A Week Exploring Tuscany

You can’t talk about Tuscany without mentioning the rolling green hills, the Cyprus-lined roads, the garnet wine, and the flavors of cheese, truffle, and pistachio dancing on the tongue. The sunsets seem to glow brighter here, and as I took in the beauty of the landscape after a day of wine tasting or exploring medieval towns, I began to fall deeper into Tuscany’s delightful spell.

For the final part of our two-week trip to Italy in early October, we spent 6 nights at an antique villa near Florence in the commune of Montespertoli. The villa we stayed in was among the best rentals I’ve ever stayed in. Boasting an age of about 800 years, the home featured a stone façade, antique décor, rustic details, an outdoor dining pavilion, and views of the lush landscape. We enjoyed reveling in the atmosphere of the villa, so we spent plenty of time relaxing on the property. Some of my fondest memories were resting on lounge chairs and feeling the coolness of the autumn breeze or having breakfast under the energizing glow of the morning sun.

However, relaxation was not the only activity on our itinerary. We spent most of our days in Tuscany exploring various villages, cities, and vineyards. This was my second visit to the region, but I felt just as warm and dazzled by the history, flavors, and beauty that Tuscany has to offer. I have listed all of them below.

San Gimignano

This medieval town is also called “The Town of Fine Towers,” and its skyline is dominated by them. While simplistic in design, the brute towers add unquestionable valor to the aesthetic that doesn’t let one forget its fortified history. Once inside the town’s walls, we found the streets lined with stone, dust-colored buildings made lively by modern shops with souvenirs, treats, leather, jewelry, and clothing. The shopping was more impressive than I expected and we spent a lot of time browsing shops along the main road. We stopped for lunch at a streetside restaurant with a fantastic spaghetti bolognese. Later, we had gelato at Gelateria Dondoli, famed for winning several gelato championships. I tried the pistachio flavor and quickly understood why it has won awards. Being as smooth as silk and just sweet enough, it was the best gelato I have ever put in my mouth.

Before we left, we went into the Sacred Museum of art and climbed the Torre Grossa. Even though the museum was small, the religious artwork was profound, and the views of the hills of Tuscany from the tower were awe-inspiring.

Wine Tasting at Castello il Palagio
Chianti and Tuscany are synonymous, so I was excited to do a wine class and tasting at a picturesque 13th-century-castle-turned-vineyard. In the class, we learned how the different wines of the region are produced. The most fascinating to me was learning the difference between Chianti and Chianti Classico. Chianti is more of a broad term for regional wine and allows a more extensive mix of grapes, while Chianti Classico has a stricter standard and can only be made in a tiny part of Tuscany. We were in one of the very few communes that produce Chianti Classico. After the class, we got to tour the vineyard and taste the grapes fresh off the vine. We then proceeded to taste many types of wine alongside a homemade lunch that included 6 courses. Having lunch in a Tuscan vineyard while laughing with people from other parts of the world was an enriching experience.

Being the birthplace of the Renaissance movement, Florence is an art enthusiast’s dream. Our first stop was at the Uffizi Gallery, where we saw incredible works from artists like Botticelli, Caravaggio, Leonardo da Vinci, and Michelangelo. While there were many marvelous pieces in the gallery, I was most excited to see the “Birth of Venus” and “Primavera” by Botticelli. I love the use of color and form in these pieces.

After that, we were ready for some paninis, which Florence is famed for. We found a small spot off the Piazza della Signoria called La Nicchietta in Callmaruzza. The shop is a small counter with an array of meats and cheeses with a cheerful man behind it. I chose a sandwich with salami, ricotta, and dried peppers, which was absolutely divine.

We spent the rest of the afternoon shopping for gold on the Ponte Vecchio and leather in the San Lorenzo Market. While these places are designed for tourists and perhaps a bit overpriced, I enjoyed the experience and bought some quality items. For dinner, we had gnocchi at Osteria Santo Spirito. I don’t think I’ve ever had more tender and fresh gnocchi. I recommend the truffle gnocchi for cheese lovers and the gnocchi in ragu sauce for people wanting more savory fare.


Made famous by the movie Under the Tuscan Sun, this idyllic hilltop town holds all of the charm and quaintness you’d expect from a Tuscan village. Rustic streets, intimate plazas, quaint cafes, and an overall sense of community make Cortona a must-see for anyone visiting Tuscany. We stopped here for the afternoon on our drive back to Rome and thoroughly enjoyed our visit. We winded through the charming streets and popped into a few shops where I bought some artwork. We had lunch at La Grotta. The food was incredible, and the outdoor seating was in an intimate courtyard surrounded by stone homes. While Barga held the number one spot for my favorite Tuscan village, Cortona may be tied with that place.

Overall, I will never get enough of Tuscany. Italy is a beautiful country with exciting cities and beauty on every corner, but Tuscany offers a sense of tranquility that I haven’t found anywhere else. The atmosphere here encourages one to become reflective and at ease. I am beyond grateful that I have spent so much time there this year, and I hope to return one day.

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