Continued from Bologna 2026 Day 4.

Late morning train, so we didn’t have to move too fast this morning.

Called an Uber van to take us to the train station. It’s a 10ish min walk, which is fine without luggage, but a real pain with luggage in the heat.

Oh look, a 911. Car spotting hasn’t been as good on this trip as I had hoped. Maybe it’s just because I’m staying in city centers and it’s just too cramped to drive their nice cars around here….except for London I guess. I still see nice cars everywhere in London.

At the station in no time.

Buy some lunch at a little cafe here to eat on the train. Ham and cheese sandwich is just…toast.

I wanted to have flexibility so I bought the tickets when I got to the station…I had a train company staff help me work the kiosk, and the kiosk stupidly assigned us to 2 or maybe 3 different cars. WTF. What’s worse is that it assigned two of the three kids on separate cars and I couldn’t even read the print out of one of the car numbers. We tried to resolve this in the ticket office, but they couldn’t do anything about it other than upgrade to business class seats since there weren’t any available seats. Well…I guess this is what I get for trying to stay flexible, it fucks me. This is stressful.

The staff told me that we should just go to the train, and talk to the staff on the train. They’ll make sure we all sit together since we are traveling with children and and people here are nice and will move for us to sit all together. Seems like it should work, but it’s made harder because I don’t speak Italian and what happens if for some reason we can’t all sit together or close by? Stress.

On the train now showing the staff onboard my predicament. Sure enough, he was very nice and said for sure we should sit together as a family, especially with young children. LKL was pretty worried actually that I would need to sit by myself at a car far away and I’d get lost and separated from the rest of them. I told him that it’s not them who should be worried about me, but the other way around. Either way, the staff found some empty seats for us close by in the same car and we were good to go!!

Coffee machine wasn’t working on the train.

At least the drinks machine was working so I could get some water.

My sandwich, does the job.

The ticketing staff who helped us with the kiosk was nice and wrote down in Italian what we should show the staff onboard in case they didn’t speak good English. But so far, a lot of people in Italy speak pretty good English so language barrier hasn’t really been an issue.

LKL loves ham.

Alright, here in Florence for a transfer. Of course, our train arrived a little late as per typical Italian train.

Our next train is already here, let’s do this.

At least it’s nice and cool on this train…at least in this section we are sitting at.

This looks like how I imagine Tuscany would look like.

He just can’t keep his hand to himself.

Daughter patting mama to sleep, sweet.

Do they trim these trees to look like this?

Another day, another heat record.

Then….our train stopped when we were maybe 20minutes away from Siena. We saw on the announcement that there’s an issue with the track signals or something like that and they had to do a reset. Some people starting leaving the train because they figured they could find a bus and take the rest of the way to Siena. We thought about it, but with 3 kids in tow and luggage, seems like it could turn into a nightmare if the buses show up overcrowded and we can’t get on. I guess we’ll wait….

Kids playing this game called chopsticks I think.

Our delay ended up being close to 2 hours. What started out as a 3 hour trip turn into almost 5 hours. That was miserable waiting on a crowded train without knowing if/when it would start moving again. Again…unreliable Italian trains.

We made it!!!

Everyone needed to go potty at the train station, so I’m watching over all of our packs.

Alright, let’s get a tax. We came out of the station to find this long long long taxi line. It’s not a long line if there was a stream of taxis, which there isn’t. One would come by maybe every 5 minutes, and with 5 of us and having to either take two taxis or wait for a large taxi, it’s looking like this could easily drag on to be an hour long wait. Tried calling an Uber van, but no one accepted the ride either…shit.

I know there are buses around here, but I haven’t done much research on how to ride them yet. Google Maps does tell you which bus to take and their timeline though. There’s a bus stop right in front of the train station, but it seems to be going the other direction that I’m headed, away from Siena. Everyone’s waiting there, I wonder if they are all going the wrong way without knowing? I went to a convenience store in the station where they sold bus tickets and asked where the other direction stop is at, and he pointed me in this direction…quite a long walk from the other station actually.

I hope this is the right station…the other direction is like a 3min walk away literally right in front of the station. I’m surprised this one is so far and also, we are the only ones waiting here.

