Siena feels like stepping into a postcard that somehow smells like truffles and sun-warmed cobblestone. Here, days unfold with the quiet reverence of tradition — a city forever in touch with its medieval roots yet alive with Tuscan warmth, food, and flair. For those who revel in a slower pace, Siena’s maze of narrow streets, storied landmarks, and al fresco dining is nothing short of poetic. Whether you’re sipping an aperitivo in Piazza del Campo or losing yourself in the frescoed halls of the Duomo, Siena has a knack for turning everyday moments into something cinematic. Let’s dive into the city’s secrets, where history and elegance meet over a glass of Brunello.

Storied Landmarks

Piazza del Campo | There’s no mistaking the heart of Siena — Piazza del Campo, a fan-shaped square unlike any other. Home to the world-famous Palio horse race and encircled by medieval palazzi, this piazza draws both locals and travelers to its open center. Spend an afternoon sipping espresso or aperitivo and watch the city’s heartbeat in motion.

Siena Cathedral (Duomo di Siena) | A masterpiece of Italian Gothic design, the Siena Cathedral wows with intricate black-and-white marble and jaw-dropping mosaics. Step inside to explore the Piccolomini Library frescoes and the gilded pulpit — each detail a testament to Siena’s rich artistic legacy. Climb the Facciatone for stunning views over Siena’s rooftops.

Palio di Siena | Twice a year, the Palio brings a wave of medieval pageantry and fierce competition to the city’s streets. To get a feel for the race’s intensity, take a guided tour that dives into the history of Siena’s 17 contrade, or neighborhoods, which compete in this centuries-old tradition. Visit a contrada museum to see the Palio banners and feel the city’s pulse beyond the race.

Pinacoteca Nazionale | Housing works by some of Siena’s most celebrated artists, this national gallery is a must for those passionate about Italian art. Wander through rooms filled with Gothic and early Renaissance paintings, with standout pieces by the likes of Duccio and Simone Martini. It’s an intimate, enlightening experience for art aficionados.

Tuscan Flavors

Osteria Le Logge | Set in a former 17th-century pharmacy, Osteria Le Logge brings elegance to traditional Tuscan fare. Expect creative twists on local ingredients, with dishes that might feature homemade pici pasta or delicate rabbit. Cozy up with a glass from their impeccable wine list and dine among locals who know they’ve found one of Siena’s best-kept secrets.

Antica Osteria da Divo | In the shadow of the Duomo, this refined yet rustic spot invites you to dine in ancient Etruscan tombs. Yes, you read that right. The menu spotlights hearty Tuscan classics: truffle-laden pasta, rich wild boar, and perfectly seared Florentine steak. It’s intimate, unforgettable, and ideal for savoring Siena’s boldest flavors.

Castello di Ama Winery | Just a short drive from Siena, Castello di Ama offers a wine-tasting experience that blends world-class Chianti with contemporary art installations across its historic estate. Wander the lush vineyards, enjoy guided tastings of their finest reds, and tour the cellar — all with panoramic views of Tuscany’s rolling hills. An afternoon here feels like a taste of the Italian good life.

La Canonica Cooking School | For those eager to roll up their sleeves, La Canonica at Castiglion del Bosco provides an immersive culinary experience. Under the guidance of expert chefs, you’ll learn to prepare traditional Tuscan dishes using fresh, local ingredients. After cooking, savor your creations paired with exceptional wines, offering a delicious connection to the region’s rich gastronomic heritage.

Beneath the Tuscan Sun

Val d’Orcia | For those craving a taste of the Tuscan countryside, head to Val d’Orcia, a UNESCO-listed landscape renowned for its rolling hills, cypress trees, and picturesque vineyards. Rent a bike or hike through the scenic trails, stopping at charming villages like Pienza and Montalcino, where you can indulge in local cheeses and wines while soaking up the stunning surroundings.

Truffles & Brunello | Enjoy a delightful truffle hunt in the stunning Tuscan countryside, where you’ll learn about the art of foraging for these culinary treasures alongside skilled guides and trained dogs. Afterward, indulge in a special wine tasting featuring the renowned Brunello di Montalcino, savoring the bold flavors that this prestigious wine region has to offer. It's a feast for the senses that captures the essence of Tuscany.

Golf | Tee off at The Club at Castiglion del Bosco, Tuscany's only private golf club — reserved exclusively for Members and Resident Guests of Rosewood Castiglion del Bosco. This exceptional course offers breathtaking views of the surrounding landscape and an unparalleled golfing experience.

Nature Walks in Montepulciano | A short drive from Siena, the hill town of Montepulciano offers stunning landscapes and hiking trails that reveal the beauty of the Tuscan countryside. The walk to the nearby Val di Chiana provides panoramic views and the chance to spot local wildlife. The vineyards and olive groves create a picturesque backdrop for a day of exploration.

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