Wine, Cheese, and Mild Confusion

So our final day in my beloved Florence arrived… and I was already sad to leave the city... but I had no idea it would turn out as rough as it did. Something strange happened to me on my final morning... I got "dizzy."

Was it perhaps the cause of excessive amounts of wine window Aperol Spritzes?

No.

At least I don't think so.

My dizzy was not your average “stood up too fast” or "overindulged" dizzy... but the full-on spinning room of doom dizzy. Ya. Not fun.

During that final Florence night, I woke up several times (as per the usual), and no matter how hard I tried, I couldn’t fall back asleep. But that wasn’t even the worst part. The absolute 'nightmare' (for lack of a better word) started early in the morning. Every time I shifted my position in bed... left side, right side, even flat on my back... my head went into a chaotic spin. I couldn’t focus, couldn’t see straight… it was like my whole head had been put into a blender.

I’ve never experienced anything like that before... and honestly... it frightened me. My first thought? ... “Well, this is it... my brain is officially giving up in Italy.”

Immediately, I resorted to obtaining my PhD in Google/ChatGPT self-diagnosis research and learned that apparently, the tiny crystals in my inner ear might be “out of place.” Whatever that means. I think I have Benign Paroxysmal Positional Vertigo...

So here I am... hoping the world stops spinning soon.

Other than that woozy fiasco, it was honestly so hard to leave Florence. I really, truly love that city... and their church, as odd as it is to admit that.

ZC and I went out for our final breakfast before heading to the station to catch our train to Siena. Now, ZC is… let’s say, a bit more punctuality-enthusiastic than I am. She likes to be places early. Sometimes too early. Whereas I’m perfectly content to roll in a casual 10/15 minutes before departure... sometimes less. When I say this... I mean ZERO disrespect... though it was taken by some as a horrible thing to say. I have my little quirks too...

Thankfully, we didn't have too much time to waste, as the train was right on time. I was utterly exhausted after a sleepless, dizzy night and desperately needed rest. Now, as I have mentioned before, Italian trains aren’t exactly known for their sleep-friendly comfort, but somehow I managed to steal a few minutes of neck-wrenching shut-eye.

Not long afterwards, we arrived in Siena. I had forgotten entirely... or maybe never fully realized... just how hilly Siena is. When I visited before, I think I stayed right in the centre, so I probably didn’t experience the full rollercoaster workout of the city's outskirts.

From the train station up to the bus station, we took nine... yes, nine... escalators up. One of them wasn’t working, my luck, so we had to lug our bags up a steep flight of stairs.

Another solid point for Team Backpack.

ZC was staying in an Airbnb on the outskirts of Siena. The place itself was nice enough... clean, spacious, quiet (well… more on that in a minute) but not exactly the rustic, cozy Italian hideaway I’d pictured. After years of being obsessed with The English Patient and Under the Tuscan Sun, I’d imagined something far more romantic... perhaps a crumbling brick monastery or a little stone homestead with vines climbing the walls and golden light spilling across the terrace at sunset. When I think of Italy, I tend to envision terracotta walls, wooden shutters, uneven tile floors, heavy wooden tables, mismatched chairs, and shelves filled with olive oil and red wine...

No. It wasn't like that.

What it did have, though, was dogs. Lots of them.

Apparently, the elderly lady downstairs owns EIGHT chihuahuas. I kid you not. Maybe more.

They bark constantly. Not your average “someone’s at the door” bark... we’re talking nonstop, high-pitched chaos. ZC told me she’s tried to go outside and enjoy the veranda a few times, only to be forced back inside by the relentless yapping. I told her she has an obligation to mention it in her review for other travellers coming to this area. Nowhere in the listing did they mention anything about a chorus of chihuahuas living on-site. I mean, that’s something others definitely deserve a heads-up about.

Don’t you agree?

Over the past couple of days, ZC and I have been off exploring the Tuscan countryside.

I will give a little synopsis of each city...

San Gimignano

Known as the “Medieval Manhattan” for its iconic skyline of stone towers, San Gimignano was a prosperous town along the Via Francigena pilgrimage route during the Middle Ages. Its wealth came from saffron trade and banking, and many of its 14 surviving towers were symbols of family power. Today, it’s a UNESCO World Heritage Site famous for its medieval architecture, Vernaccia wine, and stunning hilltop views.

I think I’ve been here before... hard to say. My memory is… unreliable at best. Maybe it’s travel fatigue, or maybe I’ve managed to outsource my 'remembering' to my various travel books and blogs. Either way, I don't know.

Just the other day, I was saying how baffled I am by people who travel and somehow remember everything... every sight, every building, every meal, every person they met and every conversation they had.

I don’t.

