Last month I had the chance to spend some time in the beautiful region of Tuscany. After spending time in Florence with my family, I had a couple days on my own to kill before a yoga retreat I was attending in Cortona. Initially I planned on spending those days in Florence, as it seemed like the easiest solution. But the more I realized how close I was to Tuscany, I felt like it would be a missed opportunity not to go. So I set aside my fear of driving in Italy, rented a car + took a little Italian road trip. I'm so happy that I did.
Tuscany is a pretty large region, and all of it is stunning. There is SO much to see and do that I can't even begin to fit it all into a singular guide (guess I'll just have to take some more trips back!) But even in the short time I spent here, there's so much to recommend to you I don't even know where to start! For starters, let's talk about the best time of year to go to Tuscany and what to pack for a trip to the Italian countryside:
Fall was the perfect time to visit Tuscany. For one, it's when harvest season is (which is always a fun time to visit any wine region for the full experience). Aside from that though, the weather is ideal. While the climate is generally pretty mild, average temperatures in the fall are in the 60s (perfect sweater weather). Should you choose to visit then, here's what I'd recommend packing.
Given the mild climate and crisp air, ponchos are the perfect uniform for Tuscany: cozy + layer-able, yet chic + pulled together. Whether you opt for one that's a pullover (like here, here and here) or one that has an open front (like here, here, here and here) you'll be glad you packed this staple to wrap up in.
I love the way a wool hat (here, here, here or here) looks paired with a poncho. There's just something about wearing a hat in general that makes me instantly feel more put together (which is convenient, because there' something about drinking copious amounts of wine makes me feel quite the opposite...)
While Tuscany didn't involve much walking for me (I was mainly in the car or staying within the properties where I stayed) there's no need to pack your heels. Flat, comfortable boots are an ideal option (both comfortable and still polished). I'd bring at least one pair of ankle boots (also here, here and here) as well as some knee-high or over-the-knee boots (also here).
You're going to want to bring back wine (and lots of it). While you can ship back to the states, it would be a missed opportunity to not fit as much as you can back in your checked bag. To protect your precious Tuscan wine, make sure you have a hard shell suitcase! I brought my DVF luggage (similar here) but also love pieces like this, this or this.
In terms of where you should go in Tuscany, there are more options than you can even begin to imagine. While I did venture out to some other areas like Montepulciano and Cortona (which were both wonderful and also definitely worth visiting) my favorite experiences that I would highly recommend prioritizing are Castello Banfi and Fonte de’ Medici.
Nestled in the Tuscan countryside not far from the quaint town of Montalcino, you'll find Castello Banfi, a historic fortress surrounded by vineyards and olive groves. The Banfi family is passionately dedicated to making prestigious Tuscan wines (they’re a large producer, so chances are you’ve heard of them before). First and foremost, you can visit their Enoteca/Wine bar, which recreates the atmosphere of a true Tuscan wine shop. Here, surrounded by the imposing views of the adjacent Castello di Poggio alle Mura, you can taste local sheep’s cheese and classic Tuscan prosciutto, all paired with their delicious estate wines (which range from San Angelo Pino Grigio to big wines like their Brunelli di Montalcino, BelnerO, SummuS ed ExcelsuS (all of which are available for purchase).
But aside from simply tasting the wine, I’d highly recommend staying at Il Borgo, their on-site hotel. Each of the rooms + suites is distinctly designed and original, embellished + decorated by hand, with premium fabrics + exclusive accessories (the entire premises have been furnished + decorated by Federico Forquet, one of the most renowned architects in all of Italy. It was seriously the perfect place to escape to on my own. I sat in my idyllic room that overlooked vineyards, drank some wine and enjoyed the views while I did some writing until the sun went down.
Once night fell, I walked over to La Sala dei Grappoli for an elegant Tuscan dinner (because dining solo is totally the time to go for a romantic candlelit meal in castle in Italy, right!?) I completely indulged in course after course of seasonal menu items, all paired with outstanding Banfi wines (and lots of bread, obviously).
My time at Castello Banfi was one of the most unforgettable nights of my life and I can't recommend it enough if you're looking for a quintessential Tuscan experience.
In the heart of the Chianti Classico region (just between Florence and Siena) is Fonte de’ Medici, which belongs to the Antinori Family--one of the most prestigious families in Italian wine-making. This stunning property dates back to 1400 and offers the beauty of the Chianti countryside, along with wealth of its food and wine.
Immediately upon arrival, I went straight to the Antinori Nel Chianti Classico cellars for a tour and tasting (I loved the 2011 Badia A Passignano). The property was stunning, and it was so fun to see a Chianti Classico facility since it’s such a prominent type of wine.
In case you were wondering, a Chianti Classico is predominantly made up of Sangiovese (although the exact percentage seems to be up for debate… I’ve heard it must be at least 75% and also 85%, but even David, the wine aficionado from Milan who attended our Friendsgiving over the weekend wasn’t sure!) Regardless of the exact percentage, they are premium Chanti wines that tend to be medium-bodied and are always labeled with an iconic black rooster seal. Why a black rooster you ask?
I’m told that according to legend, Florence and Siena long feuded over rights to the Chianti Classico region and decided to finally end it around 1200 with a competition. So the plan was to let horsemen depart from each city at the crow of their respective rooster. Wherever they met would determine the boundary line of how the region would be divided between the two. In Siena, they used a well-fed white rooster. In Florence however, they used a hungry black rooster. The reason? The morning of the race, the white Sienan rooster dutifully crowed at sunrise like he was supposed to, but the hungry black rooster in Florence begun to crow long before (thus giving them a significant head start and in turn, a larger portion of the region).
After drinking some delicious wine + learning tons about the history of the property, we headed back up to the hotel portion for dinner in the Trattoria (which offers incredible Tuscan cuisine and sweeping views). I loved chatting with my new friend Irene (the hotel manager) and learning more about the region and local culture while indulging in my delicious meal.
As if the food and wine, beautiful views and incredible hospitality wasn’t enough, they also offer activities you can participate in (cooking class, anyone?) Long story short, Fonte de’ Medici is a quintessential Tuscan oasis that will leave you relaxed, well-fed and immersed in the rich Italian culture.
Maybe it’s because I was alone and had space to be reflective, or maybe it's because I was in the countryside rather than the city-- but there was something about my time in Tuscany that impacted me more than any other place that I visited. I'm confident I'll look back years from now and hold great fondness for "that time I drove to the Italian countryside all by myself."
I can’t recommend these properties (or Tuscany in general) enough. If you’re wanting a relaxing European holiday that includes incredible epicurean options and with dazzling views, Tuscany is everything you’re looking for and more.
Anything else you want to know about Tuscany? Let me know in the comments!