In Tuscany, A Traveler’s Dream Day (Part 2)

From Florence to San Gimignano, then to Siena – yes, this was just the start of an incredible travel day through some of Italy’s most beloved cities.

As I was saying in Part 1, Lucas and I had set off before 6am with a plan to see all that we possibly could in one day, and that meant not stopping. Sure I could have checked into my room and relaxed, gone for an evening stroll and dinner, met a friendly italian girl, who knows….but that was not the plan! This day was about travel and more travel!

Siena is superb. It’s an interesting city and one that unfortunately gets forgotten in the haste or necessity to visit Florence and then move on from Tuscany. But really, for anyone visiting Tuscany for more than 2 or 3 days, Siena is a perfect home base. Why? It’s the place you’ll want to explore and then, from time to time, hop onto a bus or train to venture out into the nearby wine towns which add much of the unfettered beauty of Tuscany’s terrain.


With heavy bags and rain hoods up, we walked with purpose through Siena’s streets. In the distance we saw our target – a tower which stood out clear to all – the Duomo di Siena, (the Cathedral of Siena).

Walking quickly while trying to still take it all in, we could not help but notice the juxtaposition between modern vs. medieval. Everywhere the divide between present day and all that comes with it – electricity, wifi, mobile devices, and (sigh) Snapchat, could be seen against the backdrop of what once was a great city and a greatly important city for Italy.

Don’t get me wrong. Siena is beautiful and like most all of Tuscany, fully preserved. There is however something slightly unsettling about standing next to a cathedral built in something like the year 1215  and admiring a window to a previous world – then seeing a flashing green pharmacy sign and glass doors slide open as a fresh-faced tourist trots out with a Gatorade and Snickers bar in hand.


The Piazza del Campo is a remarkable public square. It’s the center of the town, a landmark, a hangout, postcard ready, the meeting spot, and more. Definitely worth seeing during the day and at night. It also happens to hold one of the wildest horse races you’ve never been to, called the Palio di Siena.

For us, standing in the square was lovely but the rain was threatening.

With the rain picking up a few parse groups of tourists flashed their photos but Lucas and I opted for a celebratory beer at one of the covered tables along the square. A cold beer in hand, we bounced from story to story, recounting what we had seen and done the days before. When he asked, “And what will you do next?”. I replied slowly, first looking over the unfolded map and then the bus schedules, “Montalcino? For the wine I suppose”.

From Florence to San Gimignano, then to Siena – I had hit three incredible cities, and yet this was just the start. Montalcino was waiting.


We said goodbye with a quick hug and a smile, I grabbed my bag and took off in direction for my hotel for the evening. I needed to check in to my hotel and then try and make it to my bus in half an hour. I had to move quick!


Check in time. I had reserved a well ranked room just off the main drag, maybe 10 minutes from the plaza, and after walking up the stairs, I took the quick tour with Francesco, the proprietor of this small 10-15 person hotel which felt much like a bed and breakfast. My room was a brilliant step up from the tiny hostel beds and cramped quarters in Florence, oh yes tonight I would sleep like a baby!

Time was working against the plan so I tossed my bag on the bed, pouring out all contents – rummaged around for a smaller bag and then bolted out the door for the next adventure of the day with a wave and a slam of the door.


After some serious speed walking and even a semi-jog, of course, then a pit stop to grab a coffee and a panini for the road, I boarded the bus and reclined back with the tunes bumping from my ipod. Half asleep, I leafed through a guidebook and pamphlet to better understand what I would find in Montalcino.

The guidebooks talk and talk of the famous wine, Brunello di Montalcino, and so as the bus tumbled through beautiful countryside, racing against the slowly dipping sun, I took a swig of water and got ready for wine tasting.


The town was incredible. Tucked up into the hillside, like a spire with a difficult to ascend staircase, the top was all mine.

Montalcino was quite and empty, clearly I had arrived weeks well before the tourist rush. The shops were open but unclogged with my wide-waisted fellow countrymen and roaming Europeans, I had open rein. The town was mine. Yes, for the afternoon I would stroll and snack, and wine taste in sweet, sweet solace!

After a quick, fortifying cappuccino and almond & orange pastry, I followed the signs up to a bell tower or something of the sort and just admired what a truly beautiful and isolated town I had found. Next to do was of course, sample some of the local wine.

With a great back story you can get away with almost anything. After mentioning, I was looking for a nice medium priced bottle of wine – to bring as a thank you present to my friend’s home the following day – I was previewed and offered tasty swigs of countless varieties and styles of regional wine. An American couple walked into the wine shop to find the owner pouring me, what must have been 8 or 9 different glasses of wine. The two of us hunched over like conspiring jewel thieves: inspecting each glass for any flaws, then sniffing and swirling wines. The couple looked around the and seemed to afraid to ask or sample so I broke in, made a comment or some sort of noise to get the introductory conversations going, and within moments, they joined in, drinking the wines and working up a nice buzz.

The rosso, a beloved staple, is a slightly spicy and young red wine which everyone in the town serves up for any occasion. It is sweet and sour and just seems to be the type of wine you would love to chug down while on a hilly hike or at any point with a nice hunk of bread and salami. Always after, I’d be given a sample of the Brunello, the older brother with an attitude. It’s made from the same grapes as the rosso, but it according to the rules, it must be aged 5 years and it takes on a powerful, grappa-like, kick. All that sitting and aging for 5 years brings the big Brunello all the way up to 15% or 16% alcohol.

After several different wine shops, without question, I was teetering near drunk and running low on energy. The sun was sinking fast towards the horizon, so I picked a bottle, paid the nice man, and briskly made my way to the bus stop.

I saw the American couple strolling by, we all hugged for unknown reasons to say goodbye (ah the Brunello!) and I curled up in my bus seat and listened to Volare and my italian bus mix.

An hour and a half later, the evening was approaching and Siena took on a whole new feel.


At my historic little bed and breakfast, I felt like a part of the Nobility, opening my wooden shutters to gaze out at the city and admire the evening. To prepare for the evening encore, a nice dinner with vin. I enjoyed a sudsy warm shower and then strolled the cold cobblestone streets with my hair slicked back and a good book tucked under my arm.


After a revitalizing, near arctic cold, evening stroll and a bit of window gazing,  I found myself back right near my hotel. Down a back alley, was an idyllic looking Trattoria restaurant with a welcoming yellow light out front. Entering, I had assumed the dinner hours were the same as in Spain, where I had been living for more than a year. Quite wrong. In fact it seemed, I was a bit later than most. A few tables were finishing dessert, one or two still eating a main, and the hostess sat me back in the corner to enjoy a nice quite meal.

I ordered the best pasta I’ve ever had, a simple pasta in puttanesca sauce – a salty mix of olive and caper taste, and washed it down with a couple of glasses of ripe Rosso. A tiramisu and an accompanying espresso to finish only seemed right.


Full and tipsy, I made my way around town like a Friar, belching and in search of a comfy place to lay my worn out body.

Back at my comfortable room, I flipped through italian TV (mostly black and white movies and strange news channels) and enjoyed 3 bottles of Moretti beer before passing out.

Looking back now, it was a wondrous day but what stands out is that I managed to see so many great cities and experience so much in one day.

Yes, I think it’s safe to say that day through Tuscany may be the best travel day I have had…yet.


A Few Photos 




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