3 Days in Tuscany
Growing up, I always talked about living amongst rolling green hills, tending to my garden and baby ducklings, kneading bread, and sitting on a wooden porch swing while reading under the sunlight. In reality, I’m a thoroughly metropolitan girl who panics at the mere sight of ants — but as the explosion of the ‘cottagecore’ aesthetic mid-pandemic exemplified, I think many people relate to the dream of a blissful countryside existence.
There is no place on earth that better matches my idyllic imaginings than the Tuscany region in Italy. Covering an area of 23,000 square kilometers / 8,900 square miles, Tuscany is a picturesque stretch of vineyards, olive groves, thermal springs, and many, many cypress trees. The region includes Florence, the birthplace and heart of the Renaissance; the world-renowned Chianti wine region; and cities such as Pisa, Siena, and Lucca.
If you’re not interested in driving, the easiest way to get a taste of the Tuscan countryside is to use Florence as a home base and visit other cities on day trips as part of a tour group. Siena is another great option as many day trips depart from there to popular smaller towns such as San Gimignano, Pienza, and Montepulciano. There are daily buses and trains between Florence and major cities such as Siena and Pisa, which offers some flexibility to explore at your own pace. However, if you have the time, I’d strongly recommend making a road trip of your visit so you can take your time and visit more towns. The weather and fog can shift before your eyes, so staying overnight will increase your chances of seeing some truly magical scenes.
We knew that most tourist attractions would be closed for Christmas Eve and Christmas Day, so these days provided the perfect window to drive from Rome to Florence with a few nights in the countryside. We’d also read online that Tuscan weather in December was highly variable: depending on the year and exact location, it could rain or snow, the hills could be yellow or green, and the fog might burn away in the morning sunshine or hang in the air all day.
For the months and weeks ahead of our trip, it was forecasted to rain throughout our entire time in Tuscany. On the drive from Rome through the Umbrian region, we could barely see ahead of us because of all the fog. We manifested, we prayed, we squinted at the sky for hints of blue behind the gray clouds. Lo and behold, as we emerged from a tunnel crossing from Umbria to Tuscany, it was like we had entered a dreamscape: brilliant blue sky above, ethereal fog drifting across lush hills below. Tears were shed; we blinked and pinched ourselves, scarcely believing our eyes. Thus we began our road trip, absolutely euphoric and filled with gratitude.
Day 1: Montepulciano, Val d’Orcia, Montalcino (Rosewood Castiglion del Bosco), Siena
Our first stop was Montepulciano, a hilltop town known for its prestigious red wine made from Sangiovese grapes, well-preserved medieval and Renaissance architecture, and of course, panoramic views. There is limited parking outside of the city walls. From there, just keep trekking up. There is no shortage of little alleyways to viewpoints on the way up, but for breathtaking 360-degree views, head towards the Piazza Grande and climb up the clock tower of the Palazzo Comunale. If you’re in town for the holidays like we were, spend some time wandering around their Christmas market! Vendors were selling precious artisan goodies and holiday snacks.
If you want to grab a non-holiday-themed bite on your way down, we can’t recommend Palazzo Avignonedi Caffeteria enough. Three delicious pastries and a coffee cost only 8.30€. That’s like one New York latte! Their pistachio cream croissant had such a rich, nutty flavor, and they served one of the best tiramisus we tried on the whole trip.
By the time we made it back to our car, we realized we had spent two hours in a town for which we’d originally allotted thirty minutes (oops). Our original, ambitious route included stops in Pienza and Montalcino, but we were on a tight schedule. We had made a lunch reservation at Rosewood Castiglion del Bosco and we still wanted to arrive in Siena before dark. Keep in mind, the sun starts setting around 4:30pm in December. Since we were sufficiently blown away by Montepulciano, we decided to drive past Pienza and head directly to lunch.
Our new route still took us through the winding roads of the Val d’Orcia, the most beautiful part of Tuscany and a UNESCO World Heritage Site. When people think ‘Tuscany,’ the Val d’Orcia is most likely what they’re picturing. While some areas we drove past throughout the day were indeed yellowed for the winter, these gentle slopes were still green.
