, and the friendliness of Mauro, Davide, Enrica, Christian, and the rest of the staff are all top-notch. It’s no wonder Fuoriluogo is one of the highest-rated restaurants in San Gimignano.

Mauro was gone for important meetings with Barolo. He continues to work on the fine wines the restaurant offers to diners. In his absence, the rest of the staff did a superb job of welcoming us and making us feel so special. Our outstanding waiter, Rafael, kindly suggested a recommended menu along with wine pairings, and we were so glad we agreed to take his advice. Julie and I enjoyed a fantastic meal with just the right wines paired with each dish.

Favorites included the Wild Boar Ravioli with citrus fruits in a saffron cream sauce, and a delectable Soft Organic Egg with sausage, red peppers, and gorgovino mousse. We also both loved the pizza, some of the best I’ve ever tasted. The light, tender crust had just the right flavors to complement the fresh tomatoes, cheeses, and fresh herbs. For dessert, we could not resist the tempting tiramisu.

In addition to the fantastic food and service, the artwork and ambiance of Fuoriluogo is superb. Davide is a wonderful artist and painted much of the beautiful artwork in the restaurant. The friendly staff, elegant but comfortable ambiance and outstanding food and drink make Fuoriluogo one of the top restaurants in San Gimignano.

Check Out Intriguing Siena

It was hard to leave San Gimignano, but we had Siena waiting for us. The charming walled city of Siena is famous for its beautiful cathedral and for the exciting Palio di Siena Horse Races held twice a year in the large central Piazza del Campo. We unfortunately just missed this exciting event. It normally takes place twice a year on July 2 and August 16 every year. Preliminary events take place the three days before the official race. Since this is a very popular event, plan early if you want to attend during the races.

Following lunch on the lovely outdoor terrace at ViVace Ristorante and Wine Bar, we walked the short 10 minutes to the beautiful gothic Siena Cathedral. This impressive structure was built between 1215 and 1267 and features artwork from artists like Michelangelo, Donatello, and Pisano. With its iconic greenish-black and white stripes, this historic icon is striking inside and out. Other great attractions in and around the cathedral include the Piccolomini Library, the Museo dell ‘Opera, Baptistery, Crypt, Oratory of San Bernardino, and Diocesan Museum of Sacred Art.

Drink Brunello Wines at Caparzo Winery in Montalcino

With so many outstanding wineries around Montalcino, we picked Caparzo Winery to have a tasting and to explore. My new daughter-in-law became acquainted with Caparzo while watching the fun Letters to Juliet movie from 2010. There are some scenes in the movie from one of the many Caparzo winery locations in Tuscany. We thoroughly enjoyed our tour and tasting at Caparzo Winery, especially their world-famous Brunello di Montalcino. An added bonus was the spectacular scenery on our road trip from Montepulciano to Caparzo. Located in the picturesque hills of Montalcino, with fields of red poppies next to golden fields of wheat blowing in the breeze.

Eat and Drink your Way through Montepulciano

So, after visiting the walled cities of San Gimignano and Siena, we had another walled hilltop city on our itinerary: Montepulciano. Our return to this fantastic village was equally full of great food, wines, views, history, and special people of the town. This very walkable small town is anchored by the Grand Piazza, and is famous for its Vino Nobile red wines. Another notable landmark includes the Torre di Pulcinella. This clock tower is topped by the whimsical figure of the Pulcinella, a classical comedic character.

We also found the “underground city” of this hill town fascinating. Miles of tunnels, rooms, and cellars have been carved into the rock underneath Montepulciano, making for a fun and educational tour. We went to the popular Cantina Ercolani for a tour and wine tasting. Other popular wineries in Montepulciano include Cantucci Winery and Cantina de‘Ricci.

Eat at L’Altro Cantuccio Ristorante

L’Altro Cantuccio Ristorante is a fabulous family-run restaurant just a few minutes’ walk from where we stayed at the lovely Montepulciano Bed & Breakfast at Via Di Gracciano. Chef Mattia Putzulu and his lovely wife, Monica, a Sommelier, have created one of the best dining experiences in Montepulciano. L’Altro Cantuccio exudes old-world charm. Modern appointments along with the historic stone, wood, and brick is the perfect blend of old and new.

Mattia and Monica graciously hosted us for an extremely memorable evening. For starters, we enjoyed an outstanding Tuscan and Cinta Senese salami, Pecorino cheese of Pienza, and a selection of homemade fruit mostarda. Our server also brought a stuffed golden tomato held by a sculpted hand along with an excellent 100% Sangiovese wine.

For my main course, I had the Cheek of Chianani Beef cooked for 50 hours, with spicy vegetables, citrus fruits, and dill. The beef cheek was extremely tender and flavorful. It was one of my favorite dishes during our three-week visit to Europe. My wife had the equally excellent grilled Chianani flank steak. Other enticing mains on the menu included the Lamb with ember, coconut, mint, and radish, and a crispy salt cod with artichokes and burrata cheese.

Dessert was the amazing Underworld, an artistic and decadent concoction of chocolate mushrooms, acorns, and undergrowth – a true masterpiece! Each bite brought out the intense flavors of chocolate, cream, and nuts. I would loved to have brought one back to the states to share with family and friends, but I don’t think it would travel well (plus, I would probably eat it all before our return!).

L’Altro Cantuccio has deservedly earned its reputation as one of the top restaurants in Montepulciano. Do yourself a favor, and let Mattia and Monica treat you to a fantastic dining experience in their lovely hilltop restaurant.

Discover Top Places in Tuscany For Yourself

Obviously, there are so many great places to visit in Tuscany that no one article can capture them all. Many are relatively unknown and just waiting for you to discover them. We hope by introducing you to just a few of the many options you will be inspired to come visit for yourself. Tuscany is indeed one of Italy’s treasures and should not be missed on any Italy itinerary.

Best Places to visit in Tuscany was written and photographed by Scott Kendall for EuropeUpClose. Thanks to our gracious hosts, including Fuoriluogo Ristorante and L’Altro Cantuccio. All opinions are those of the author.