What do James Bond, medieval towers, and grapes have in common? Almost nothing. However, I recently discovered that all of them have a common link with the beautiful Italian region of Tuscany.

If there’s one stop I wanted to make on our two-week, whirlwind tour through Italy, it was Tuscany. It may surprise you that my vision of Italy never included the Leaning of Tower of Pisa, piles of homemade spaghetti, or even the iconic Colosseum. Blame my hopeless addiction to cheesy rom-coms, but when I envisioned Italy, I saw the rolling hills of Tuscany or feasting on rustic farm bread and wine, all while soaking up the Tuscan sun with a handsome stranger. 

Substitute the stranger for my equally gorgeous husband and you have one of the best days of our trip. With only one day to spare, we knew that to make the most of our time in Tuscany we would need a knowledgeable guide and a mode of transportation. Enter our friends at Walks of Italy. Thanks to them, we were able to fit in all the romance, history, and food for which Tuscany is famous.

Our day started with an early pickup in a wonderfully air-conditioned van (complete with Wi-Fi, a blogger’s dream). Giulia, our guide for the day, introduced herself and laid out our itinerary. We had an entire day to explore Tuscany, but first, we had to make a stop to bid a quick farewell to our departure city of Florence. Piazzale Michelangelo in the city’s Oltrarno district is the place to go for a stunning photo op of Firenze (as the locals call it).

Taking in Florence with our Walks of Italy guide

A winding road lined with cypress trees led us to our first stop in the medieval town of Siena. The town is known for its Romanesque architecture and revered Palio run. The latter is a cherished tradition of horse racing that happens twice a year. This event was even featured in the opening scenes of the James Bond film Quantum of Solace. To outsiders, it may look like a spirited testament of a horse’s ability, but the bloodlines of this event run deeper.

We learned that Siena is divided into 17 different neighborhoods or contrade. Each one is equipped with its own colors, mascot, and coat of arms. The Palio is essentially a face-off between horses from each of the rivaling Siena contrade. The winner of the event takes home the coveted title of victor until the next year. Our guide Giulia had proudly married into the “goose” contrada and scoffed when I pointed out that I liked the white, black, and orange coat of arms from the “she-wolf” district.

Viewfinder Tip: Look down while inside the Siena cathedral—the intricate mosaic floors might be the most stunning part of the interior.

After we hoofed around the piazza where the Palio takes place, we headed toward the Siena duomo. This medieval cathedral might be a stunner on the outside, but the true beauty lies within. The gorgeous frescoes, marbled columns, and detailed sculptures could have entertained me for hours, but the true treasure of the cathedral is its Piccolomini Library. The giant manuscripts looked like they belonged in a fairytale, and art aficionados would be enchanted by the detailed and preserved frescoes.

Siena could have taken up the entirety of our day, but we knew there was more to see. We saddled up, back in the van, and headed toward the walled medieval town of San Gimignano, a UNESCO World Heritage site. We only had an hour to take in the town, but it was just enough time to grab a much-needed espresso and explore the two things the town is known for: its towers and its gelato.

The city’s famous commanding towers were originally erected as a sign of status and wealth. Once, over 70 towers dotted the landscape. Today, the 13 towers that remain have been transformed into apartments or shops.

One of San Gimignano’s remaining 13 towers

There was one shop in the middle of the town square that caught my eye. The long line and towering cones of gelato were a tip-off that we were in the midst of greatness—the acclaimed Gelateria Dondoli. A quick scan of the gelateria’s unique flavors left no doubt of its claim to multiple titles from the Ice Cream World Championship (yes, that’s real). Mouthwatering flavor combinations like the Champelmo (pink grapefruit and sparkling wine) and Rosemary Baby® (raspberry and rosemary) had me drooling. There was even one that was gorgonzola-and-walnut flavored. Since lunch was coming up, I attempted to be responsible and foolishly turned down a scoop of this famous gelato. It might be a mistake that I regret for the rest of my life (or at least until my return visit to Tuscany).

All of that exploration worked up quite the appetite and I welcomed our next stop at the Tenuta Casanova farm. Rita and Silvano’s beautiful home and organic farm is nestled on a hillside just minutes from San Gimignano. The couple graciously gave us a tour of their vineyards and introduced us to their “pets” including bees and wild boars.

It wasn’t long before we were ushered to the cellars to see how grapes were fermented and transformed into precious wines and balsamic vinegars. Silvano let us taste our way through the fermentation process as he poured multiple glasses of the incredible Chianti for which the region is known, and wooed us over several samplings of aged balsamic (one was even older than me). Give me a loaf of bread and free reign over the balsamic vinegar and I could have stayed in the cellar all afternoon. It was only the promise of lunch (and more aged vinegar) that lured me from the tasting room.

Toasting our wonderful meal at Tenuta Casanova

Our first course was a personal platter of local cheese, warm homemade bread, and honey. We were also served heaping portions of rustic beans and a beautiful and refreshing caprese salad. Truth be told, I was already a little full after the first course, but we enjoyed a second course of Parma ham with a side of truffle-laden scrambled eggs. The pièce de résistance was incredible lasagna. It was nothing like the Stouffer’s frozen stuff that we’re used to in the United States, but instead consisted of handmade pasta, fresh organic tomatoes, and the creamiest of béchamel sauces. Each course was obviously paired with a glass of wine. 

Dessert was smooth vanilla gelato served with our choice of aged balsamic vinegar. I wouldn’t have thought to top my ice cream with vinegar, but aged 30 years, the balsamic was more like delicate syrup. I could not get enough.

While it would have been ideal to spend an entire week eating and exploring our way through Tuscany, both my liver and my already-too-tight clothes were grateful that we fit in as much as we did in one day. That being said, I look forward to our return and a taste of that famous San Gimignano gelato.  

If you only had one day in a city, which city would you choose?