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Perched high atop a hill overlooking the Tuscan plains, Siena is a masterpiece of medieval architecture, with soaring churches and Gothic palaces, some dating back as much as 800 years. Built around Piazza del Campo and sprawling out like a web, the historic city center is broken into 17 districts, known in Italy as contrade. Within each district is a designated church and museum dedicated to the contrada’s history, along with winding lanes boasting tempting eateries and artisan boutiques. Today, the city is known for its intricate monuments, incredible art exhibits, world-famous horserace, and mouthwatering cuisine—together ensuring visitors a feast for the eyes, soul, and stomach.
Unlike in other cities in Italy, Siena’s contrade are not just neighborhoods, they serve as mini city-states that provide both a physical and symbolic hub for community, family, and life. Here, loyalty is so fierce that locals consider their contrada to be much more important than any connection to that of Italy or Siena. Each district is defined by a mascot, flag, colors, and borders, and the only neutral ground in the city is Piazza del Campo. This rivalry is never more strongly on display than in July and August, when the districts compete in the famous Palio horserace for the pride of being top contrada. If visiting Siena for the first time, these are the areas you need to know.
Piazza del Campo — Sitting in the center of Siena, Piazza del Campo is the heart of the city’s historic district. The medieval square is surrounded by elegant buildings, including the Gothic Pubblico Palace and its 285-foot (87-m) tower. The square is famous for its magnificent Gaia Fountain and annual celebrations, most notably the Palio horseraces which draw tens of thousands of viewers each year.
Aquila (Eagle) — To the southwest of del Campo lies Aquila, one of the city’s smaller districts yet home to one of it’s biggest attractions, the Siena Cathedral. Step inside the 13th-century structure to admire the majestic mosaics and beautiful baptistery. After paying a visit to the underground crypt, climb up to the panoramic terrace for a sweeping view over the city and surrounding Tuscan landscape. A few blocks south, the National Picture Gallery houses a vast collection of Sienese masterpieces, while nearby, on Via del Capitano and Via di Citta streets, find some of the best Italian eateries serving up fresh fare from the region.
Civetta (Owl) — Directly to the north of del Campo, Civetta is home to the Romanesque Church of St. Christopher and the Palazzo Tolomei, an imposing Gothic palace and one of the oldest buildings in the city. However, today, Civetta is best known as one of the top shopping districts in Siena, with boutiques selling leather handbags, designer sunglasses, and handmade shoes lining Banchi di Sopra and surrounding streets.
Drago (Dragon) — To the northwest of Civetta, the colorful lanes of Drago eventually lead to the stadium, where the city’s sports fans come out in droves to cheer on the Robur Siena soccer team. Directly behind the stadium stands the Medicea Fortress, a 16th-century fort with an amphitheater, hiking trails, and panoramic views.
Giraffa (Giraffe) — Giraffa, to the northeast of Civetta, is one of the city’s largest districts, home to both the Santa Maria in Provenzano Church and the Gothic San Francisco Basilica. While much of the rest of the neighborhood is farmland and gardens, a stroll down Via dei Rossi will bring you by rustic eateries and quaint gelato shops.
Oca (Goose) — West of Civetta and south of Drago, Oca is home to the Basilica of San Domenico, one of the most important churches in the entire city. Here, just down the street from the birthplace of St. Catherine, you can see relics of the theologian, including her preserved head. Outside the basilica, take time to admire the Gothic arches of the impressive Branda Fountain, or grab a glass of chianti at one of the neighborhood’s wine bars.
Tartuca (Tortoise) — On the southwest border of the historic center, Tartuca is where you’ll find Siena’s stunning 19th-century Botanic Garden, lying in a green valley within the city’s ancient walls. For a nominal fee, you can step inside to see more than 2,000 species of plants, from those native to the Tuscan region to exotic flowers from all around the world.
Torre (Tower) — Jutting southeast behind the Pubblico Palace, Torre is a quiet neighborhood with cozy spots to grab lunch or dinner or take in some live music. Come here on Wednesday or Sunday mornings when the Piazza Mercato turns into an open-air market selling fresh flowers, ripe produce, and beautiful antiques.
Soak in the awe-inspiring sights of the unspoiled Tuscan countryside from high up in the sky. In a colorful hot air balloon, soar over the region at up to 2,000 feet (610 m), watching as the sun’s warm rays light up the emerald hills and sprawling valleys. Grab your camera to snap photos of the lush landscape dotted with old walled towns, hilltop castles, and verdant vineyards. Once back on ground, toast to the unforgettable experience with a glass of sparkling Italian wine.
Immerse yourself in the history and culture of ancient Siena on a walking tour with a local guide. Take a stroll through the heart of the medieval city, uncovering its most magnificent sites and significant landmarks. With your expert guide leading you down winding streets, marvel at the vivid mosaics of the Siena Cathedral and the treasure chest of Renaissance art within the Basilica of San Domenico. Visit one of the city’s contrada museums to gain insight into its traditions of communal life.
If you choose, opt to forgo the museum, instead getting admission into the Siena Cathedral. Make your way through the Gothic doors into a spectacular interior filled with ornate marble designs, colorful frescoes, baptismal fonts, and masterpieces by the likes of Michelangelo and Donatello. Or instead, choose to pair your walking tour with a gelato-making class to learn the secrets behind this beloved dessert.
Learn to cook like a true Tuscan in a workshop led by a master chef. Starting from scratch, roll up your sleeves and whip up authentic Italian recipes using local and seasonal ingredients. Slice crusty baguette and juicy tomatoes for classic bruschetta and knead the dough to make your own spaghetti. Once your creations are complete, settle in to savor the fruits of your labor with a mouthwatering glass of wine.
Speaking of wine, no trip to Siena is complete without heading out of town into the winemaking region of Tuscany. Leave the city behind in favor of the vine-covered fields of San Gimignano, Monteriggioni, and Montalcino. Travel into the countryside to sample its world-famous wine, with styles including rich brunello and tart chianti. Learn all about the winemaking process as you pair your sips with delectable bites of local salami and cheese.