Tucked into the rolling hills of central Tuscany, Siena is one of Italy’s most enchanting medieval cities. With its fan-shaped piazza, Gothic architecture, time-honored traditions, and romantic alleyways, Siena feels like a journey back to the Middle Ages—especially during the Palio, its legendary horse race. Whether you're a lover of history, art, or Tuscan cuisine, Siena promises an experience soaked in culture and soul.
One of Europe’s most beautiful medieval squares, known for its unique shell shape and red-brick pavement. It's the heart of city life and the site of Il Palio, the intense horse race held twice a year.
A stunning black-and-white marble cathedral blending Romanesque and Gothic styles. Highlights include the Piccolomini Library, exquisite frescoes, intricate floors, and sculptures by Michelangelo, Donatello, and Bernini.
Located beside the cathedral, this museum offers priceless artworks, including Duccio’s Maestà, and access to the Facciatone, a panoramic viewpoint over Siena.
Climb this 14th-century tower for one of the best panoramic views in Tuscany—if you can conquer its 400 steps!
An austere Gothic church home to relics of St. Catherine of Siena, including her mummified head.
Pici Cacio e Pepe – Thick hand-rolled pasta with peppery cheese sauce.
Ribollita – Hearty Tuscan bread and vegetable soup.
Panforte di Siena – A dense, spiced fruitcake dating back to the 13th century.
Ricciarelli – Soft almond cookies, ideal with vin santo wine.
📍 Best dining experiences can be found in Via di Città or Via del Porrione, home to charming trattorias and wine bars.
Mercato di Piazza del Mercato (Fridays) – Local produce, meats, and handmade goods.
Via Banchi di Sopra – Fashion boutiques, artisan shops, and souvenirs.
Nannini Café – Pick up authentic panforte, ricciarelli, and gourmet coffee.
Hotel Athena – 4-star comfort within the city walls and sweeping countryside views.
Palazzo Ravizza – Historic charm with a private garden overlooking the hills.
La Terrazza sul Campo – A boutique B&B with rooms overlooking Piazza del Campo.
Spring (April–June) and Autumn (September–October) offer perfect weather and fewer crowds.
July 2 and August 16 – For the Palio di Siena, book far in advance to witness this electrifying tradition.
Winter – Quieter and more atmospheric, with festive lights in December.
By Train: About 1.5–2 hours from Florence and 3 hours from Rome.
By Car: Driving is scenic but cars are restricted within the old city; park outside the walls.
On Foot: Siena is best explored by walking—its compact historic center is pedestrian-friendly.
Palio di Siena – A thrilling bareback horse race between the city's 17 contrade (districts), full of pageantry, parades, and fierce pride.
Siena Jazz Festival (July) – International performers take over city venues with soulful sounds.
Settimana Musicale Senese (July) – A classical music festival celebrating Sienese composers.
Chianti Wine Region – Just a 30-minute drive for vineyard visits and tastings.
San Gimignano – A hilltop town famous for medieval towers and saffron.
Montepulciano – For Vino Nobile wines and Renaissance architecture.