Siena – it’s more charming than you can imagine, possibly my favourite city in Tuscany, over Florence (I know!) … what are the best things to do in Siena when you visit? Here’s an itinerary of how we spent our day. Although, I can’t wait to go back and spend longer in Siena.
The best things to do in Siena
Siena is one of those cities that you can easily wander around in. One of the best things you can do in Siena is give yourself time to get lost.
There’s plenty of little alleyways you’ll come across, walk up and down hills; around corners and discover magical old churches and homes.
Of course, the city boasts several highlights such as its cathedral and towers that rival those of its once-enemy, Florence.
You can sign up for a walking tour in Siena if time permits. Take in museums, galleries and history – there’s so much to do in Siena in a small space. I really did long for more time here.
Siena is pretty and oh-so-Instagrammable so take your time. Wear comfortable shoes and take water though, as it gets hot here in summer.
Find your way back
It’s fine to get lost but at some point you’ll want to find your way out of the old town again.
Before ticking off your own ‘things I want to do in Siena’ list, we strongly suggest that you arrange reliable roaming data for your trip here (and across all of Tuscany) because you can access Google Maps for directions.
Even then we found that we often landed up against a wall – unable to walk through, we combined tech with tips from locals to make our way.
In old cities, Google Maps can get a little confused, but it’s better than having no guide at all.
Food with a view
The old town centres on the extraordinary Piazza del Campo where people-watching becomes the thing to do in Siena.
There are over-priced restaurants selling mostly pizza and pasta that surround this area and you’re really only paying for the view.
Cooper discovered a one-off though, a pub called San Paolo which sells yummy toasted paninis, beer and boasts a small balcony overlooking the spectacle.
If you’re swift, you too can indulge for less! This pub opened just after midday when we were there. It was a great base to settle, grab a snack and figure out what we wanted to do to cover off other things to do in Siena before the end of the day.
For other options off the expensive tourist trail, keep an eye out for little bars and restaurants in the back streets, or even away from the old town and on the way towards where street traffic is allowed.
How to get to Siena
We’ve already mentioned in our clips and blogs that you are better off with a car in Tuscany.
Siena, like in Florence, strictly limits traffic in the old town so you need to park outside.
Some car parks charge around €35 per day!
The car park at the Siena train station is a bargain – we were only charged €2.50 for around eight hours.
To get to the old town from here though is about 25 minutes’ walk – usually not a problem for us but it’s up a very, very steep hill that’s also busy with traffic.
Jump on bus no. 3 or 10. The bus station is underneath the shopping centre (which conveniently, also has a big supermarket).
You need to buy a ticket from the transit machine that will cost about €1.20 (one way). It’s a bit tricky as it’s in Italian so aim for an ‘urban’ pass that comes to about this amount, or ask a local – they were so helpful, quite often walking us a distance to ensure we were on the right track!
Get off at the last stop or one closest to the old city centre – about five minutes bus ride from the train station.
Coming back, you need to find the bus station which is in a different place from where you get off the bus. Again, don’t forget to buy a ticket that will be zoned as ‘urban A’ for around €1.20 for a single.
Siena is a truly wonderful Italian find, and another example of the many lovely places in Italy we want to visit.
I somehow knew the word, but not the destination until now.
Highly recommended on your Italian travel itinerary.
Do you have questions or tips? Let us know in the comments.
We’ve dropped into the little town, Radda, about fifteen minutes drive from our Tuscany apartments courtesy To Tuscany, it’s a perfect April day and I think this has to be the best time to visit Tuscany! It’s just so special.
I’m sitting in the corner of Radda’s old village square at a bar called Palazzo Leopoldo.
Cooper’s suggestion that I find a shady spot was a good one. The midday sun floods across faded yellow walls and sunflower pots, proving April in Tuscany sparkles with its own touch of timeless elegance. It IS the best time to visit Tuscany.
A pleasant soundtrack of Goo Goo Dolls and Mary J Blige has turned into a string of ballads by Ed Sheeran – a fellow fan must be running this joint!
April – the best time to visit Tuscany
The light in Tuscany is as they say: golden, warm and soothing.
The sunsets across our To Tuscany apartments are spectacular and saturate with pretty light the rolling hills, olive groves and vineyards (which at present are stripped, a new season on the way).
It’s really warm in the middle of the day and a nice change from chilly England (that said, we’ve had nice days in London recently, we’d recommend exploring Kensington on a sunny day, or heading to a sky bar if you’re in town).
Where I sit and write now – first draft on paper – I’m positioned by an old Roman fountain.
I spotted a young artist perched by a flower pot sketching the fountain just the other day and thought how charming the scene was; now I’m here and feeling all creative too.
I don’t really mind if no one reads this – the space, the channel, the craft, it’s for me.
I guess right now though I’m bordering on an Under the Tuscan Sun cliché, but that’s ok too.
Three notepad pages down already, and they’re still playing Ed Sheeran. Lucky streak for me!
Last time I wrote like this was in my treasured travel diary from my first life-changing adventure back in 2000 which was to the USA and Canada.
