Tuscany was everything I imagined. Rolling hills, draped in vineyards and olive groves interwoven with cypress-lined lanes that lead to secluded estates offering breathtaking views at every turn. I wander through enchanting villages, marvel at exquisite art and architecture, and indulge in the region’s extraordinary food and wine. Along the way, I even have the privilege of exploring three UNESCO World Heritage sites: the idyllic Val d’Orcia, Pienza, and the historic city of Siena.
Despite being renowned for its stunning landscapes and timeless charm, this central Italian region offers more than its postcard-perfect scenery. The more I explored, the more evident it became that the soul of Tuscany lies in its wine.
My trip wasn’t just about savouring a glass of Chianti, it was also about diving into the stories behind the wine and discovering the essence of Tuscan life through its rich winemaking traditions. I discovered that Tuscany’s wineries are more than places to taste wine, they’re living pieces of history – where art, architecture, and tradition come together in a uniquely Italian way.
The Antinori nel Chianti Classico complex is more than just a winery; it’s a masterpiece of contemporary design and a testament to the combination of tradition and innovation. Completed in October 2016 after seven years of meticulous planning and construction under the direction of architect Marco Casamonti, this striking structure is a sight to behold. Hidden within the hillside, the winery seems to emerge organically from the earth, its terracotta hues and use of natural materials blend seamlessly into the surrounding Tuscan landscape. This mix of tradition and innovation is especially evident in the cellar, where rows of oak barrels are stored in a naturally climate-controlled environment – a truly striking sight.
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Equally interesting is the on-site museum, which delves into the Antinori family’s winemaking legacy, dating back to 1385. Together, the winery and museum offer an immersive journey that celebrates both the artistry and the beauty of its architectural ingenuity.
After my tour, I enjoyed lunch at Rinuccio 1180, the rooftop restaurant named in honour of the family’s ancestor, Rinuccio degli Antinori. With breathtaking views of the Chianti Classico countryside, it’s the perfect place to soak in the full beauty of the vineyard. The menu featured simple, seasonal dishes made with locally sourced ingredients, offering an authentic taste.
Beneath the streets of Montepulciano, you will find Cantina De’ Ricci, a historic and unique landmark known as the ‘Cathedral Winery’. Its unassuming entrance leads to a labyrinth of ancient stone cellars, vaulted ceilings, and Gothic-inspired arches. Walking through this stunning space feels like a journey through time, with a guided tour culminating in a wine tasting. For lovers of history and architecture, this spot is unmissable.
La Pia Percussina, a family-run biological farm in San Casciano, is a slice of Tuscan history. When the owners purchased the property, they thought they were simply buying a house, only to later discover its deep-rooted connection to the region. Nestled in the Chianti hills, this small estate blends tradition with innovation, practising sustainable farming long before it became fashionable. Their approach preserves the land’s biodiversity while crafting wines that pay homage to their heritage.
Driving into Volpaia feels like entering a medieval postcard. This tiny hamlet, with its stone towers and cobblestone streets, is home to Castello di Volpaia — a winery where history and winemaking intertwine. Wine flows through underground tunnels connecting cellars hidden behind centuries-old walls, making the entire village part of the winemaking process. It’s a picturesque slice of Tuscany, producing some of the region’s finest wines.
Nittardi is where creativity and winemaking collide. Perched between Castellina and Panzano, the journey takes you through a dusty, winding road through the Chianti hills, but the destination is worth it. Art takes centre stage here, with sculptures scattered throughout the estate and vibrant artwork adorning the winery walls. Each year, a renowned artist designs the label and wrapping for their Casanuova di Nittardi Vigna Doghessa wine, a tradition that has included the likes of Yoko Ono and Günter Grass.
Housed in a former monastery, Tempio del Brunello offers an interactive dive into the story of Brunello wine. From its origins in the 18th century to today’s meticulous winemaking process, the museum blends tradition and modernity seamlessly. The experience ends in a stunning tasting room that’s perfect for sampling the wines on offer.
- Best time to visit: September and October are ideal for the grape harvest.
- Getting around: Rent a car to explore Tuscany’s rural wine regions, but plan for a designated driver if you’re sampling wines.
- Book ahead: Popular wineries often require reservations, especially during peak seasons.
- Join a tour: Joining a tour can provide insider knowledge and unique access to the region’s wine traditions.
Wine aside, Tuscany is a treasure trove of art, history and culture, where medieval towns and landmarks transport you back in time. These towns – each with a unique charm – capture the essence of Tuscany.
One of the most captivating places I visited was Badia a Passignano, a Vallombrosian ancient monastery in the rolling hills of Chianti. It’s hard to believe that this serene haven was founded back in 395 A.D., and even more remarkable that it’s still home to a community of monks today. The monks farm and produce goods for their small shop and carry on traditions that have sustained them for centuries. Inside, the monastery’s interior is filled with historical artefacts. I was awestruck by the incredible Renaissance artwork, including pieces by Domenico Ghirlandaio.
