My 2 Day Break in Siena, Tuscany

Welcome to Siena, an absolute gem in the crown of Tuscany. I didn’t know much about this town, I just knew I had always loved the name Siena for a little girl. Tuscany has always pulled at my heartstrings, I had previously been to Florence, Pisa and Lucca and loved them all, so I thought why not add siena onto my trip?

Siena is one of the most well-preserved Gothic cities in Europe, this is in part thanks to two things. firstly, the economic downturn of Siena during its Medici rule meant there were no funds to demolish and refurb the city. Secondly, the French took Siena in WWII with next to no damage.

Firstly, it’s important to note Siena does not have an airport, the best place to fly into is Florence as you can take a direct train from Florence to Siena. The train station is smallish but that makes it a little easier to navigate. I arrived by train after I took a service to Bologna (I had to change at Florence) and hopped into a taxi straight into the city centre.

The taxi took around 15 minutes and whilst you wouldn’t guess it from the suburbs, the Medieval town centre has very narrow streets so it’s easy to get stuck behind someone that can hold up your journey. I wasn’t exactly sure of the address of my Air Bnb so I asked my taxi driver to drop me off on the main Square, Piazza del Campo and then I would figure it out from there.

The piazza is absolutely stunning, overlooked by a beautiful tower on one side and surrounded by shops and restaurants on the rest of the three sides. The sun was shining and it felt like a typical spring day, I instantly knew it was a good idea adding Siena to my itinerary.

Once I figured out where my Air Bnb was I dragged my case across the square, up some stairs and into the main road that loops round the centre. It was pretty easy to find but it’s always good to have data on your phone so you can always know you’re in the right spot.

Once at the apartment I was faced with almost 7 steps up to my floor, I had booked on on the fourth floor as I heard the view was good. This was daunting, my suitcase had a big orange stick slapped onto it by the check-in staff at Heathrow stating ‘HEAVY’, yes, this girl does not know how to pack light, especially in winter. I did my best, dragging my heavy load up the stairs and made it to the top and into the *Air Bnb.

I dumped my bag and instantly headed for the terrace, it was just as beautiful as the photos online, if not more. Not only did I have a panoramic view of Piazza del Campo but I could also see across the whole of the old town and onwards to the rolling Tuscan hills, an absolute dream!

After soaking up the view and freshening up I headed out into the town. It was around 1pm by now and the sun was still shining and the sky was a gorgeous vibrant blue. I didn’t have a set plan, I just went for a wander through the narrow streets and boy was I falling in love! Siena might be a Medieval town but there are some great shops!

Siena is bursting with cobbled streets and ancient buildings, it is split into 17 districts that each have their own name and colour. As you meander your way through town you might notice the flags change as you walk through different districts.

After having a browse I headed towards the Torre del Mangia, the tallest tower in Tuscany, where I climbed hundreds of steps to the top. The view was incredible and I would highly recommend it to anyone visiting. There is no time limit on how long you can spend at the top unlike a lot of towers, plus I had the whole platform to myself practically!

Whilst standing high above the ground, with a gentle breeze in my face, counting all of the numerous churches that poked out above terracotta roofs, I decided I would definitely be coming back. I only had one full day in Siena but this is a place I could see myself in for much longer, not to mention the beautiful countryside that surrounds you.

I would highly recommend coming in January, it was chilly but pleasant. Perhaps I was just lucky with the weather but it was nice to explore without being boiling hot. I can just imagine what it’s like in the summer… many of the restaurants even on the square were closed for winter and there was just a handful of people out and about.

In summer, from what I understand, the city is bursting with tourists and day trippers, but that’s okay, that adds atmosphere too! I always recommend waking up early and enjoying a destination for a couple of hours before everyone else is awake anyway.

I then walked around the streets some more and found the cathedral, famous for its mosaics inside, it is one of the most architecturally impressive buildings I have seen. It reminded me of Florence Cathedral, just on a smaller scale.

After gazing in awe at this architectural masterpiece, I decided I was hungry so popped into a pizzeria on the square. At first I was taken aback, ‘is that Nutella on a pizza?’ I ask. ‘Yes lady’ was the response. Then as I stepped inside, I saw pizzas with chips (fries) on, I told him I had never seen a pizza with chips on before (and quite frankly I never want to again) and the chef just chuckled and told me it was to please the Americans.

I’m not sure how many American’s I know that would eat a pizza covered in chips, or should I say fries, but hey, who am I to judge! Instead I just ordered a simple margarita and headed back to the apartment to sit on the terrace and enjoy the view.

The evening atmosphere is always great in European cities, I find the children go to bed much later and everyone is pretty chill, I love to hear the buzz of chatter down below and watch people playing on the street, it was the perfect spot to people watch and the pizza warmed my stomach.

After the pizza was finished I headed back inside to binge watch ‘Cheer’, the latest Netflix phenomenon and something my sister got me addicted too. It didn’t exactly make me feel great after stuffing my face with pizza but it was soon forgotten about as I headed to bed.

The next day was forecast to rain but I wasn’t going to let that put a damper on things (despite not packing an umbrella). I decided I was going to go to a nearby town for the day and decided on Montepulciano, a smaller town south east of Siena.

I needed to get the bus to the station (the station is around a 30 minute walk from the city centre and I didn’t want to waste tine) so went to Piazza Gramsci which is the main bus drop off and pick up for the city centre. I took the S10 (after asking a lot of people where I was supposed to go) to the station, I tried paying for a ticket but the bus driver didn’t really understand what I was saying and wave me away from him, telling me to go and sit down. I’m not sure if the buses are meant to be free but I never bought a ticket…

It took 10 mins to get to the station, I spoke to the train ticket seller who warned me that the station at Montepulciano was not near the town at all, apparently it was 20 minutes away by bus! I then spoke to the bus conductor at the station who told me there were hourly buses into the old centre from Montepulciano Station so I went back to by my ticket. I was then told the next train would be in 2 hours! Yes, 2 hours.

