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The rolling hills of Tuscany seem to extend forever, an endless sea of green punctuated by tall, slender cypress trees and medieval towers and turrets. As you traverse the countryside by car or bicycle, every turn in the road reveals a new postcard-perfect scene. Tiny ancient villages crown distant hilltops, beckoning you to explore their cobblestone streets and shaded piazzas. And everywhere you look, the iconic brick towers stand sentry, evoking Tuscany's medieval past.
These striking towers and turrets were built between the 12th and 15th centuries for defensive purposes, allowing villagers to spot approaching enemies from afar. Each village and noble family had their own watchtower, built tall and slender for maximum visibility. While warfare eventually ceased, the towers remained, leaving an indelible mark on the Tuscan landscape. They immediately conjure up visions of knights and maidens, battles and sieges. Nowadays the old towers have been converted into everything from private homes to restaurants and boutique hotels.
Climbing to the top of a tower rewards you with breathtaking 360 degree views over miles of undulating farmland, vineyards, and olive groves. The experience transports you back centuries, to a time when these towers protected local lords and their subjects. Gaze out across the patchwork hills and imagine the torch lights flickering in distant towers, warning of advancing adversaries. For the best views, head to San Gimignano, dubbed the "medieval Manhattan" for its forest of 14 well-preserved towers. Or visit Monteriggioni, whose complete ring of 14 towers and walls date back to the 13th century.
As you meander along the narrow cobblestone streets of Siena's historic center, it feels as if you've stepped back in time. Around every corner lies an architectural treasure, from striking Gothic palaces to intimate neighborhood churches. Unlike many Italian cities razed in World War II, Siena emerged largely unscathed, leaving its medieval and Renaissance core beautifully intact. Wandering these atmospheric alleys transports you to the height of Siena's artistic golden age.
Marvel at the clustered red brick facades lining the skinny lanes, punctuated by elaborate stonework and pointed Gothic archways. Stop to admire the 14th century Palazzo Tolomei, its facade adorned with ornate stone balconies and paired columns. Duck inside the intimate Basilica of San Domenico to glimpse Nicola Pisano"s lifelike 13th century carving of St. Catherine of Siena. The hushed nave drips with gilded frescoes and stained glass.
Emerging onto Piazza del Campo, your eyes lift to the staggering black and white marble facade of the Palazzo Pubblico, emblem of civic pride. Its Torre del Mangia bell tower juts 330 feet skyward, commanding sweeping views over terracotta rooftops for daring climbers. The soaring interior of the town"s cathedral stuns with striped walls of black and white marble, inlaid floors, and art by Michelangelo, Bernini, and Donatello. Even just weaving through Siena's neighborhoods rewards you with intimate medieval churches like Santa Maria dei Servi, richly frescoed oratories, and historic buildings adorned with sundials, coats of arms, and inscribed plaques.
No trip to Siena is complete without indulging in the city's delectable homemade sweets and baked goods. From panforte to ricciarelli, Sienese confections delight the palate while connecting you to centuries of tradition.
Panforte, a chewy confection chock full of nuts, spices, and dried fruit, has been produced in Siena since the 13th century. Its roots lie with nuns at the convent of San Domenico, who cooked up a cake using local ingredients like honey, flour, and nuts. The dessert's name comes from "pan forte," meaning strongly flavored bread. Biting into a wedge reveals a complex medley of flavors"hints of cinnamon, nutmeg, and cloves mingle with tart candied orange peel, crunchy toasted almonds, and chewy candied fruit.
Legend has it that ricciarelli cookies were created in the 14th century to celebrate the victory of Siena over Florence in the Battle of Montaperti. Their oval shape and indented center evoke a riccio or curly wig, in style at the time. Ricciarelli consists of a mound of ground almonds bound together by sugar and egg whites, then dusted with a snowy coating of powdered sugar. Their melt-in-your-mouth texture pairs perfectly with a cup of coffee or vin santo.