I mean, of course, I remember the beauty, the way a place made me feel, and the larger moments that stand out… but the more minor details often seem to slip away.

I’m not sure whether that’s because my memory is simply bad or because, once I write something down, the words take custody of the memory. Or maybe it’s just what happens when you travel too much, when your mind gets filled to the brim with impressions and sunsets and stories and sights... and there’s no more room left for the other things. I never want to be that person who travels too much and forgets the intricate details of each trip... but unfortunately, it does happen. To me, anyway. Good thing I write everything down. I always have.

I need to go back and read my old travel memory books.

I will... soon.

There is a lot of lavender in Tuscany. Is lavender a thing around here? I don't think I ever knew that. Olive oil? Yes. Wine? Yes. Sunflowers? Yes. Lavender... ? Interesting. A lady, in one of the shops, handed me a marketing brochure sprayed with lavender... and now my bag smells amazing... like calmness and fresh laundry.

Obviously, you can’t be in Italy without overindulging in gelato. After lunch, we’ve taken to enjoying a scoop (or two) of fresh, delicious ice cream. In San Gimignano, the Piazza della Cisterna had two gelaterias vying for attention... one with an enormous sign proudly claiming the award for “Best Gelato of 2024,” and the other with an equally large sign boldly declaring it had “The Best Ice Cream in the World.”

Which one do we choose? That was the million-dollar question.

We ended up at the one without the absurdly long lineup... the self-proclaimed “best ice cream in the world.” And honestly? They weren’t lying. Go figure.

Monteriggioni

A perfectly preserved walled fortress town, Monteriggioni was built in the early 13th century by the Sienese to defend against Florence. Its circular walls and 14 watchtowers still stand almost exactly as they did centuries ago, giving visitors the feeling of walking straight into the Middle Ages. Dante even referenced it in 'The Divine Comedy.'

The town of Monteriggioni was pretty much picture-perfect: cobblestone streets, a little church, old stone walls, and charming shops. We wandered around, letting the streets work their magic, soaking in the quaint charm and the centuries of history .

As we exited the main tower gate, I immediately thought, "THIS would make a fabulous photo." I was right. Looking one way, you could see the charm of the village entrance, cobblestones, and walls... and looking the other, the Tuscan valley stretched as far as the eye could see.

The only problem?

Two bikers decided to exit the main tower gate at exactly the same time as us. Just as I stepped forward from the arch to frame my shot, they stopped. Right in the middle of the archway. WITH THEIR DAMN BIKES! Not moving. As they stood there chatting, the woman decided it was the perfect moment to answer her phone... right in the middle of my photo shoot. A spectacular photo spot... to be clear, not just for me, but for everyone visiting Moeriggioni... but now completely blocked. By them.

I politely planted myself directly in front of them, camera in hand, waiting for them to move. They didn't. All they had to do was roll about ten meters down. Easy.

But no.

I’m not sure if they were even aware of me standing there, waiting, or just completely oblivious. Either way, I got stubborn... and pissed off. I was NOT moving until they did. The woman... clearly North American... rambled on the phone with her daughter, gushing about her outfit and how silly she looked “like a gypsy.” The man? I don't think he was the father because he was totally disengaged in the phone conversation and had a different accent.

They didn’t budge.

Finally, she ended the call, but instead of leaving, they decided this exact spot was the perfect place for their little biking photo shoot. The plan? He’d film her biking down from the village and through the arch. My perfect shot… now theirs.

JERKS.

By that point, after waiting forever, ZC had had enough. She suggested we ruin their little photo shoot, and I was immediately on board. Casually, she started walking back toward the arch and into the village… right through their frame, effectively wrecking their biking video.

The man started shouting, “Signora! Signora!” but ZC ignored him, slowing down even more as she meandered up the cobblestone street.

I think they only realized what had happened afterward. Me standing there with a smirk on my face.

Yeah… screw them.

I get annoyed with people. Seriously. Tourists should show respect when someone else is trying to be a tourist too. In my humble opinion...

Castellina in Chianti

Nestled in the heart of Chianti wine country, Castellina has Etruscan origins and medieval charm in equal measure. Once a strategic fortress between Florence and Siena, it’s now a peaceful village surrounded by vineyards and olive groves. Visitors come for its underground Via delle Volte passage, rustic wine cellars, and classic Tuscan atmosphere.

The only reason we ended up here was because I’m hopeless at following the blue dot on Google Maps. I was actually trying to find a town called Fonterutoli (I think we drove right past it, actually)... and well, I got completely disoriented.

Somehow, we ended up at Castellina in Chianti instead.

But it actually worked out perfectly. We were right in the heart of the Chianti district... a must-visit in Tuscany and home of the famous black rooster.

I had been to the Chianti district before, but of course, I forgot everything I learned.

Typical.

