An American Bum in Tuscany

Way back in the spring, Tom and I were both job hunting and he promised me that once he got a new job, he’d take me to Italy. It sounded like a great idea at the time, because shortly after, I got a new job breaking down boxes, which wasn’t great but meant I wasn’t a total bum and two weeks after that, Tom got a new job too. We were both like, “Yeah! New jobs! Let’s go to Italy!” We began to plan the trip, adding Italy onto the end of a trip to London for a friend’s wedding and spent two weeks and a pretty penny booking flights, hotels, AirBnb’s and coordinating with my friends Julia and Sam to meet up with them in Cinque Terre. It was all great and exciting. At work, I surreptitiously put it in the team calendar, blocking out nine whole days with the words, “BETTY OOO,” though of course I couldn’t wait for people to notice and ask, so I could say smugly, “Oh, my boyfriend is taking me to Italy.”

And then I got fired. Any sign of my ever having been on the team calendar was erased. Any sign that I was ever at the company was erased. They took my badge, my computer and asked me to leave all under half an hour. All I had time to take were three blue pens (ironically now my favorite pens). I was bummed for a hot second – not least because my stupid ex-coworkers would never know that I was going to Italy – until I told myself to look on the bright side: while I didn’t have a ton of job prospects to look forward to, I was still going to London and Italy.

But traveling is never cheap (unless you lie to yourself with “staycations”), and despite how the universe should work, traveling without a job doesn’t make it cheaper. But economically in general, it was still a good time to go to Italy. Especially if, like me, you’re bad at math. Someone told me the Euro was 20% cheaper so I went around thinking, “100 Euros? That’s 80 dollars.”

Everything 20 percent off!

Anyway, despite my parents (and probably everyone else) wondering what the hell I was doing with my life and Tom wondering why he was taking his bum of a girlfriend around Italy, I still thought it was a great idea. And now, some photos from our trip! 

The road into Tuscany.
The road into Tuscany.

I asked Tom today why he chose Montalcino in Tuscany aside from all the other places we could have gone, and he said, “I dunno, it looked cool.”

Very cool.
Very cool.
Kind of cool.

Ostensibly, we went for the wine and Tom had made all the bookings, reserving two spots at two wineries, but we drank a bit too much with our late dinner the night before at Il Grappola Blu and didn’t make it to either. If you read my post on our trip to London, you’re probably wondering, “What the hell do you guys do when you travel?” I don’t know, but it seems like a lot. And thankfully, there were other ways to taste wine, which you can read about in more detail here.

We flew into Rome, picked up our rental car which was not a Fiat as we had reserved but a Ford, but thank God since the GPS spoke English. Later, we’d meet another American couple who didn’t know how to change their Fiat’s Italian GPS into English and spent much of their trip, it sounded, getting lost. And then we drove three hours north to Tuscany.

We stayed two nights in Montalcino before heading to Cinque Terre, but after this trip Tom and I came up with a new travel rule: at least three nights in each spot. This is especially important when you have long travel days bookending each destination. Montalcino and its surrounding towns were small, but we spent so much time driving from spot to spot that it still felt somewhat rushed.

Walking around Pienza, also
Walking around Pienza, also “cool.”

The next morning, our winery tours missed, we drove to Pienza, the “Ideal City” as called by some enlightened folks during the Renaissance, where we lunched and shopped around, and then attempted to see the remains of a medieval fortress called the Rocca d’Orcia. But it was closed, so we hung around the locked gates and like a couple of losers and then went back to Montalcino for our last evening. 

Rocca d'Orcia, from a distance.
Rocca d’Orcia, from a distance.

Back in Montalcino, we wandered around and tasted some wine, which was the plan all along.

We could have spent one more day there, but it’s okay we made out with a lot of wine to carry us through ’til next time.

The view from Enotecca di Piazza was better than our view at dinner.
The view from Enotecca di Piazza was better than our view at dinner.

Address Book
Stay: Palazzina Cesira – A Bed and Breakfast owned by an American man and his Italian wife. Awesome breakfast and huge rooms.
Eat: Pienza – Ristorante Dal Falco and Gelateria Toscana. Montalcino: Taverna Il Grappola Blu (Italian home cooking) and Enoteca Osteria Osticcio (Stuffy Italian with their own wine shop, but we did not find it that stuffy); Why Not Gelateria.
Shop: Pienza –Altroieri for table and kitchen linens, some clothes; Officine904 for Italian leather goods you won’t find in the States. Montalcino – Farmacia Salvioni 1905 (though this is a chain) for Italian soaps and skincare; For wine: Villa Le Prata Showroom and Enotecca di Piazza.

Also: Thom’s Thursday Thoughts on Italy and What Does It Mean to be “Cultured?” (Having gone to Italy, duh).

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