Bus shows up and onward we go. It’s taken 30min since we got off the train to actually get on the bus due to the wait time with taxi and no Uber.

It’s a hilly town, so lots of turns. Lean against the wall LKL so you don’t fall.

And in about 10min, we are at our stop. That was pretty easy…except I’m now already thinking about how to get back to the station when it’s time for us to leave Siena in 3 days. I guess I’ve got 3 days to figure that one out.

Woah, what’s that on the other side.

Beautiful, made extra dramatic by the clouds.

Let me get a pic without the cars in the photo.

The bus dropped us off at the top of the hill, our Airbnb is at the bottom of the hill down these really long set of stairs.

Yeah, I’m going to nix taking the bus back to the train station. It’s already hard enough walking down these stairs with our packs on. It’ll be just that much more miserable going up hill.

Airbnb in sight, it’s that yellow building in the distance on the right of the picture.

Woah, beer garden? Actually, it’s the dining area for one of the contradas (districts) for the palio (horse race) that’s happening in about a week.

And next to the dining area is the yellow building of our Airbnb. Would be cool to be here for the Palio, but it also would be a lot having like 1000 people eating and drinking outside of the house every night.

Made it. What was supposed to be a relatively chill trip of 3 hours took much longer with the train delay and the taxi/uber wait times. That’s alright, it’s all about being able to pivot and change plans when traveling.

The key is stored in a lockbox on the side of the window.

This is what $538 a night gets you inside the city walls of Siena, but out of the core of the main old town. It’s alright, because we are situated right across from the escalators that takes you right up to Old Town.

All the girls loved the yellow tiles of this kitchen.

The kids room, with a loft.

There’s this extra bedroom room, but it doesn’t have AC.

RL and I will sleep here. Nice big room for us to spread out our luggage.

The view from our room. Beautiful.

One bathroom upstairs for us all to share. There is a full bathroom downstairs but this one is the one by all the bedrooms.

The loft upstairs. PL said that she’ll just sleep on the couch up here.

Garden in the back.

Looks awesome…except…I noticed mosquitos immediately. This area is off limits for me then, what a shame. Mosquitos hasn’t been an issue on this trip so far, but I guess this is the most “rural” we’ve been.

Downstairs bathroom. Nice to always have more than 1 shower.

Ha, die fucker! Kids, stop opening the doors, mosquitos are getting in!

Travel days always takes it out of us. We got here later than anticipated, so we’ll just chill and relax a little until dinner time. Good timing actually, it started raining while we are inside the house.

RL had bought a small bottle of prosecco at the train station which we now have split.

Rain’s stopped, time to go find some dinner and have a bit of a look at Siena.

Literally right across from our Airbnb are these escalators that will take us up the giant hill to the core of old town.

I think there are about maybe 7 or 8 sets of escalators. It’s very much appreciated.

It looks magical up here. We immediately like Siena. It also seems to be relatively quiet despite being a big tourist spot, doesn’t seem to be overrun by them.

Dinner spot.

Travel day tires everyone out.

I really like Menabrea beers. I remember when I came to Italy like 15 years ago, I saw Peroni everywhere. Maybe it’s because of the region, but so far I’ve only seen Menabrea and Moretti beers mostly (still a good bit of Peroni too).

Pork stew.

Lots of truffles on their menu here.

Yum, chickpeas. So simple, but so good. I need to make this dish at home.

Then we stock up at a little convenience store with bottles of water and beers and some snacks. We’ve been buying bottles of water everywhere we go, but really only for the containers. We refill the bottles with tap water and drink that, but when we change locations, we can’t bring 4 large bottles with us so we always have to buy new ones.

It’s hot, the kids have been getting so much ice cream this trip.

Alright, we are fed, we got ice cream and some supplies, time to go back down. I wanted to take a quick peek at the main square while we were up here, but was overruled by everyone else. Ok…fine, y’all win and I’ll go along.

The Siena cathedral up the hill, we’ll check it out tomorrow. Now it’s time to watch some Naruto at home and then go to sleep.

To be continued at Siena 2026 Day 2 Part 1.