The best place to sample these treats is at local pasticcerie, or pastry shops, found on nearly every corner of Siena's historic center. At shops like Nannini, Panificio Il Magnifico, or Pasticceria Bini, cases brim with mounds of panforte, ricciarelli, and other homemade delights. Chat with the shopkeeper and you may discover even more obscure specialties.
Food tours offer a chance to indulge while learning about Sienese sweets and traditions from local guides. On Walks of Italy's Siena food tour, guests explore winding alleyways while sampling panforte, ricciarelli, and traditional snacks like caciunccoli, chunks of deep-fried batter. "Our guide Claudia was incredible - so knowledgeable," says Amy S. "The panforte from Nannini was melt-in-your-mouth delicious."
For an immersive experience, time your visit to coincide with La Festa del Panforte in November. The streets fill with locals sampling panforte, musical performances, a historical costume parade, and vendors selling the dessert. Or during Christmas, look for ricciarelli decorated with chocolate "R" initials at bakeries around town.
Each summer, the fierce medieval rivalry between Siena's contrade neighborhoods explodes onto the Campo for the adrenaline-charged Palio horse race. Dating back to the 1600s, the Palio transforms Siena's vast central piazza into a raucous racetrack, packed with frenzied spectators cheering on bareback jockeys sprinting clockwise around its perimeter.
For three days leading up to the big event, pageantry and competition build as each contrada parades in medieval garb, fueled by local pride and the desire for bragging rights. The race itself lasts just 90 seconds but rewards the winning neighborhood with a hand-painted banner known as a "palio" to display until the following year. Emotions run high during this brief but thrilling spectacle.
"From the moment we stepped onto the Campo, we were swept up in the electric energy of Palio night," recalls Jess, who traveled from London. "The thunder of horse hooves, bone-rattling flag throwing, and roar of the crowds celebrate centuries of tradition."
Visitors are awe-struck by the passion surrounding Palio and the all-consuming dedication to each contrada. Weeks before the race, trials assess the selected horses' speeds. Jockeys chosen to represent neighborhoods train intensely. Residents adorn streets with banners boasting their contrada's emblem"she-wolf, goose, owl, or more.
Come race day, attendees don traditional garb representing the 10 contrade. The Campo's perimeter fills with cheering, costumed locals who've waited all year for this moment. Troves of visitors flood the center, craning their necks for views of the treacherous tight corners. Finally, the horse and jockeys line up, ready to bolt when the rope drops.
In an instant, chaos erupts as the beasts surge forth, riders hanging dangerously off the sides while lashing each other with whips. The blink-and-you'll-miss-it race ends with the victor making a lap of honor, contrada members and fans flooding in behind. Next comes the awarding of the coveted banner, followed by raucous neighborhood celebrations flowing into the streets.
While the experience is exhilarating, animal welfare concerns have arisen regarding the Palio. Still, many defend it as upholding tradition. Travelers uncomfortable with the practices are best avoiding days when races occur. For those wishing to witness history, combining Palio with Siena's many cultural offerings can offer a balanced experience.
Among Siena's trove of Gothic treasures, none stuns quite like the alternating black and white marble facade of the city's magnificent cathedral. Constructed between the 14th and 15th centuries, the Duomo di Siena's intricately carved exterior stands as a testament to Sienese artistic ingenuity and pride.
The striking stripes of dark gray marble from Florence and creamy white marble from Siena coat the cathedral's lower and upper walls. Inlaid with delicate biblical scenes and statuary in each marble panel, the multicolored exterior resembles a meticulously decorated tiered cake. The effect almost seems to vibrate before your eyes.
"I must have spent at least half an hour just staring spellbound at the mindblowing facade, tracing every carved biblical scene with my eyes," recalls Sophie B., an art historian. "It brings such dynamic energy and beauty to a Gothic cathedral."
The upper facade greets visitors with busts of prophets and patriarchs watching over the Piazza del Duomo. Below, the lower facade's marble panels depict dramatic scenes from Genesis and the life of Christ. Tracing the story from left to right, Bilhah, Rachel, and other Old Testament figures give way to bustling images of the Nativity, the Adoration of the Magi, and the Massacre of the Innocents.
