Who doesn’t want to stay in a villa in Tuscany? It’s basically the dream, right? I set aside three days for my own Tuscan adventure and found the secluded Studio Fonte Lattaia, surrounded by vineyards in the Val d’Orcia. I should note that the wine region includes multiple villages surrounding Montalcino, but to simplify I’m bucketing everything under the main town that is also the namesake of the famous Brunello di Montalcino wine. Got it? Good.

While the Chianti Classico region is an easy day trip from Florence, Montalcino is about a two hour drive (give or take) from both Florence and Rome, making it a less-touristed destination. On my last trip to Florence, I had partook on a Chianti wine tour with my friends Jen and Ross, whose stay in town serendipitously coincided with mine. This time around, I was looking forward to exploring another Tuscan wine region slightly off the beaten path.

Getting to Montalcino

My itinerary called for me to take the train from La Spezia back to Florence, where I’d rent a car. From there, I’d embark on my first-ever experience driving in a foreign country, arriving in Montalcino 5-6 hours after departing La Spezia, if all went as planned.

I first had to take a train to Pisa, then transfer to a train bound for Firenze SMN.

Then the train from Pisa to Florence was delayed. Fortunately, the trains ran frequently on that route, so it was just a 20 minute hiccup. Once arriving back in Florence, I navigated to the Europcar office (10 minute walk) with all my luggage, and arrived a sweaty mess. The check-in process was surprisingly easy – they didn’t try to upsell me on anything, and they assured me it would be fine to drop off the car in central Rome as I had originally planned, although I wouldn’t be charged extra if I opted to return the car at FCO.

Next I headed to the garage a couple blocks away (more perspiration ensued) and found my Mercedes E-class. One of the most anxiety-inducing parts of my Italy trip was the prospect of driving. I had never driven in a foreign country and I had heard horror stories about the aggressive drivers. Having lived in Manhattan for almost five years, my driving skills were a little dusty, so I figured booking a luxury sedan would at least give me an extra oomph as I navigated the streets of Italy on my own.

Getting out of the narrow yet busy streets of Florence was the scariest part. I had never realized how many Vespas were on the roads in town until I had to make a concerted effort to not hit them with my comparatively gargantuan vehicle.

Once I made it on on the highway, it was smooth sailing. Yes, the cars drove fast. They didn’t seem to understand and/or appreciate the value of using turn signals when switching lanes. I quickly realized that “controllo della velocita” signs meant that speeds were automatically tracked, but the Autovelox machines used were clearly marked (people would literally slam on their brakes to slow from 160 km/hr to 110 km/hr and then speed right back up again). Before long, I was driving like an Italian and loving it.

After approximately an hour gliding down the Italian highway, I reached Siena, fumbled around for a bit until I found a parking garage near the old town, and was on my way for an impromptu self-guided walking tour.

My time in Siena was short-lived, as I had an appointment to meet Emanuel, the cellar master at Terralsole (Bruno, the owner of Terralsole, also owned my studio, but was out of town with his family). Emanuel would give me a winery tour, tasting and escort to the studio, as it was apparently so secluded it would be difficult to find on my own.

Emanuel was a hoot. He apologized for his poor English (1000% better than my Italian, at least) and proceeded to taste the Terralsole wines alongside me. Born and raised in Tuscany, wine was in his blood, and he was bringing up his children in the same vein. He told me stories about his six year old daughter describing the notes in different wines. Sounded like her palate was already more refined than mine was.

As much as I was loving Emanuel’s hospitality, I eventually begged him off, as I needed to get to Studio Fonte Lattaia, find a supermarket and get back to the studio without killing anyone in the process. Emanuel assured me that drinking and driving was not a big deal, but I insisted that we end our already indulgent tasting party and get on our way.

The closest supermarket was about 15 minutes away and I may have made a few wrong turns, but I arrived with plenty of time before the store closed at 7pm. En route, I had a blast making my way through the streets surrounded by vineyards and medieval villages. Even though it was a windy and dusty afternoon, Montalcino was already exceeding my expectations.

My Tuscan Studio-Villa

Honestly, I’m not sure what designates a villa from any other old property. Calling my one bedroom vacation destination a “villa” seems overblown, but “studio” seems underwhelming. I’ll share my pictures and you can decide for yourself.

Montalcino Wine Tour

Guess what I planned for my first full day in Montalcino? Wine tour, surprise, surprise. I couldn’t find a small group tour in the region, so I decided to splurge on a private tour through Montalcino Wine Tours. It was my first time doing a wine tour on my own, and while it was a bit awkward at times, the personal attention made the experience incredibly special, and changed my view on wine tours, travel (and life, to a certain degree) in the future.

The tour was already off to a great start when I emailed my guide Giovanni (Gio for short) with my pick-up location. “I love Bruno’s place!” he responded. I was still in Spain at the time, but happy to hear that my choice of Montalcino accommodations garnered Gio’s approval.

Gio picked me up at 9am in a Mercedes mini van. Thin but fit, he had a tousled mop of curly dark hair and appeared to be slightly older than I was. Not bad-looking at all. This was going to be fun.

