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:

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:

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

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:

Got questions about what to do and see in Siena, Italy?

Share with us in the comments below.


5 Responses

  1. Ciao Bianca, excellent recommendations that you have made! Living nearby, several favourite places to add to your very good choices are “Liberamente Osteria” right on the Piazza del Campo for a delicious lunch, brunch or dinner, and even better are their aperitivi at sunset! As you noted and recommended, on the Piazza del Campo the “Palazzo Pubblico” which houses the Civic Museum is truly worth going to for the amazing, fresco’ed palatial rooms. Close to Siena are the Chianti medieval hill towns of Radda in Chianti and Castellina in Chianti for good eating and shopping. While the Antiniori complex is quite interesting, it is closer to Florence than to Siena, and for a shorter drive (1/2 hr.) outside of Siena, the “Castello di Brolio” wine estate is truly worth visiting, both for the historical Ricasoli family’s contribution to the making (there is a small museum) of the Chianti Classico, as well as their excellent wines. They offer interesting wine related activities, including the new “e-bike” ride through the vineyards and the “strade bianche” (or back dirt roads) which is a fun and less tiring way to enjoy exploring hilly Chianti! Reservations can be made on their website, and are available May to October, and a little bonus is tasting three of their wines after the 4 hr. experience, as well as a visit to the gardens of the Castello. Their restaurant “Osteria del Castello” is very good and beautifully cool for eating ‘al fresco’ in the hot summer months. Buona giornata a tutti, e a presto. XO

    1. Wow Olga, GRAZIE for adding some great ideas to our list!

      We appreciate you 🙂

  2. We’re heading to Siena in May. Only have a couple of days but really looking forward to it as we had a few hours there a decade ago just after Palio and always wanted to go back. We’ve noted your recommendations!

Leave a Reply

Your email address will not be published. Required fields are marked *