If the primary goal of your visit is photography, definitely research where particular shots were taken ahead of time. The Chapel Vitaleta is a popular stopping point. Some locations, like the famous curved road of cypress trees at the Agriturismo Baccoleno near Asciano, may look close by on a map but could take an hour-long detour to reach due to limited roads. At the same time, don’t stress! The entire Val d’Orcia region is gorgeous — we made lots of random stops along the main road for quintessential Tuscany shots.
The most challenging part of the drive was the mountainous road into the Rosewood Castiglion del Bosco, a beautiful resort near Montalcino. This hotel has some serious amenities. As a founding member of the Consorzio del Vino Brunello di Montalcino, they produce the famed Brunello di Montalcino in their winery. They also house the only private golf club in Italy, designed by Champion golfer Tom Weiskopf. We only caught a peek of the course on the way up, but it was a destination golfer’s dream. Guests can enjoy the Michelin-starred Ristorante Campo del Drago for dinner, but we opted for a light lunch at their casual trattoria, Osteria La Canonica.
Originally, this lunch stop was designed to be a break from driving for my dad. It ended up being very memorable! Their handmade pici pasta with ‘aglione’ sauce was fantastic and a must-order. The sauce looks simple, but the combination of tomato and Val di Chiana garlic was so refreshing. The wines we ordered here were some of our favorites from the whole trip. I picked a glass of white from San Gimignano, which was bright, fruity-citrusy, and crisp. However, besides my brilliant wine order, this lunch was not my finest ‘foodie’ moment: I was mistakenly given the kid’s menu, and proceeded to double-down on the mistake by ordering a kid’s pasta in the hopes that it would just be a smaller portion size. While my family enjoyed tasty pizzas and pasta, my pitiful pile of ravioli was bland and flavorless. This was a good excuse to steal from everyone else’s plates… but what a missed opportunity! We could have shared another dish from the regular menu. Anyhow, the experience ended up being an exercise in empathy for my younger self. While I regret being such a picky eater when I was little because I surely missed out on some great culinary experiences (not eating any fish in Japan?!), perhaps items on kids menus are simply worse. Restaurants, you are doing your young guests a disservice! Feed kids well!
After checking out the hotel’s mini, curated Christmas market, we headed back to the car for the last hour-long drive to Siena. The sky melted from a typical pastel golden hour into a spectacular pink sunset, washing the valleys with warm, rosy light. As we drove, the glow of sunset deepened into a violet gradient dotted with striking cypress silhouettes. If we could’ve stopped every five seconds, we would’ve. Instead, we contented ourselves with shaky videos from hastily-lowered car windows and many mental pictures.
When we made it to Siena, we clunkily navigated our car through cobblestone streets filled with people. For our one night in Siena, we stayed at the Grand Continental Hotel Siena. This hotel is centrally-located and offers large, comfortable accommodations (for Instagram girls, they also have a palatial guest lounge that’s ideal for a photoshoot).
My research beforehand told me that the best dinner in Siena was at La Taverna di San Giuseppe. They only take phone reservations, so we asked our hotel concierge to make the call on our behalf. Even after making the reservation, I hadn’t particularly anticipated this dinner, but wow. This ended up being one of my favorite spots of the trip.
From the start, we were reassured by the wall of Michelin Plates proudly featured at their door and the crowd that had eagerly assembled right at opening time. We started off strong with Castello di Brolio, the flagship wine of Ricasoli, Italy’s oldest winery. We enjoyed two unique appetizers (a pastry and quail x pancetta dish, both generously dusted with fresh black truffle), but the unparalleled star of the meal for me was their cocoa tagliatelle (!!!!!). I have been drooling over the memory of the cocoa linguine I had at Boston’s The Salty Pig for years, but its permanent disappearance from their seasonally-changing menus had me questioning if I had just imagined it. Finally, my tastebuds have relived its glory and confirmed what I’ve always known: society needs to normalize cocoa pasta. Overall, this meal was non-pretentious, reasonably-priced, and authentic — the cherry on top to a perfect first day in Tuscany.