I remember sitting inside McDonalds as freezing snow fell upon Times Square outside. First snow I’d ever seen.
A melodic Backstreet Boys tune played on the radio there (also good by me, at the time), and it was my first experience as a traveller being alone but not feeling lonely.
It’s a bit like that here too (although Cooper’s not far – he’s wandered off towards the scenic viewpoints on the outskirts of this pretty place to record a little something for YouTube).
Drops in temperature happen here too – overnight from around 4pm; but it’s light until 8pm.
To Tuscany apartments
Our villa is in Montebuoni, which is a ‘resort’ in the Tuscan hills, about 15 minutes’ drive from the nearest town of Radda in Chianti, and next door to an impressive winery, Castello di Ama.
We were staying here with To Tuscany in a cosy villa named La Stalla.
Montebuoni is set amidst hilly vineyards and includes pool, tennis courts and a number of beautifully restored villas, some of the original buildings date back to the 1500s.
We discovered that during medieval times, this whole area that had been popular for wine and olive producers, was mostly abandoned due to ongoing wars between neighbouring cities Florence and Siena.
It was unsafe to live here until the 1800s when things calmed again and people returned to the area, only to gradually regenerate it to its former glory.
Now the fields that stretch as far as the eye can see offer a patchwork of organised plantations that make the land look particularly charming and well kept.
I can actually see why many Italians were drawn to develop businesses in far north Queensland during post-war migration periods because the climate and land in that part of Australia feels quite similar to the Tuscan region. Tuscany’s landscape is larger though, but I felt some similarities and I remember quite well the Italian influence of my childhood in places like Cairns, Atherton and Mareeba (Australia); and the wine regions are a little similar to Australia’s climate, like in the Hunter Valley.
Iconic Italian Cypress trees point skyward and line the property around where we are staying; grassy spaces with wildflower patches are everywhere around us and we’re spoilt for choice when it comes to scenic picnic spots.
La Stalla’s most important feature for me was the peace and quiet.
The large, homely property sleeps four or five, and when we arrived on Monday I actually fell asleep on a bed in a little patch of sunshine that was streaming in through the window.
A bird sang sweetly outside, the wind gently swept across the trees and I couldn’t resist dozing in the warmth and stillness of it all.
No east London sirens, no deadlines, and happily no Wi-Fi.
I think we don’t realise the impact of city life until we remove ourselves from it.
I find the city’s energy and opportunities intoxicating but here I’ve remembered the pleasure of slowing down, just being and indulging in imagination; well, that and a bit of red wine (Chianti, of course) and cheese.
And when I say ‘a bit’, I quite possibly mean a lot.
You do need a car in these parts (automatic, and with a GPS or reliable phone data package for Google Maps is highly recommended).
There are many villages that would be difficult if not impossible to reach otherwise. You can visit wineries of all shapes and sizes, most family-owned and operated.
Gorgeous Siena is about 45 minutes’ drive away, and yesterday we parked there and took a train to Florence (find the car parking facility at Siena’s train station for about €2.50 for the day, which is vastly cheaper than anywhere else, and for trains visit trainline.eu).
Florence is beautiful.
If it weren’t for all the tourists it would be perfect.
It’s a small, romantic city in which you can walk around – everywhere takes about twenty minutes.
Florence is where the Renaissance began, breaking the shackles of the Dark Ages and shedding light once again on creativity, learning, passion, pleasure and the arts.
The city was famously managed by the Medici family in the 15th Century, and their mark along with that of the artists, musicians and papal folk that influenced during this time is still bright and bold.
Find a view – whether up the steep hill to absorb all that Piazzale Michelangelo has to offer, or from a cool rooftop bar position; breathe in the past and present indulgences of Florence.
There’s tours of all sorts here, and we’d strongly advise researching ahead of time to avoid the queues which can quickly become tiresome.
As for me today, I’ve recovered from the hustle and bustle of that big Italian draw-card and am happily hanging about within Radda’s romantic walled city with pen in hand, coffee at the ready.
It really is beautiful in these parts and while I don’t understand the language (yet) I find it soothing to listen to its rhythm in the voices of those around me or on the radio.
If you’re planning a trip to the region, I highly recommend To Tuscany’s apartments offering, and think that April is the perfect temperature and best time to come.
Signing off … I’ve got a date with Cooper at a winery.
Welcome to Travel Live learn, where we are passionate about living a life full of great adventures. We are Sarah + Cooper: we know life's short, and we're here to encourage you to make the most of it! We have worked in media, communication and creative roles for many years, and have spent over 10 years living and working abroad. Our hottest content topics here are pet friendly travel, house + pet sitting, and designing a life as expats or digital nomads wherever in the world you want to be. Join our community of over 11,000 like-minded adventurers - find out more by signing up for the mailing list and our Facebook Group. Find us on YouTube too. NEW podcast now live: search 'Freedom and Four Paws' on Apple podcasts, Spotify, Google podcasts or your fave podcast service provider.