I thought that won’t do and decided maybe it would be easier to just hire a car, Montepulciano is just one hour away by road anyway. Just as I was about to book the car hire, I remembered I had left my driving license at home in England… helpful, not.

After more hasty googling (I HATE wasting time, especially when I only have one day), I decided I would go to San Gimignano I had been wanting to go for years anyway. Similar to Montepucliano, San Gimignano is an ancient hill top town with no station, but there are buses from nearby Poggibonsi and the trains from Siena to Poggibonsi were much more frequent so I bought a ticket. My train ticket was something like €9, the trains in Italy are much cheaper than ours in the UK, and I was able to get on it straight away.

On arrival into Poggibonsi, you must head towards the bar/shop at the station and buy the bus ticket to San Gimignano. Annoyingly I had just missed a bus so had to wait an hour for the next, but I was able to sit with a cup of tea in the cafe so I hadn’t lost hope. It was pretty simple to find the right bus when it was time, firstly, there was only one, and secondly it said ‘San Gimignano’ in big capital letters on a piece of paper in the front. The bus journey took around 15 minutes, no one checked my ticket but it had only cost €2.50 anyway.

I arrived into San Gimignano and felt extremely lucky, the sun was shining and there was barely a soul to be seen. I did the same as I did when I arrived into Siena, I went for a walk, armed with just my camera and a podcast through my headphones.

San Gimignano is one of Tuscany’s highlights, it’s well known for its 14 towers rising up within the town’s walls. The city is beautiful and unique, it has been a UNESCO site since the 1990s but is fairly small with just 8,000 inhabitants. You may wonder why there are so many towers, yet a few hundred years ago there was over 70! The towers were built as a way for families to flaunt their wealth, competing with their neighbours for height.

I first did a loop around the centre of the town as it offered incredible views across the countryside, and for half my walk I was followed by a rather friendly cat. The weather started to get a little overcast at this point so I thought I would find somewhere for lunch. However, upon closer inspection, almost everywhere was closed. This is the downside to travelling in winter, you might get it with no people, but it means for many businesses, there is just no point in staying open.

For those travelling in more balmy temperatures, make your way across the central piazza to find Gelateria Dondoli, a gelato shop that has twice won ‘The Best Gelato in the World’. Unfortunately I couldn’t taste it for myself but I’ve never heard of a better reason to go back.

I then found myself outside the bell tower so thought why not? I purchased my ticket at €9 and ascended around 220 steps to the top. The last section is the hardest, it’s more of a ladder than actual steps and anyone over 5 ft needs to watch their head! All is worth it, not only is the town beautiful from above, but so is the countryside.

Once again I had it all to myself so spent 20 minutes taking photos and watching the birds flit from tower to tower. The bell tower (Torre Grossa) is the only public tower in the town and the only one you can climb, I can imagine there is a bit of a queue in summer as the top is fairly limited on how many people it can hold.

It was whilst I was at the top, just before making my descent I noticed the cafe at the bottom was open. With my belly rumbling I hastily made my way down and took a seat in the cafe. The menu was full of classics like tagliatele ragu and paninis, the staff were exceptionally friendly but the food itself was a little bland. I’m sure there are better places to eat but I wasn’t exactly inundated with open restaurants. I did get a nice biscuit at the end though, the cafe double as a patisserie and had some delicious sweet treats so I decided to take one for the road.

The precise name of the biscuit was ‘Occhio di Bue’ and I kept seeing this all over Italy and I had to have one! They are as delicious as they look on the outside and it’s definitely something I wish was more popular back home!

I looked up what time the bus back to Poggibonsi was and realised I was right on time to catch the 15:01, with a few minutes to spare too. I found myself a narrow street that led the way, and one I hadn’t yet been down, like all the streets in this sweet own, every nook and cranny was worth photographing. Upon leaving the street I could see the bus stop, then the bus approaching, I looked at the time and saw I had 3 minutes until it left, but I ran anyway, just incase. Low and behold, the bus zipped off when I was moments from it, 2 minutes early.

I checked the next time of the bus and I had 40 minutes to kill. There are definitely worse places I could find myself stranded but unfortunately I chose the wrong shoes to wear for a day of walking. My ankle boots had rubbed all around my calf as the shoes were slightly too big, my calves were red raw and I was already hobbling (the running for the bus didn’t help), but I soldiered on (where’s my medal?) and decided to enjoy one last view of the countryside before sitting at the bus stop early and waiting.

The next bus arrived without a drama and dropped me off at the station just in time for my train back to Siena. On arrival into Siena I wanted to get the bus back rather than a taxi (I would rather spend that money on food), but quite simply could not find the bus station despite a nice Italian lady giving me good directions. So I headed into a nearby shopping mall, bought some ankle socks to alleviate the pain in my calves and decided to walk back to the Air Bnb.

Bad choice, whilst the socks helped for approximately 5 minutes, they then kept slipping down, so I waddled my way home, put my feet up, and ate a bag of skittles for my dinner. Did I ever mention to never ask me for restaurant recommendations? I am fussy and have a very bland palette, I love to snack, I love sandwiches, I’m really not one for sit down meals unless I’m with a friend. However, if you want to ask me where to find the best cookie in a city, I’m sure I could tell you!

* My Air Bnb in Siena can be found here

Useful links

Train bookings in Europe: Trainline

Car hire: RentalCars

Hotel bookings:

Airport transfers: Kiwi taxis

Book trips and attractions: Getyourguide

Holiday home rentals: Vrbo

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