Here’s a quick rundown from my “extensive” research on the black rooster…

The black rooster, or Gallo Nero, has been a symbol of Chianti since the 13th century. Legend has it that towns in the Chianti region used roosters to decide the borders between Florence and Siena. The clever locals supposedly starved their rooster so it would crow earlier, giving them an advantage.

Nowadays, the black rooster on bottles of Chianti Classico wine is a mark of quality, showing the wine comes from the historic Chianti area, is made with Sangiovese grapes, and follows traditional rules.

It was cold. We thought we were just stepping out of the car to snap a quick picture of the black rooster... but somehow we ended up wandering through the charming little village and stopping for a glass of wine.

The downside? Spending more time outside than we planned… without jackets. ZC ended up catching a cold...

Montepulciano

A Renaissance gem perched on a ridge in southern Tuscany, Montepulciano is known for its elegant palaces, sweeping vistas, and world-class red wine, Vino Nobile di Montepulciano. The town flourished under the Medici family and boasts architecture by major Florentine artists. Walking its steep streets feels like stepping back into a 16th-century painting.

I knew I had definitely been here before… but that was about it. I remembered the beautiful hilltop setting. Parking was a bit of a struggle... no surprise, given how stunning the place is... and tourists were everywhere... even at the end of October.

We spent about an hour wandering uphill through the winding streets. Our first stop was a shop with an old Etruscan tomb to explore... and we finished with a wine tasting and some (not so vegetarian) treats. Had we been meat-eaters, the spread would have been impressive and could have easily replaced lunch. Sheeses, salami, truffle cream cheese on bread, ground beef with sundried tomatoes, crisps... and honestly, so much more than one would expect at the end of a free tomb tour!

We have taken to making our own lunches on these day out, Tuscan excursions. I'm trying my best to be a true budget traveller right now... and fighting off the urge to buy trinkets and souvenirs. This, obviously, frees up finances for gelato, wine and Aperol Spritzes. Priorities. Right?

I really do love these old villages. There’s something about the history, the cobblestones, and the views that never gets old.

Pienza

Designed by Pope Pius II in the 15th century as an ideal Renaissance town, Pienza is often called the “Pearl of the Val d’Orcia.” Its harmonious layout reflects early humanist urban planning, blending beauty, symmetry, and practicality. It’s also famous for its pecorino cheese and breathtaking views of the surrounding valley.

Speaking of pecorino cheese... we could smell it everywhere!!

Pienza was much larger than the other villages we’d visited... though equally beautiful, and with its very own share of history. At one point, we tried to pop into a wee spot for a glass of wine... and to charge my phone (still… always travelling with a dead battery), but we got gently shooed away. Turns out, it’s a proper restaurant.

Oh. Ok...

ZC had mentioned that she heard that Italy has different types of restaurants, each with its own “status” or vibe. Naturally, I had to look it up…

1. Ristorante

Traditional sit-down restaurant, often more formal / Offers a full menu with multiple courses / Prices tend to be higher.

2. Trattoria

More casual than a ristorante, usually family-run / Focuses on local, regional dishes / Hearty, home-style meals at reasonable prices.

3. Osteria

Historically a place for wine & simple food / Casual, often focuses on local specialties / Smaller menu, cozy atmosphere.

4. Pizzeria

Specializes in pizza, sometimes pasta or salads / Casual or more upscale, but typically very laid-back.

5. Enoteca

Wine bar that may serve small plates or snacks (cichetti) / Focuses on wine tasting & local specialties.

6. Caffè / Bar

Serve coffee, pastries, and sometimes light sandwiches / Casual or a social hub.

So, obviously, a ristorante wasn’t exactly the place to stop and charge my phone. Lesson learned.

San Quirico d’Orcia

This charming medieval village sits in the heart of the Val d’Orcia and was once a key stop along the Via Francigena pilgrimage route. Its well-preserved walls, Romanesque churches, and tranquil gardens reflect centuries of Tuscan history. Today, it’s loved for its quiet authenticity and proximity to some of the region’s most photographed landscapes.

We only stumbled across this little spot because we were looking for something on the way back to Siena... and it was still quite early in the day. After a bit of online research, Google recommended this sleepy little village, and I’m so glad it did. The village was tiny, but absolutely charming to wander through, especially with a bowl of delicious gelato in hand to cap off a perfect day of sightseeing in the Tuscan countryside.

Tuscany is just… gorgeous. Rolling hills, cypress trees, fall colours, wine tastings, and every day is a whole new level of “the best gelato in the world” experience. I could easily get used to hanging around here.

Even when I’m dizzy, lost, and blindly following the little blue dot in the wrong direction… I still love it.

Giuseppe Verdi once wrote, “You may have the universe if I may have Italy.”

I get it.