Everyone talks about Siena, Italy, but not everyone understands why it’s so good ‘n’ sexy.
Good thing you’re here — ‘cause we do!
Siena is smack-dab in the heart of Tuscany, panini-d between the hills of Chianti and Montalcino.
It’s where you’re hardly ever indoors — unless you’re listening to late-night jazz or snacking on a Sienese sweet treat.
It’s where horses race in a sandy field twice a year in the main piazza, like its 1600.
And that’s just grazing the hot brick surface of its modern-medieval vibe.
We love day-tripping to Siena from Florence, and we wanna dish on why it’s worth it — and how to make it happen.
Think of this post as your mini guide to Siena’s awesome.
The Mini Siena, Italy Guide To Seeing, Staying & Doing in Siena
1. Siena’s old-school, come-hither vibe.
Even though Siena is a stone’s throw away from Florence, it’s nothing like it.
It’s smaller, and you can even walk to rolling Tuscan hills in the countryside in under 30 minutes.
Siena is painted with a brush of sepia, tones of red and peach, with a palace or cathedral here and there, bursting out of the brickwork.
Like nothing has changed in centuries.
Walking the backstreets of Siena really feels like you hopped into a Tuscan time machine, and dialed it back to a time where you bumped into royalty on the road.
It’s a testament to its layered history: Siena has battled with Florence over the years, and you can spot remnants of its wealth from back in the day. Plaques, neighborhood flags, coats of arms in the fountains and signs that have stubbornly held on since the 1600s.
It holds its own ground now, but scars from their feuds with Florence are still totally visible!
Speaking of which:
2. Siena is the perfect add-on to your Florence trip.
It’s hardly an hour’s drive away from Florence and makes for the perfect day trip and excuse to explore a new city for a night or two.
Here’s a hot tip, if you’re planning your Florence trip: you’re better off taking the bus from Florence to Siena, rather than a car or the train.
Why? The bus station in Siena is way closer to the historic center than the train, and it saves you more time for enjoying the city.
Here’s how to get to Siena from Florence:
By bus: SITA runs buses between Florence and Siena — its stop in Florence is across the street from Santa Maria Novella, the main train station. The bus stop for Siena is at Piazza Gramsci. It’ll cost €6-7 for a one-way ticket, and you’ll be there in about 1 hr 15 mins.
By train: You might have to change trains in Empoli on your way to Siena, and walk about 20 minutes across town, or take a 5-minute bus once you arrive. Mega-perk for a longer journey: the absolute best views! It’ll cost about €10 for a direct train to Siena, and will take about 1.5 hours.
By car: Renting a car at the end of your Florence leg is probably best — it’s not a city you’d want to try drive around in anyhow. Driving from Florence to Siena is a pretty 1 hr 15 min journey, cruising through Chianti. You can also hire a private driver.
Want to save time and have more fun while you’re in Florence? Grab our Florence City Guide here.
If you’re planning to stay a night or more in Siena, Italy here are our accommodation recommendations:
- Budget: Try Antica Torre, a cute three-star palazzo in a 16th-century tower! It’s small but calm and cheap. Pensione Palazzo Ravizza is another great option for staying close to the historic center.
- Hotel: We love Campo Regio Relais, a six-room hotel featuring fab details like silk curtains, linen sheets, antiques and lounges lined with books. Hotel Athena is an affordable option, too.
- Villa: Swim with olive groves as your backdrop at Villa Scacciapensieri, or on 18th-century grounds at the Hotel Garden Siena. Hard choices, we know.
3. Siena is more than pretty old buildings.
Small though it seems, Siena serves up a side of Tuscany that is all it’s own.
The usual suspects in Siena include strolling through the Piazza Del Campo, the Civic Museum, the Palazzo Pubblico and all the cathedrals… But you’ll figure that out real quick on your own.
We’re more into scoping out the nooks-and-crannies and undercover-cool activities to make our Siena trips extra-speciale.
If we could choose the most unique things to check out in Siena, Italy this list would be a great place to start:
- Try plan your trip to catch Il Palio. It’s a dramatic horse race and “battle” that transforms the main Piazza del Campo into a sand field. Siena’s different contrade (districts) compete for bragging rights and glory — as has been the tradition since the 14th century. Il Palio takes place twice a year: July 2 and August 16. Where else will you see a bunch of Italians duking it out on horses, fully liveried up?
- Walk 400 steps for a killer view of Siena. If you’re willing to work for it, climb the steps up Torre del Mangia (one of the tallest towers in Siena) to get a gorgeous view of the entire city — Piazza del Campo, the rolling hills and the Cathedral.
- Make a market run. The biggest market in Tuscany takes place every Wednesday at La Lizza, near the old fortress. You’ll find fab food, fashion and keepsakes to take home. Pro tip: try get there early in the morning (it’s open from 8.30am – 1.30pm) for first dibs on the goodies.