Day 2 (Christmas Eve): San Gimignano, Castello di Leonina Relais, Il Borro
Given our miraculous fog experience the prior morning, we weren’t sure what the fog situation would be in Siena, and were slightly dismayed when we threw open our curtains to see… nothing but fog. Following our concierge’s recommendation for the best viewpoint in Siena, we optimistically set our maps to Prosperino Bistrot, a cafe by a panoramic viewpoint. Unfortunately, like everything else, our would-be view was shrouded in haze. We did get to see a Terra Mater statue by Andrea Roggi (read about this public art project here).
As we walked around, hints of blue started to break through the sky, so we decided to bide our time. We enjoyed a homemade breakfast at Caffè 19zero3, one of the few places open on Christmas Eve, also conveniently located right by the central square, Piazza del Campo. When we stepped out of the cozy cafe, however, we were startled to see that those elusive patches of blue had disappeared behind more fog. Had we missed our chance? Alas, our time in Siena was limited. Ever-determined and blindly hopeful, we clambered up the 400 steps of the Torre del Mangia and once again, couldn’t believe our luck. The sky was blue and the city’s layered buildings appeared to rise from the fog like in a fairyland. We could see the mist shifting and blowing with the breeze as new sections of the city unveiled themselves to us, like the whole sky was letting us in on the secret treasure that is Siena. Look here, look again.
Above the clouds, we chatted with another friendly tourist. As he was about head back down the stairs, he hesitated and looped back to gaze out from the ledge a moment longer. He said, “we get so caught up in taking pictures that we don’t actually look at the scene — and it’s worth just looking at.” Words to live by! We stayed up there, just walking around to see every side of the city until the next round of tourists came up.
Descending from the bell tower felt like waking up from a daydream. When we’d started climbing, a layer of mist hung over the quiet city. Now, the fog had mostly evaporated, bringing everything into sharp focus. The city and its tourists had woken up. Little kids, bundled up in puffy coats, gleefully skipped around the sunlit plaza. Everyone was merry — even the dogs who chased each other around, making new friends.
The Piazza del Campo is one of Europe’s greatest medieval squares, and it still inspires today. My dad told us about Niall Ferguson’s The Square and the Tower, a book which uses the visual of Siena’s square to talk about the historical struggle for power between hierarchies (represented by the bell tower) and social networks (represented by the Palazzo Pubblico, once Siena’s town hall). Also noteworthy in Siena are its cathedral (Duomo di Siena) and the Libreria Piccolomini (a small library with frescoes by Pinturicchio). If you happen to visit on July 2nd or August 16th, you can watch their annual horse races, Palio di Siena.
We said our goodbyes to Siena and headed out on our detour to San Gimignano, another popular Tuscan hilltown known as ‘Medieval Manhattan’ for its 14 remaining medieval towers. Siena and San Gimignano are both UNESCO World Heritage Sites due to their well-preserved historic city centers. Everything was closed since it was Christmas Eve, so we wandered around to the edge of town for more panoramic views of the valleys below and went on our way.
Some context: the very first place we booked for this whole trip was Il Borro. I wanted to make sure we had plenty to do on Christmas, when most tourist attractions and restaurants would be closed. Il Borro, a Ferragamo family estate about an hour outside of Florence, was a perfect choice. The hotel is surrounded by 1,100 hectares of organic land and even has a medieval village of its own with artisan shops and a church. Guests can enjoy horseback riding, golf, tennis, wine tasting, truffle hunting, cooking and mixology classes, art classes, and more. It was definitely the priciest stay of the trip, but as their website claims, it is “a place like no other.”
But let’s back up. We had to refill our car with diesel (not regular gasoline!), so my dad — ever the thoughtful planner — found a gas station between San Gimignano and Il Borro that was 1) open on Christmas and 2) close to one of the photo spots we’d missed the day before: Castello di Leonina Relais, a hotel perched on a hill. We again faced seemingly hopeless levels of fog. We drove at a snail’s pace and watched for the occasional headlights of cars passing by.
