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Medieval Towns, Wine Tasting in Tuscany, & Caroline Makes an Oopsie

One of my favorite days in Europe was thisclose to not having had happened at all due to a tiny, minor, little itty bitty oopsie I made. Don't judge too hard.

I'll remind you that Cassandra and I aren't the planning type of people. As in, not only did we forgo transportation arrangements in Venice, but we also neglected to schedule activities for Florence. This led to us arriving in the early evening and spending two hours on the phone with every tour company listed on Google, Cassandra speaking in Italiglish, trying her very best to get a tour operator to take pity on us and bring us to wine country the next morning.

That was hiccup #1, but lo and behold someone was nice enough to squeeze us in and told us to meet them at 9am sharpish. We ate, drank, indulged in gelato, watched some fireworks. I twisted the lock on the front door a couple of times, and called it an early night.

*flashing lights* WARNING: HICCUP #2. You see, European locks sometimes have an attitude, and in the act of "twisting the lock a couple of times," I unknowingly deadlocked us inside of the apartment. All morning. A locksmith had to be called. Go ahead and laugh. We did. Until we almost cried, because first of all how in the world, and also, our wine tour left two hours ago.
Funny how these things go, though, because our tour company found the tale to be entertaining enough that they sent a separate car for us, a little nine-year-old Italian charmer included. Our driver sped through the rolling hills of Tuscany, treating us to blurred panoramas of green and blue, until at last the car screeched to a stop at the outskirts of a walled city where we stumbled out...

and were treated to this view:
Murmuring over the pretty little sight in front of us and adjusting our lenses this way and that, we reluctantly moved forward when our tour guide nudged us along. Better things ahead, he promised. He led us through the sloping streets of the medieval city of San Gimignano, pointing out this tall tower and that torture museum and here's an artisan market of lace dresses and football jerseys galore, and ahhhh...
award-winning gelato.

How could one say no to that?
(The last time I focused this hard, I'm pretty sure was in high school when I didn't understand a single question on a Calculus test and tried to will answers to appear. The gelato was much kinder to me, thankfully.)

Satisfied that he got some sugar in us, our tour guide encouraged us to wander the town on our own and pointed us towards a lookout with a breathtaking view.

I'm telling you, I stood at that ledge trying to memorize every curve of the earth, every tiled roof, every meeting of cornflower with dusty taupe with kingfisher with terracotta with emerald. It was stunning to a point where I felt obliged to express a little vocal gratitude for this beautiful country, this beautiful planet.

//end cheesefest. Onto consumerism. Kelly insisted on some shopping:
and so did Cassandra, of course.
Having met up with the rest of our wine tasting tour group, we were ushered back to our private car (followed closely by our tourmates on Vespas! We should take some lessons from them on planning a proper Italian vacation!) and zigged and zagged and frighteningly zoomed to our first winery of the day.
Time is warped in this winery, my friends.

We spent no less than three or four hours in its confines, but it felt no more than thirty minutes. A charming Italian fella with the heaviest of accents walked us through the proper steps of wine-tasting. Reach with your left hand, pass it to your right hand and hold the bottom of the stem with two fingers, take a deep sniff, swirl it this way and that, observe it, take a sip, vibrate your lips with your teeth (yes), and then swallow and experience.

They poured us glass after glass, here's a white, here's a couple of reds (ooh? could we revisit that one, sir?), a delightful Brunello, a couple of Chianti Classico's, don't listen to me because I'm a negative expert on wine and am only trying to sound passable right now. Salamis, salads, a hearty veggie soup, breads, cheese, and!
Theeeeeeeee most amazing lasagna. At this point, the charming sommelier was telling us about the, ahem, the aphrodisiacal qualities of a good truffle oil and he walked right on over to us all, "accidentally" tipping over the truffle oil and drowning our lasagna in it.

Hot. dang.
Our sommelier, like I said, was quite the flirt (and an Adam Scott lookalike!) and perhaps emboldened by the knowledge that the rest of us all were very much still guzzling wine like we were camels in a desert, whisked this one away:
with the promise of biscotti soaked in port, and an Italian love affair if she were so willing! Alas, she agreed to the former and asked for a raincheck for the latter. After all, there was a whole 'nother winery waiting for us, sir!

Exiting that first winery, we were surprised to find the sky still so blindingly bright and ourselves so... truth be told, so lacking balance and good sense.

"ANIMALS! GO TAKE A PICTURE!" I demanded of my roommate.

She obliged.
... and then took it one step further.

"For the blog," she made sure to note graciously.
Fearing that we were still in need of some wine (not the case, I assure you), our driver literally slammed his foot down on the gas – at one point, I saw that we were whizzing through Tuscany at a terrifying 120 km/hr – and jerked the steering wheel this way and that, adeptly reaching over to fiddle with the stick shift every now and then. Oh, Italians. To his credit, I survived, didn't I?

There was also a moment of amazing clarity for me as my hair whipped in the wind and the world became nothing more than a blur of colors and sound. It was one of the most tangible instances of true joy – along with that one afternoon along the Seine – I can ever remember having.

To the next winery we go!
Down the dusty path we ambled, to the wine cellar where everyone else listened intently, and Cassandra and I giggled and posed and pet some livestock and heard nary a word.
Then, they left us with some wine at some picnic tables, where we nibbled on cheese and olives, pushed our friendly tour guide to teach us more Italian and tell us about his upcoming nuptials and his travels and enjoyed this view of San Gimignano, our starting point:
What started out as a day with plenty of hiccups, came to a close with nothing but a tipsy stupor and lots of good vibes. Tuscany, you're somethin' else.
What has been your favorite wine-tasting experience? Where do you want to go?


  1. first- could y'all have looked any cuter?! this is so much fun! I'm so jealous.

  2. Totally jealous right now! Wine in Italy, what could be better?! And it seems like you and your friend had a great time from start to finish, aside from getting locked in, haha. What's an adventure without a few bumps on the road, literally?

    1. Ha, I believe in the philosophy that the bumps in the road are what make the ride so fun. Just wait until you hear about Naples! :)

  3. I'm sorry, but I just had to do you get locked in the apartment?!?! hahaha but sometimes those locks are tricky!!!


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xx Caroline