Throughout the facade, Siena's she-wolf emblem reminds all of the city's eternal glory. Even the cathedral's columns get their own distinctive black and white striped pattern, unique among Italian churches. Entering the cathedral through its northern doors, your eyes lift to take in the interior's stripes, arches, and golden mosaics with awe.
The origins of Siena Cathedral's one-of-a-kind marble facade stretch back to the cathedral's beginnings. Work began on the imposing Romanesque structure in 1215. As construction progressed over the next centuries, artists and architects expanded their vision into the commanding Gothic edifice visible today.
By 1339, financial woes threatened to stall work on the unfinished facade. The Black Death outbreak of 1348 further decimated funds and workers. But the proud Sienese refused to leave their cathedral bare and unfinished.
Inspired by the green and white marble trim of Orvieto Cathedral, architects designed Siena's signature black and white striped facade. The city decreed in 1366 that the facciata marmorea must be completed within the next decade"a lofty goal. To finance the marble, officials consolidated canons and sold holy relics. Despite the plague ravaging the population, artisans pressed on.
Siena spared no expense, decreeing that only the highest quality black and white marble adorn the house of the Virgin Mary. By 1382, workers finished the lower level. In the 1460s, they completed the upper facade and soaring loggia. Just imagine the jubilation when the facade was finally unveiled after over a century of fierce labor"a testament in stone to Siena's resilience.
Ascending to the top of the Torre del Mangia rewards intrepid climbers with jaw-dropping panoramic vistas over Siena"s sea of terracotta rooftops, providing a unique perspective on the city"s captivating medieval core. Built in 1325 next to the Palazzo Pubblico, the 325-foot tall brick tower dominates Siena"s skyline. Its lofty heights made it an ideal lookout point, allowing city officials to keep watch over the town below. Today, ascending the 500+ steps to the open-air viewing platform at the summit immerses you in centuries of history while offering Instagram-worthy views.
"Climbing the rickety wooden stairs of the Torre del Mangia gave me a new appreciation for medieval Siena," recounts Anne S. "As the view expanded at each winding turn, I glimpsed red-tiled rooftops, secret walled gardens, and distant church spires. It was like turning back the clock 600 years."
At the top, the city unfurls beneath you, its winding cobblestone lanes radiating out from the shell-shaped Piazza del Campo. Up close, it"s easy to lose your bearings in Siena"s maze of narrow alleys. But from this elevated vantage point, the neighborhoods reveal their hidden order. Gaze outward and pick out the major landmarks"the black and white striped Cathedral, the crenellated Town Hall, the historic churches.
Turn south and the dizzying view stretches for miles over the rolling hills of Tuscany, dotted with cypress trees and medieval watchtowers. On clear days, keen-eyed observers can even spot San Gimignano on the horizon, recognizable by its iconic towers. Meanwhile, peeking downward over the tower"s edges offers a thrilling overhead glimpse at visitors milling about in the Campo below, reduced to miniature size.
As you take in the 360 degree panorama, envision market stalls and medieval pageantry unfolding on the Campo over the centuries during Siena"s glory days. Picture processions of white oxen being led to sacrifice, or violent brawls erupting between feuding families. This very perch has witnessed it all throughout history. While many medieval towers crumbled over time, Torre del Mangia endures as a proud beacon.
The tickets to enter are well worth the nominal fee. But arrive early, as only 25 visitors at a time are permitted for safety reasons given the narrow stairs. Be prepared for the climb, as there are minimal places to stop and rest. "Going at a measured pace allowed me to save my energy for the endless steps," advises Jean R. "Reaching the top felt like a real sense of accomplishment!"
Keep an eye out for openings allowing small glimpses outward as you circle higher to stay motivated. The physical effort required to reach the rewarding views makes the experience all the more meaningful. Just be ready for crowds at the summit vying for unobstructed camera angles.
Siena"s acclaimed Pinacoteca Nazionale gallery houses a trove of priceless late medieval and Renaissance paintings and sculptures that provide a vivid window into the city"s artistic golden age. Wandering these hallowed halls allows you to come face to face with masterpieces from famed Sienese artists like Duccio di Buoninsegna, the Lorenzetti brothers, and Simone Martini.