- Sneak into this secret room. While visiting the Cathedral di Santa Maria Assunta is a given (you can’t miss it), there’s a room in there that not everyone thinks to go to — the Piccolomini Library. The frescos here are vibrant, vivid and crazy detailed and their historic manuscripts on display are super cool.
- Truffle hunting in the woods. If strolling the woods of Siena with dogs sniffing out truffles sounds delightful, check out Siena Tartufi. Alessandro Pellegrini is truffle pro, and his little store has all kinds of truffle-flavored products like oil, patés, beer, honey and more if you’re not up for a truffle hunting tour.
- Spend a day drinking vino. The Antinori family opened the incredible glass-and-steel Antinori nel Chianti Classico complex near Siena to the public just a few years ago. Take a fascinating tour (make reservations) and then have lunch at their restaurant, Rinuccio 1180, perched on the roof of the winery.
- Thermal baths for two. Roll up to San Giovanni Rapolano Terme, and soak in natural hot springs overlooking the rolling hills and greenery of the Tuscan countryside.
If you want more of the same under-the-radar tips for Florence, you’ll find them all in our Florence City Guide.
4. Siena’s culinary scene (and nightlife) is sweet.
Siena has a sweet tooth, and we’re not mad about it. You’ll love snacking on Sienese desserts.
You must try panforte, a chewy gingerbread-y dessert with fruits and nuts and cavallucci and ricciarelli, local biscuits made with spices, almond flour, and vanilla icing.
… But save dessert for after you get comfy with a big bowl of pici — thick, hand-rolled pasta that’s basically fat spaghetti.
Siena is also one of the Italian cities that comes to life in the evening (thanks to its student population), so if you wanna dance and enjoy drinks over live music, this is the place.
Our ideal evening in Siena, Italy would look a little lil’ like this:
Start with a glass of wine (and people-watching) at Bar Il Palio, outside in Piazza Del Campo.
Next, head over to Vivace at sunset, for a tasty dinner with a gorgeous view of the city. Order any pasta — they’re all fab.
Then walk into unTUBO, to enjoy live music and of course, more vino. It’s one of the best spots for live music in Siena, so make a reservation in advance if you wanna check it out.
If you’ve had your fill of pici and Montalcino and are ready to wind down, make a stop at the Tea Room — a popular late-night and all-day hangout for desserts, a huge selection of tea (obvi) and super cute ambiance.
More great spots we recommend for dining out in Siena, Italy:
Casual eats: San Paolo Pub, Il Bandierino, Pizzeria Poppi.
Traditional trattorias: Antica Trattoria Papei, Taverna di Cecco, La Taverna di San Giuseppe.
Scenic lunches: Osteria Le Logge, Ristorante San Domenico, Vivace.
Fancy dinners: Tre Cristi, Castel Monastero, Ristorante Tar-Tufo.
5. Siena’s countryside is the best of two types of vino.
Everyone knows that when you visit Florence, you gotta hop in a Vespa or vintage Fiat and cruise through the hills of Chianti.
When you visit Siena, you get Chianti and Montalcino to choose from, because it’s right in the middle. Tripping through Siena’s countryside should probably be a Grand Tour of its own, featuring mandatory stopovers at hot springs.
Some of our fave things to do in the Sienese countryside include:
Strolling through nearby towns: Like Montepulciano and Pienza, to drink wine and eat pecorino cheese. Very important.
Making friends with winemaking families: Driving to Casanova, an organic family-owned winery to sample wine, balsamic vinegar, olive oil and cap it off with a multi-course lunch.
Walking to Rome (kinda): Hiking the old pilgrimage Via Francigena route for 5-10 km from Siena — this is the ancient road to Rome that weaves through England, France and Switzerland too!
Exploring Brunello di Montalcino: Making our way through the countryside of the Siena Crete and Val D’Orcia, ‘till we’re smack dab in the middle of Brunello, AKA wine heaven! Stop along the way to pop into vineyards, and look out for a huge fortress.
Unwinding after a big bowl of pici: By soaking in thermal waters with a killer view at San Giovanni Rapolano Terme.
How we can help you go to Siena
- Check out Gigi Guides, our digital guidebook. It’s chock-full of insider recommendations for nearby Florence, as well as the Cinque Terre, Venice and Rome.
- Ask us a question in the comments below and we’ll help you out!
Feel free to borrow our ideas for Siena, share our Siena, Italy guide with your friends, or print it out!
Want more insider intel on traveling Tuscany? Here you go:
Here are more blog posts too:
- What To Do In Florence
- The Top 10 Spots in Northern Italy (And Why You Should Go)
- Which Town in Tuscany Should I Visit?
- Things To Do In Florence
- The Only 2 Tuscany Itineraries You Need
Got questions about what to do and see in Siena, Italy?
Share with us in the comments below.