Montepulciano is a town where history is woven into its very fabric. I started my visit in Piazza Grande, the town’s beating heart and a vibrant gathering place. Surrounded by elegant Renaissance architecture, the square is anchored by the imposing Palazzo Comunale, a 14th-century masterpiece that stands as a testament to Montepulciano’s storied past. Nearby, is the charming Il Pozzo dei Grifi e dei Leoni, a Renaissance-era well adorned with intricate carvings.
Just a short walk away, the Duomo of Santa Maria Assunta stands proudly at the highest point of the town, its unassuming façade hiding treasures within. As I walked along the cobblestone streets, my guide explained how Montepulciano was once a formidable fortress. I was especially captivated by the panoramic view from Vicolo della Mura, which offered a sweeping vista of the Sienese Valdichiana below. The patchwork of vineyards and olive groves stretching as far as the eye could see felt like a painting come to life.
And a fun fact for movie buffs… Montepulciano played a starring role in New Moon, the second Twilight movie – and I could see why. The town is impossibly cinematic, with its hidden churches, sunlit piazzas, and stunning countryside views at every turn.
Next, I headed to Pienza, famed for its Pecorino cheese. Walking through the Prato Gate, a stone archway, I was immediately transported back in time, with faint carvings on the stone that speak of the town's ancient past. At the heart of Pienza is Piazza Pio II, its main square surrounded by architectural masterpieces like the Palazzo Piccolomini and the Cathedral of Santa Maria Assunta.
As I strolled down Corso Rossellino, Pienza’s main street, I found myself drawn to the artisan shops that line the way, selling everything from colourful textiles to handcrafted ceramics. One of the highlights of my visit was stepping out onto one of Pienza’s panoramic terraces. The view of the Val d’Orcia below was nothing short of spectacular, a landscape of rolling hills, cypress-lined roads, vineyards, and fields of sunflowers. Pienza’s tranquil beauty and stunning views make it the perfect place to linger and take in the surroundings.
San Quirico d’Orcia is a quaint village that’s often overlooked in favour of its more famous neighbours, but this hidden gem quickly won me over with its narrow, stone-paved streets, charming piazza and quiet charm. The crown jewel of San Quirico d’Orcia is the Horti Leonini, a 16th-century garden designed by Diomede Leoni. Walking into the green space felt like stepping into a secret oasis. Tucked behind unassuming walls, the symmetrical paths, neatly trimmed hedges, and towering cypress trees create a perfect harmony, and the views of the surrounding countryside are simply breathtaking.
My final stop was Siena, a medieval gem in the heart of the region. I began at the Civic Museum of Siena, located inside the Palazzo Pubblico – Siena's magnificent city hall – with its towering Mangia Tower. The frescoes are what truly captivated me, starting with Ambrogio Lorenzetti’s Allegory of Good and Bad Government. I’d heard about it before, but seeing it in person was an entirely different experience. The detail, the symbolism, and its vivid portrayal of how governance shapes society are not just art; it’s a profound statement that still holds relevance.
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From there, my guide, a passionate storyteller brimming with knowledge, led us through Siena’s cobblestone streets. Our first stop was Piazza del Campo, the city’s iconic shell-shaped square, famous for the annual Palio horse race. As I wandered through Siena’s winding cobblestone streets, I couldn’t resist stopping by some of the city’s famed delicatessens. This led me to Il Magnifico, a beloved family-owned bakery that has been making artisanal sweets since 1952. Inside, Lorenzo Rossi, the current owner, introduced me to Panforte, a centuries-old pastry created for religious festivals and celebrations. This rich fruitcake, with its blend of honey, dried fruit, spices, and a delicate wafer base, is the most famous dessert in Siena. I then headed to La Bottega Senese, a rustic deli tucked along Via di Città. The shelves were lined with regional specialities, jars of truffle honey, and an array of cured meats. I sampled their house-made finocchiona, a fennel-spiced salami that was rich and aromatic, alongside a slice of salami infused with wild fennel.
By the time I arrived at the Cathedral of Siena, the anticipation was palpable. Often referred to as a jewel of European art, the cathedral didn’t disappoint. Its striking black-and-white striped marble facade is striking, but stepping inside felt like entering a different world. The guide's narration brought the cathedral to life, weaving stories of its construction and the master artists who contributed to its grandeur. Michelangelo, Donatello, and Pinturicchio all left their mark here, but the pièce de résistance was undoubtedly the marble inlay floor. Unveiled only for a limited time each year, the intricate designs felt like a symphony in stone, depicting Biblical stories and allegories with astonishing detail.
I may have come for the wine, but Tuscany offered me so much more – I'll be back.
For more information, visit the official tourism website Visit Tuscany