"I was blown away by the incredible artworks at the Pinacoteca - it was like stepping back in time to the height of Siena"s artistic achievements," says Anne D., an art lover from Melbourne. "Seeing Duccio's MaestÃ¡ altarpiece up close was a spine-tingling, bucket list moment for me."
The gallery"s prized possession is Duccio di Buoninsegna"s striking Virgin and Child with Angels and Saints triptych, painted around 1300 for Siena"s Cathedral. Gaze in awe at the sheer gold leafing, precise brushwork, and emotional intensity of the Virgin"s delicate face. Tracing the individual biblical scenes depicted offers insight into medieval Sienese spirituality and striking Byzantine stylistic influences.
Don"t miss the Lorenzetti brothers" famous Allegory and Effects of Good and Bad Government frescoes, originally housed in the Palace of the Nine. These four surviving frescoes convey moral messages about governance through vivid, complex imagery of virtuous versus corrupt societies.
Other Pinacoteca highlights include Simone Martini"s ethereal Annunciation altarpiece and giant equestrian fresco of mercenary leader Guidoriccio da Fogliano, which captures the essence of medieval nobility. Extensive works by late Gothic masters like Matteo di Giovanni and vagabond painter Giovanni di Paolo reveal how artistic styles evolved into the 1500s.
Beyond the permanent collection, the Pinacoteca hosts world-class temporary exhibitions focused on Sienese artists. Time your visit right to view rare loaned works. Audio guides included with admission enrich the experience. Guided museum tours allow you to delve deeper with an expert.
After exploring the paintings, don"t miss the Pinacoteca"s sculpture collection housed next door in the solemn 14th century Church of San Agostino. Here, the expressive works of Jacopo della Quercia and lesser known Sienese sculptors line the nave in a sacred setting.
Beyond Siena's grand piazzas and famous monuments lies an intricate web of narrow backstreets and alleys that make up the city's historic contrade neighborhoods. Wandering aimlessly through these atmospheric corners of the city offers an intimate glimpse into local life, away from the tourist crowds. The contrade, 17 neighborhoods divided like pizza slices around the Campo, have deep roots stretching back to medieval times when they competed for power and prestige. While their rivalries play out dramatically during the Palio today, each contrada remains a tight-knit community with its own customs, small churches, symbols, and legacies.
Getting intentionally lost while exploring Siena's contrade on foot provides an opportunity to soak up authentic local flavor. As you weave through the narrow lanes, notice plaques on buildings announcing which contrada you have entered. Streets feature colorful emblems or murals celebrating that neighborhood's mascot, whether the caterpillar, unicorn, or goose. Flags hang proudly from windows marking the contrada's parish church, social club, and main public fountain.
Duck beneath arched passageways to emerge onto quiet residential squares with matching brick and stone facades. The pace slows to match the elderly residents chatting on benches. Children kick soccer balls against ancient walls. In the dimly lit oratories, aging frescoes tell stories of the contrada's history and miracles performed by its patron saint.
Listen closely and you may hear distant drums or horns echoing through the streets, signaling a neighborhood gathering. The contrade's passion plays out year-round through local rituals. Costumed parades transport spectators back to medieval times while building excitement for the Palio. Freshly painted horse statues get unveiled at contrada fountains during baptism ceremonies. Head into a neighborhood bar or osteria to watch residents young and old belting out their anthems over after-dinner limoncello.
"I loved exploring the narrow backstreets, never knowing what I might stumble upon next," says Amanda R. from Brisbane, who wandered Siena for a full day with no fixed itinerary. "In one contrada, I got invited into a courtyard to view a neighbor's private art collection. In another, I joined a chatty group of older locals passing around a bottle of homemade vino."
Alessandro P., who runs custom Palio-themed tours, recommends visitors take time to get lost. "No matter how many wrong turns you make, Siena's small historic center means you'll never stay lost for long," he says. "Slowing down this way allows you to experience the essence of these proud, time-honored neighborhoods."