The plan was to stop at three different wineries of varying sizes. Before the last winery, we’d stop at Gio’s restaurant for lunch (in addition to wine tours, he offers cooking classes, hiking tours, truffle hunting outings and more).

The first stop was Argiano, the largest of the three wineries we’d visit. After touring the sprawling vineyards and production facilities, we settled down for a tasting of Brunello di Montalcino, Rosso di Montalcino (both made with Sangiovese grapes) and Solengo, Argiano’s Supertuscan blend of Cabernet Sauvignon, Merlot, Petit Verdot and Sangiovese.

As I noted earlier, it was a little awkward tasting on my own since Gio and the Argiano guide would look at me intently after each sip to gauge my reaction. I felt self-conscious at first, as if I needed to come up with an expert analysis of each wine’s tasting notes. Fortunately, Gio tasted some of the wines with me (he would spit, unlike Emanuel from the previous day), relieving some of the pressure. Gio was knowledgeable and opinionated, and I preferred to learn from him rather than invent my own inexpert statements. I left with a few bottles to take home and we were on our way.

The next stop was SanCarlo, a smaller, family-owned winery. We were met there by Gemma, whose father and grandfather had run the business before her.

Gio and Gemma were friendly with each other, and talked a bit about the local wine industry politics as we toured the property. I got the sense that it was a tight-knit community, and that people generally all knew each other.

As I mentioned earlier, Brunello and Rosso are both 100% Sangiovese, although Brunello is considered to be of superior quality and commands a higher price. Brunello is one of the four original DOCG wines, which is the highest classification in Italy (fun fact: the other three original DOCG wines are Barolo, Vino Nobile de Montepulciano and Barbaresco). As such, for a wine to qualify as Brunello, it must meet strict requirements such as aging minimums and yield restrictions.

Rosso di Montalcino is a DOC classification, which still requires the grapes to be 100% Sangiovese and sourced from the viticultural region, but offers much more relaxed rules on aging. As a result, Rossos can be released much earlier than their Brunello counterparts.

Enough of the wine lesson. After the second tasting, we headed to Gio’s property, where he had a restaurant, farm and facility for cooking classes.

Originally from northern Italy, Gio had moved to Montalcino years ago to work in the wine industry. Starting in PR and journalism, he eventually decided to strike out on his own, bought the property and put in the hard work to clean it up himself. He convinced his younger brother and sister to join him in Tuscany, and they now ran a family business (his brother served lunch while Gio and I ate and chatted).

Gio let me know that he didn’t usually eat with his guests, only the ones he liked. I think he also felt bad that I was by myself and didn’t want me to feel lonely, but I accepted the compliment. He told me about the ideas he had to continue to grow the business, but admitted that he was busy and needed help. At one point, he jokingly suggested that I move to Tuscany to help him with sales and marketing (at least I took it as a joke, although the idea was tempting). He mentioned that he also did hiking tours in the Dolomites (the Italian Alps), where he had grown up. Immediately, I started thinking about how I could fit in a September trip (Gio said September was the best month for hiking) to the Dolomites – 2019 was booked, but maybe in 2020?

After lunch, we had one more winery to visit: another small, family-run production whose name I now can’t recall.

The wine at the last winery was my least favorite, but I enjoyed the homey, charming ambiance. The day had began overcast, but the clouds were finally starting to part, and the brilliant sunshine lit up the rolling, verdant hills. Gio had been attempting to teach me Italian all day, so I tried to practice with the adorable nonna (Italian grandmother) at the winery. “Piacere di conoscerti,” I told her as she beamed at me. “Brava!” Gio applauded me.

Then it was time to head back to my studio. “You have this whole place to yourself,” Gio commented. “What are you going to do tomorrow? Do you know anybody in the area?” Was he trying to hint at something?

“No, I don’t know anybody. I’m just going to go for a run, relax by the pool, read, cook. It’s not like I’m going to go to a bar by myself,” I told him.

“No! You going to a bar by yourself here… that would be dangerous,” he responded. “Well, not like dangerous dangerous, but you know…” he trailed off with a blush. Yes, I did know what Italian men could be like, Gio.

Also a runner (a much better one, I figured), Gio recommended a path nearby. As he dropped me off, he gave me his card. “Call me if you get lonely tomorrow!” he said. It was his day off; I guess he was hinting at something, but I was too shy to take him up on it. Besides, I really was looking forward to a peaceful day on my own.

Relaxing Final 1.5 Days in Tuscany

My stay in Tuscany had been even more magical than I expected. Running through vineyards, lounging by the pool, cooking fresh meals, drinking local wine… I could easily have stayed for weeks. Gio’s comment about moving to Italy was sounding more compelling with every passing minute.

I had also been so impressed with everyone that I met. All of them lived and breathed wine, and most of them led relatively simple lives – working in the farm or the vineyards, striving to produce great wine, maintaining a business so they could lead a happy life, not so they could make gobs of money. Perhaps I was being idealistic, but the idea of a slower-paced life didn’t seem as dull or boring as it once had. Perhaps it could even be satisfying and fulfilling?

I still had many months to mull things over. Next up, three final days alone in Rome, then I’d meet up with my friends Julie and Jen on the Amalfi Coast!