When we parked at the top of the hill, though, we were overwhelmed by yet another unreal scene. On one side, odd hills that looked like giant boulders overgrown with moss stood by a lake. On the other, cypresses beckoned towards verdant hills that cascaded upon one another. The fog, seeming to cooperate with our photographic needs, gracefully rolled past, letting the hills peek out overhead. Golden hour cast the whole place aglow.
I was absolutely giddy with our good luck. Reader, I couldn’t help but frolic. There was no one around but us, so I frolicked and leapt with joy and counted my blessings.
Our drive to Il Borro was uneventful. We settled into our family suite and headed to our Christmas Eve dinner at Osteria del Borro. The menu was on the unadventurous side, but we enjoyed the impeccable service, the perfectly-prepared beef fillet entree, and at least five rounds of different homemade breads (“you’re in Italy… there’s going to be bread!”).
Day 3 (Christmas Day): Il Borro
Our last full day in the Tuscan countryside was cloudy (God’s sign to stay put instead of driving back out into the countryside). We slept in, enjoyed a late buffet breakfast, explored their medieval village — including super elaborate mechanical puppet theaters of the Nativity story, Il Borro’s own community, and Pinocchio — and finally played Bananagrams.
Megan and I went horseback riding in the afternoon, which was so exciting. We attended a riding summer camp way back in middle school when we spent our summers in California, but it had been ages since either of us had ridden. Our guide showed us around the grounds and we chatted about school and the horse training/competition industry in the US versus at Il Borro and similar European estates (spoiler alert: the US’s approach is more lucrative and less humane). It’s always interesting to talk to someone who’s an expert in a subject you know nothing about. The world is so big and everyone is doing different things! There is always more to learn!
We returned from our ride and promptly fell asleep. It was such a satisfying nap that I only woke up in time for dinner. This time, we headed to their casual Tuscan Bistro, which was actually more to our tastes than their fine dining restaurant. The secret standout of the night was their homemade bread and olive oil. At first glance — and even at first taste — the bread seemed stale and flavorless. Yet in combination with their fresh, slightly bitter olive oil, the bread became absurdly addictive. One mouthful and I felt as though I’d been transported into the body of a medieval farmer, sitting on a tree stump and chewing a baguette after a long day’s work. Think of the scene of Farmer Hoggett sharing bread with Babe after successfully herding sheep in the cinematic masterpiece, Babe (1995). That is precisely where the Tuscan Bistro’s bread will take you.
Our road trip was a series of serendipities. We placed ourselves at the mercy of Tuscany’s weather and it responded by sending us one breathtaking moment after another. With experiences like these, how could one not believe in a gift economy? In Braiding Sweetgrass, Robin Wall Kimmerer writes, “Gratitude creates a sense of abundance, the knowing that you have what you need. In that climate of sufficiency, our hunger for more abates and we take only what we need, in respect for the generosity of the giver. If our first response is gratitude, then our second is reciprocity: to give a gift in return. […] To name the world as gift is to feel one’s membership in the web of reciprocity. It makes you happy—and it makes you accountable.”
As my family and friends know, I’ve always considered myself weather-lucky. When I travel, I deem forecasts irrelevant. I ‘manifest’ and more often than not, my manifestations come true. The predicted rainy day never arrives. While I may joke about my sheer willpower turning the weather, I am surprised and grateful every time it happens. It does indeed feel like a gift from the world to me. What can I give in return? Perhaps that is the question of our entire lives. The chance any of us would be brought into existence is infinitesimal. How can we repay the gift of getting the chance to be alive?
The simplest answer is to leave things better than we found them so that the world can keep giving gifts to future generations. However, ‘better’ has become harder to determine. Technology is often framed as a gift of our own creation, and most people likely wouldn’t trade our technological progress to restore a more intimate relationship with nature.
I don’t have an answer to these questions, and this discussion is now totally out of the scope of this supposed Tuscany travel guide, but I would suggest that we all start by simply paying enough attention to see the gifts we are bestowed on a daily basis. It’s easy to see luck when we travel and face unusual circumstances because we expect some things to go wrong. The trick is to see it everywhere else too — because in fact, every good thing is a gift.
