If ever there was a destination fit for a postcard it would be Tuscany. It took me 15 years of traveling to Italy with a decent amount of regularity before I finally visited this much-adored region defined by its rolling hills, cypress tree-lined roads and delicious wine, cheese and pretty much everything in between. And while it may all seem cliché, there’s a reason that Tuscany is the stuff that Italian dreams are made of. My first time in Tuscany was part of a bigger first, my son’s first trip to Italy. And without realizing it, our time spent in Tuscany would also overlap with the Easter holiday, making it all the more memorable while providing a perfect little pause between visits to Venice and Rome. Here’s how we spent 3 lovely days in Tuscany.
Day 1
Leaving behind rainy Venice, we lugged our luggage to the main transit hub Piazzale Roma to pick up our rental car. As we set out for our next home away from home in the Tuscan countryside, we first made a detour to Cittadella just north of Padua. This walled city dates back to the 13th century when it was a military outpost and holds the superlative as the only city in Europe to have a fully elliptical, walkable parapet encircling the town. We figured we might not have a car in this part of Italy again so didn’t want to miss the opportunity to visit. Our visit was short since the road was calling us, or at least the grumblings of our stomach that required an obligatory stop at an Autogrill to refuel. These are one of the best parts of an Italian road trip, and I still relish my son’s wide-eyed excitement during his first encounter with the elevated roadside rest stop.
By late afternoon we had arrived at the Fonte Bertusi and were warmly greeted by our hosts Antonio, Manuela and their 5 cats with names like Mario, Bruschetta and Sushi. Nestled in the fertile Val d’Orcia less than 10 minutes from Pienza with easy access to other towns in the area, it provided the perfect place to call home during our time in Tuscany. Manuela showed us to our appropriately named apartment Il Cipresso, which featured a kitchen, bathroom, bedroom and private patio. The former country machine storage room offered just the right amount of space and oozed farmhouse charm punctuated by the artistic flair of the family’s paintings.
We were quick to drop off our bags and explore the beautiful property, the first signs of spring peeking out among the wild and rustic grounds. There were cypress and olive trees and other plants and creative curiosities strewn about, along with a relaxing pool for warmer weather, a library featuring Andrea’s pop art paintings, a beautiful breakfast room with Manuela’s sewing treasures (both available for sale) and views as far as the eye could see… The only thing that was not expected was the moody sky that hung above us (a theme that would continue throughout our stay).
Afterwards we headed to Pienza for dinner. It was the darkest evening of our trip leading up to the daylight savings time change the following day, but that didn’t deter us from soaking in this beautiful Renaissance town and birthplace of Pope Pius II. It was love at first sight as we wandered through its charming streets adorned with an abundance of potted plants and flowers. Shortly before opening time, a small crowd gathered outside of Sette Di Vino (Piazza di Spagna, 1), which is situated on a lovely piazza with a Romeo and Juliet-esque balcony and wishing well in its center. We heard that the owner was a no-nonsense man, and the sign outside the restaurant solidified this. “No pasta, no pizza, no Coca-Cola, no cappuccino, no internet,” it read, which basically translated to no frills and no touristy B.S., a sure indication that this was going to be a memorable evening.
At 7:30pm on the dot the doors flew open and we were led to an intimate dining room upstairs that felt as if we had entered someone’s home. A handwritten menu listed an assortment of limited offerings, simplified even further by the owner who went from table to table to make his personal recommendations. Not long after placing our order, a procession of small plates began to appear at our table – grilled pecorino, bruschetta with tomatoes, chickpeas with rosemary, a radicchio salad, grilled eggplant and our first encounter with ribollita soup, which we washed down with a pitcher of red wine. The entire experience was so much fun that we didn’t want it to end, but we knew another reservation was right after us as noted by a little card on the table. Yet the owner reassured us that we didn’t have to rush as he served us a plate of cantucci with Vin Santo dessert wine to cap off our meal.
Originally we had planned to go to Montepulciano the next morning for Easter mass, but we instead decided to stay in Pienza to attend the Easter Vigil at the Duomo di Santa Maria Assunta. It made for an incredibly long and late night, first waiting outside the cathedral on the piazza as temperatures continued to drop, followed by a nearly 3-hour long mass full of ceremony and tradition (which my son slept through comfortably on my lap), but made for an unforgettable celebration nonetheless.
Day 2
After a much-needed sleep, we started the day with the most incredible breakfast prepared by Manuela. Her bountiful spread was nothing short of impressive, consisting of cereals, yogurts, cakes, cookies, pastries, breads with various spreads, marinated vegetables, meats, cheeses, juices and made to order coffee. We filled our plates with a mountain of sweet and savory delights and settled in at one of the tables overlooking the surrounding valley.
It was Easter and our plan for the day was to visit a handful of towns and sites throughout the Val d’Orcia. We thought it might be on the quieter side because of the holiday, but it seems like other families had the same idea as us. Our first stop was Bagno Vignoni, a hilltop village known for its natural hot springs. This historic spa town dates back to Roman times when the 125-degree Fahrenheit waters in the central pool were revered for their therapeutic properties. While people are no longer able to enter the pool, you can visit one of the modern spa complexes or touch the tepid waters on the other side of town at the Parco dei Mulini thermal pools set among the ruins of a former mill building. As we made our way through town we also stopped at Erboristeria Erba Mistica (Piazza del Moretto, 39) to purchase some handmade soaps and ceramic dishes as gifts.
Our next stop was the charming medieval town of San Quirico d’Orcia. We took advantage of a brief sunny spot in the afternoon to enjoy a spritz at Bar Centrale (Piazza della Libertà, 6) on the piazza with a lovely view of the Piazza e Chiesa della Madonna before exploring the town’s maze-like Horto Leonini community gardens.
