I got talking with Anna a few weeks before writing this, and within a minute she was three legends deep into the story of Siena. She is Tuscan born, speaks four languages, and has spent her whole career in tourism, first on hotel reception desks and later guiding, which means she has fielded every question a traveler can think of and enjoys the tricky ones most. So I asked her the one that counts. How would she spend a day showing someone the real Siena, past the crowds and the tourist menus? Here is her answer, with the legends, the food, and the corners she saves for people who want more than a photo of the Campo.
Meet Anna, Your Local in Siena
Anna grew up in the province around Siena rather than the old center, but the city has always been home, and she talks about its history the way other people talk about family. What pulled her to guiding with Lokafy was simple: she loves meeting curious travelers and watching them fall for the place she knows best.
She still remembers her first tour, a family from Boston she had been messaging on WhatsApp the day before about restaurants and local tips. They clicked right away, and by the end she knew this was the work she was meant to do. "It honestly feels like traveling the world without ever leaving my hometown," she says of the people she meets. That warmth is the whole point of a walk with Anna. Less rushing between sights, more time to actually talk.
What Anna Loves Most About Siena
Siena's history is ancient and, as Anna puts it, truly its own. This is a city packed with legends, contrada rivalries, and stories that most visitors walk straight past on their way to the cathedral. Her favorite thing to do is slow travelers down long enough to notice them.
That matters here more than in most places. Siena and its Tuscan neighbors draw big summer crowds, and it is easy to see only the surface. The version worth remembering usually sits a few streets off the main route, in a quiet contrada or a valley you would never guess was there.
The Legend Anna Starts Every Tour With
Anna likes to open with how the city began. Legend has it that Siena was founded by the brothers Senius and Aschius, sons of Remus and nephews of Romulus, who fled Rome after their father was killed and carried off the statue of the she-wolf. That is how Siena came to share Rome's she-wolf as its own emblem, and the black and white horses the brothers rode are said to explain the city's black-and-white shield, the balzana. Anna's favorite detail is the neat contrast that follows: Rome sprawls across seven hills, while Siena rises on three.
The legend itself took shape centuries later, and archaeologists trace the real Siena to Etruscan and then Roman settlement. But the story still explains what you see everywhere once you know to look, the she-wolf statues perched on columns and corners, the black-and-white banners, the split shields on the civic buildings. It is the key that unlocks the whole old town, which is why Anna hands it to you first.
A Local's Siena, Beyond the Piazza del Campo
Everyone starts at the Piazza del Campo, and rightly so. The shell-shaped square, the Palazzo Pubblico, and the tall Torre del Mangia are the heart of the city. Climb the tower early if you want the view without the queue.
The thing to understand next is the contrade, Siena's seventeen historic neighborhoods, each with its own colors, emblem, church, and fierce loyalty. They come to a head twice a year at the Palio di Siena, the bareback horse race run around the Campo on 2 July and 16 August. Ten of the seventeen contrade race each time, and the winner takes home a hand-painted silk banner rather than any prize money. Even outside race days you feel the contrade everywhere, in the flags overhead and the plaques marking each district's boundary. Ask Anna which contrada you are standing in and she will tell you its rivals too.
For a break from the stone, Anna points people toward two green corners most visitors miss:
- Orto de' Pecci sits in a quiet valley a ten-minute walk below the Campo, a community cooperative with allotment gardens, grazing animals, and a simple farm restaurant. It is hard to believe you are minutes from the center. Locals come to sit under the trees, and it is one of the calmest spots in the city.
- The Orto Botanico, Siena's botanical garden, runs cooler than the streets on a hot afternoon, and Sienese slip in with a book to wait out the midday heat.
A couple of small local habits worth copying: refill your water bottle at the public fountains, the Fonte Gaia on the Campo and the Casato spouts pour cold spring water, and time your gelato for Kopa Kabana on Via dei Rossi, a favorite among locals. On Wednesday mornings the open-air market at La Lizza, near the Medici fortress, fills with cheese, produce, and cured meats if you want picnic supplies.
Where to Eat Like a Sienese
Food, for Anna, is the fastest way into the real Italy. The dish to seek out is pici, thick hand-rolled pasta made from flour and water, a true staple of Sienese cooking. The classic sauces are all'aglione, a slow-cooked tomato and garlic sauce from the nearby Val di Chiana, and cacio e pepe, pecorino and black pepper. Anna's own top recommendation is pici all'aglione, and she is right to push it.
One local rule saves you from a tourist-trap meal: if a menu offers pici with a generic bolognese, look elsewhere. A proper Sienese ragù is made with wild boar (cinghiale) or the prized local Cinta Senese pork. Round out the table with crostini neri (chicken liver pâté on toast), ribollita (a thick bread and vegetable soup), and, for something sweet, ricciarelli almond biscuits or a slab of panforte, the dense spiced cake Siena is known for. Finish with cantucci dipped in Vin Santo.
Some spots that stay genuinely local, verified as trading in 2026, with hours that shift by season so a quick check before you go is wise:
- Osteria Il Grattacielo (Via dei Pontani), a tiny, unpretentious place serving Sienese since 1840, with a short menu that changes daily and locals filling the tables at lunch. Cheap, and the antipasto platter is a favorite.
- Antica Trattoria Papei (Piazza del Mercato, behind the Palazzo Pubblico), an old-school trattoria under brick vaults, strong on pici with wild boar and stewed cinghiale, with tables out along the street in summer.
- Trattoria La Torre (Via di Salicotto), a family-run spot near the Campo that locals name for its handmade pici all'aglione.
- La Taverna di San Giuseppe (Via Giovanni Duprè), a step up in polish and still a local favorite, known for pici, Florentine steak, wild boar stew, and a deep wine list in a cellar with Etruscan roots. Book ahead.
Anna's pleasure is matching guests to the right table, so tell her what you are in the mood for and she will steer you.
Anna's Tip: Get Out into the Tuscan Countryside
Her strongest piece of advice is to not stop at the city walls. Two medieval gems sit an easy trip away and make you feel like you have stepped back in time.
Monteriggioni is a tiny walled village on a hill a short drive north of Siena, its complete ring of medieval walls studded with towers. It was famous enough in its day that Dante used its towers as an image in the Inferno. You can walk the whole village in half an hour and the walls in not much more, which is part of the charm.
San Gimignano, a little further out, is the hill town of stone towers, a UNESCO site whose skyline of surviving medieval towers is unlike anywhere else in Tuscany. It is also home to the crisp local Vernaccia white wine and some championship-level gelato on the main square. Both towns pair well with a slow lunch and a look at the vineyards in between.
See Siena Through Anna's Eyes
The legends, the pici, the quiet valley below the Campo: these are a starting point, and they land differently when a local is the one walking you through them. That is what a tour with Anna is, a private, easygoing few hours shaped around what you care about, be it history, food, or the stories hiding in a single contrada, led by someone who would rather share a real meal and a good legend than march you past another checklist sight.
Book a walk with Anna in Siena and let a Tuscan local show you the city, and its countryside, the way she knows it.
Enjoyed this article?
