My 48 hour weekend getaway in Tuscany was a particularly special one. It was my last trip before returning to Milan (my home for the past 9 months) and finally heading back to LA.
Firstly, I have to emphasize that there is so much more to Tuscany than just Florence. Don’t get me wrong, Florence is a beautiful and romantic city entirely deserving of its reputation. BUT living in Italy, I discovered just how much the country truly has to offer, and that it's all about the hidden gems and oftentimes lesser known destinations that make exploring Italy so special.
Stay
We were lucky to find the perfect little airbnb oasis. Our host, Candida, was incredibly sweet, and I would 1000% recommend staying at her charming home in San Casciano Val di Pesa. Her homemade jams and hot baked goods in the morning made for the ultimate al fresco breakfast, and chatting with Candida about her extended trip to South America was such a treat (she even shared her photos with us).
We arrived at our airbnb past lunchtime and were famished. Candida provided a few nearby recommendations and we ended up at a quaint little restaurant called Cinque di Vino.
San Gimignano
After lunch, we headed straight to San Gimignano, a medieval hillside town.
A big highlight for me was the gelato shop in the main square, Piazza della Cisterna. You don't want to miss out on Gelateria Dondoli for some seriously delicious gelato and some pretty unique flavors. I tend to be a little boring, sticking to the classics, but my boyfriend has a much more adventurous palate. He chose basil cheesecake swirled with strawberry and tomato sauce and a crumble. It was odd and unexpected, but actually quite good. I don't remember the exact flavor combination I chose, but they were all pretty shades of light pink. Perhaps the most exotic flavor I selected was "grapefruit with champagne", but I assure you, they were all scrumptious.
Shop
I wandered into Uashmama, a cute little shop that sells their namesake brand's handcrafted paper bags. I really love to find unique locally produced items when traveling, and this Tuscan brand would have made for some perfect gifts. I kind of regret not getting a little souvenir to take back home.
Eat
My original plan was to score a reservation for a sunset dinner at the Tuscan vineyard, Fattoria Poggio Alloro. The tripadvisor reviews were excellent, and I had my heart set on trying their Saturday steak night. Unfortunately they were fully booked, and I was utterly disappointed. Our actual dinner wasn't anything to write home about, so I'll just leave it at that.
Abbazia di San Galgano
Day two was a bit of a late start. We were pretty exhausted from the long drive and previous day's adventures, but after breakfast we were ready to head to the Abbazia di San Galgano. The abbey is a really interesting site to see. I've personally never seen anything like it. For anyone else that loves beautiful, abandoned spaces, this roofless former church is the perfect visit.
Siena
After having lunch near the abbey, we headed to our final destination in Tuscany: Siena. I would say one of the most unique features of Siena is the large central square, Piazza del Campo. The square is famous for its biannual horse race called the Palio di Siena, and it's different from any other main square I've seen during my time in Italy (mainly for its size and downward slope). It makes for the perfect spot to sit down for a drink and watch the time go by. While we weren't there during the races, our timing seemed to be serendipitous as we happened to be there for a flag ceremony, with a procession of boys and men of all ages dressed in traditional attire. I wish I could tell you what it was for, but if you happen to know the story behind this tradition, please do share! I believe it was related to the horse races if that helps.
See
If you love the cathedral in Florence, you're sure to be just as obsessed with the cathedral of Siena. Visiting cathedrals and churches became somewhat of a habit during my time in Italy. There's truly nothing like these old cities and buildings at home in the US/ Los Angeles, not even close.
One random turn after another, we made our way to what ended up being my favorite spot of the day. I wish I could tell you how we got there, but we accidentally ended up next to the Basilica di San Domenico. I can't stress enough the beauty of wandering and getting "lost" as we did, to find the most incredible views of the city. Hopefully you get a chance to catch the views at golden hour, but if you happen to miss it, the city is also wonderfully magical in the evening as the streetlights cast a warm glow along the narrow alleys.
Eat
We ended our evening in Siena with dinner at Osteria Il Carroccio, discovered using my trusty travel guide, Instagram. The prices were very reasonable, and I loved the gnocchetti al pesto di cavolo nero con tartufo (gnocchi with kale pesto and shaved truffles).
Transportation
I would definitely recommend renting a car to explore Tuscany. There's so much to see, and it's not so easy without a reliable way to get around. Once you get to your destination, I think the best way to explore a city is to wander on foot. There's something so special about finding a small, pretty street or old building that feels like a secret yet to be discovered.
Etc.
Most of us probably hear Tuscany and think Florence and Tuscany are synonymous, but Tuscany is a pretty large region with tons of unique cities and landscapes, including the seaside! I am dying to return to Tuscany. There's so much I didn't have the time to see or do during my short weekend trip.
I was most disappointed about not being able to visit an organic farm. For those who don't yet know me well enough, let me explain. I am two very different people at the same time. I am a girl that loves the hustle and bustle of a big city with unlimited resources and fun things to do, but I am also a girl that fantasizes about living in a country house, growing my own veggies, and having cute little farm animals. And for this reason, I was specifically hoping to experience Tenuta di Spannocchia.
I discovered Tenuta di Spannocchia how I discover most things when doing a bit of travel research: Instagram. I wish I could remember exactly how I stumbled upon this lovely little farm, but it was most likely down the usual Instagram rabbit hole. The farm is not just a farm, but also a bed and breakfast where you can stay and even take cooking classes. If I'm not mistaken, I had come across a photo of someone baking bread in a wood fired oven (*drool). Even more, I found that they offer a unique program where you are given an opportunity to stay and work on the farm. You can learn more about that here. It seriously seems like such a dream.
If you ever have the pleasure of visiting, please let me know how it is!