En route back to the Fonte Bertusi, we made one more stop along SP142 at a sign labeled “Cartolina della Toscana”, which was not only a scenic viewpoint but also a marker for the start of a short hike to the postcard-perfect Cappella Vitela. After a 20-minute hike down a dirt road and then up a rather steep incline, we reached this small, secluded chapel sitting atop the grassy hill. While you can take in the views from this high point, you are not allowed to sit on the grass in front of it (those who do will be politely asked to leave by a discerning security guard). After some time, we made our way down the hill and back to our car, and couldn’t help but notice how smokey and smoggy the air around us looked, which we learned from Manuela was actually the result of a sandstorm in the Sahara.
Later that evening we headed to Montepulicano for Easter dinner. Widely known for its namesake red wines, this famed Tuscan destination is the perfect embodiment of the region’s medieval past. Entering through the Porta al Prato of the fortified hill town, we were met by crisp air mingling with the smell of wood-smoked meat. The town was buzzing, as we joined the flow of people ascending the main Corso, stopping in little shops along the way and then again on the hour to watch Pulcinella ring the bell from his post atop the clock tower.
Soon after we arrived at Trattoria di Cagnano (Via dell’Opio Nel Corso, 30) in eager anticipation of our holiday feast. We were seated at a corner table and watched the restaurant fill up quickly with other families presumedly looking to do the same. It was a quintessentially Tuscan spot, with wooden beams and details throughout its warm interior and a menu of hearty grilled meats and traditional pastas. We started with a large pecorino cheese board featuring 6 different types of the region’s trademark cheese along with a variety of accompaniments. By the time our main courses arrived we were already much too full but could not resist stuffing ourselves with yet another bowl of delicious ribollita, picci pasta with ragu and an assortment of grilled meats. Despite feeling overly full, we somehow still found room for coffee and tiramisu for dessert. In much need of an after dinner walk, we left the restaurant and continued up through the town to its Fortezza at the top before heading home. My only regret was that we didn’t get to spend more time exploring Montepulciano during daytime hours, leaving us with a reason to return someday.
Day 3
Easter Monday (Pasquata) is typically a day where Italian families head out to the countryside for a picnic or other outdoor adventures, but the weather had different plans. It was rainy, but more than just springtime showers, rather it was pouring and frigidly cold, leaving us chilled to the bone as we wandered through the walled hill town of Montalcino. Famous for its Brunello wine, we parked at the south side of town and wandered through its medieval streets dotted with shops, restaurants and of course wine bars as we made our way to the 14th century fortress at its highpoint. The courtyard of the Fortezza is free to enter and gives you a sense of its once defensive role, with the option to climb its ramparts for a fee. Most other places were closed for the holiday, sans a small market on the arcaded loggia near Piazza del Popolo where we purchased candies and locally-produced jams and sat under its protective covering to concoct a gameplan for the rest of the day. Initially we had hoped to hike along some of the nearby vineyards, but that was now out of the question. We took a quick coffee break at Bar Prato (Piazza Camillo Benso Conte di Cavour) before braving the harsh conditions on the way back to our car.
We had already purchased tickets to the Abbazia di San Galgano about an hour and a half drive away, and since it would allow us to spend a good amount of time in the car, we decided to carry on with our plans. All that remains of this former 13th century monastery is a shell of its former glory, a roofless abbey in the middle of an open field. After walking down the cypress-lined drive, we first stopped at the little café/restaurant adjacent to the abbey to warm up with another snack before heading to the abbey. The site was evocative. Gothic walls towered over us, arched windows once filled with sparkling stained glass were now empty, the entire site exposed to the elements. It was well worth the effort to get to San Galgano, which we were able to explore with few other visitors. The silver lining to the day’s wet and cloudy weather.
For our last evening in Tuscany we returned to Pienza where, for the first time all day, the sun finally made an appearance. Sitting on the edge of the wall of the panoramic viewpoint along Via Gozzante on the western part of town, the entire countryside was bathed in the most glorious golden light. The rain had washed away the clouds and smog and the air was now clear and fresh as the sun made its final descent on the distant horizon.
Afterwards we headed to Ristorante del Falco (Piazza Dante Alighieri, 3) located just outside of the town walls where we had dinner reservations. While the restaurant’s regular menu looked amazing, we were treated to a special Pasquata menu, from which we ordered cacio e peppe gnocchi and ravioli filled with cheese and spinach and topped with walnuts. I was also lucky to get the last available bowl of ribollita of the day, along with an insalata mista to share. Our meal was nothing short of delicious, which we capped off with another Vin Santo and cantucci as well as a light-as-a-feather pistachio cream profiterole for dessert. It was the best possible ending to our time in Tuscany, back in what had become our favorite town where we enjoyed not one but two of our favorite meals.
One final note…
As we loaded our bags into the rental car and said our goodbyes to Andrea, Manuela and the Fonte Bertusi (and the cats), we had no idea that the region would send us off with one final gift. For the first time in 3 days, bright blue skies met rolling green hills at a seamless horizon interrupted only by the pointy tips of cypress trees, as we made our way down the winding roads towards Rome. We pulled over so many times to take “just one more photo” in hopes of capturing this moment in time exactly as it was, casting doubt if we would ever make it to our next stop, Civita di Banaregio, a charming hilltop village only accessible by pedestrian bridge, let alone Rome before the end of the day. This was the Tuscany that, while overrepresented on every postcard, calendar or movie set in the region, I had long hoped to see.
ON THE MAP
Boarding Pass 