Tuscany by Car 🇮🇹 A Complete 7-Day Italy Road Trip

Tuscany by Car 🇮🇹 A Complete 7-Day Italy Road Trip

We’re spending 6 days road tripping 
through the incredible region of Tuscany. Oh my god, Look up straight ahead. And we’re doing it on a budget. Oh my god. Can I have a bite as well? Which is why we’ve chosen to visit in the shoulder   season of September instead of 
during the peak summer days. It’s just us. The weather’s changed. It was warm, so we dumped our jackets back in 
the car and now it’s cold again. But even though we do get some 
chilly weather during our trip, nothing could take away from the 
gorgeous medieval hilltop towns, the endless rolling vineyards, and of course, 
some of the best pasta and gelato we’ve ever had. But we won’t just be eating and 
wandering the gorgeous villages.   We’ll also be exploring Tuscany’s incredible 
natural beauty, as well as staying in some of the most unique accommodations we’ve ever 
experienced. Along the way, we’ll be sharing every detail and exactly how much we spent 
so that you can plan your trip to Tuscany. Good morning, beautiful people from Tuskany. Not 
just anywhere in Italy. We’re in bloody Tuscany and we’ve just started a 6 day road trip and 
we’ve made it to town. I don’t even know the name. Maxine Sanan Minato, which is apparently 
the world’s capital of truffle, which is my favorite type of pasta to eat. So, we’re going to 
go and try and find a restaurant that serves some truffle pasta. But already this Wow, this village 
is just a great start to this road trip. It’s so picturesque here. Amazing. Can’t wait. 6 days, 
guys. So, let’s get started with some delicious Italian food. So, it is 1:38, but like none of the 
restaurants look open. Do you think it’s because of the truffle? Oh, maybe there’s going to be a 
lot of in this next section of the video because it’s actually been so long since we’ve been in 
Europe. So, just being back in Europe and like the beautiful architecture and the narrow streets 
and all these little like vantages that they have, it’s just an overwhelming amount of beauty here. 
So beautiful and also surprisingly affordable. We rented a car and it’s only costing us like 15 
per day for the car rental and the accommodations along the way. They’re not like super crazy. 
We’ll be sharing all the accommodations we’re staying cuz I actually found some really cool 
accommodations which I cannot wait to show you   and experience myself. We’re here in October. 
Yeah, it’s still warm. Kids are back at school. There’s far less tourists, man. Well, I mean, I 
think there is. There’s just in this town there’s   nobody. Yeah. And let’s see if the restaurants 
are open then. Let’s go get some pasta. So, unfortunately, a lot of the restaurants 
are closed. We couldn’t get pasta,   but we did find this place that’s open. They 
don’t do pasta, but they do truffle paninis. Oh, yours looks so good. Cheers. delicious, but this sandwich is like €12. We were just trying to get something truffle, 
guys, in the capital of truffle. We’re trying   to make it work. Things don’t always work out 
when you’re traveling. We have 6 days of this road trip and so many opportunities 
to get some amazing Italian food. All right, let’s go have a quick look at this 
beautiful town. Max actually found a few   towns along the way to Sienna, and this is 
one of them. This is Cal Deal Deelsa. I know I’m butchering the pronunciation, but bear 
with me, guys. I’m trying. It looks stunning. My gosh. So, I just saw on the sign 
as we’re entering the historic center, there are four castles, four different churches or 
buildings of worship. I think one was a monastery up here and one theater in one tiny tiny little 
section. Oh my god, look at straight ahead. This is a lot to take in on day one. So this 
town is apparently the glass making capital of Italy. It is absolutely stunning. This little town 
actually this is like the alternative to one of the most popular towns to stop at in Tuscany which 
is San Gamo. And that’s one that we’re actually planning on going to tomorrow. Apparently, 
this one is quite similar in vibe and look, but way less touristy. So, we have two potential 
pathways. We could go down the beautiful lit sunny with a view. Gorgeous. Or there’s this unique 
one which is completely covered and has these like eerie looking lanterns in there. Which one? 
I want to do both. Wow, this is like medieval. I’m entering a castle right now. And to think that 
this is 6 or 700 years old. This is supposed to be one video of 6 days for a 6 day trip. And in 
one day, I think we can make one video already. Wow. This place is so adorable. That’s 
where we’re staying. Not sure exactly. Oh, I think this is it. We just walked into this 
really cute space and I think this is so cool. The accommodation is gorgeous. I haven’t seen the 
room yet, but just the setting is unreal. I’m so glad I booked to this one. So, now I’m going to go 
find Max, get our luggage, and we can go check in. Who’s coming? I know. Holy moly. Where we’re 
staying is actually a converted monastery and they’ve turned it into a hostel. This is so 
cool. Wow. The town is so tiny. There’s like two restaurants basically. The one at the host 
and then another one out on the street. So,   I think we’re going to go find somewhere to 
have dinner. H. It’s just such a unique place to stay. And we’ve actually stayed at a monastery 
before in our travels. When we were in Bulgaria, we stayed at the Rico Monastery, which was such 
a unique experience and one I highly recommend. It is an absolutely stunning monastery. 
So unique. But this one very cool as well. We are leaving our gorgeous hotel. It was very 
shortlived, but also a very unique and fun place to stay. We will drop a link in the description 
for this hotel. In case you’re using this as a guide to plan your own trip, we want to go do 
a hike this morning. There is what is supposed to be a gorgeous trail not far from here. So, 
I’m very excited. We got a little coffee and we’re ready to go. This is such a nice way 
to start day two in Tuscany. Oh my gosh, I can’t believe how clear and blue this water 
is. It is stunning. Already, we’re only 50 m into the trail and it’s stunning. And we’re just 
going to be following this gorgeous blue river   the whole way up to waterfalls, I believe. So, 
let’s go. I got my coffee ready to go. There’s a waterfall right there. Look at this. Wow. I’m 
freaking out how beautiful this is. Oh, wow. Right there. My god. Holy moly. Oh my god, it’s like Costa Rica vibes. And 
you think you go all the way to Lao for a beautiful waterfall, but you just have one in your 
backyard in Italy and there’s no one. Oh my god. I can’t I just cannot deal with this. Wow. It’s just so nice. Every single 
bend just keeps getting better   and better. Oh my god. It’s just 
There’s a rope. Yeah. Inviting All right, that hike was honestly a highlight of 
this trip so far, even though it’s only been one day in one morning. But now I’ve gotten changed 
into some regular clothes and we are making our way to the town called Sam Gano. I know I’m 
pronouncing it wrong, but this is one of the towns that I think is a highlight of Tuskanyany. 
And in this town is a gelato store that claims to have the best gelato in the world. So all of our 
drives today, I think we’ve got four stops planned and every drive is only like half an hour between 
each stop. So we’ve got plenty of time to explore. Oh my gosh. Wow. This one is definitely one 
of the more popular ones, but it’s gorgeous. This town is actually really, really pretty. 
So, San Gamo actually has a nickname which is called Medieval Manhattan. And the reason is 
is because of these tall towers that were built here. And they were built, I think, in the 
14th century. And they were built by wealthy families. And it was kind of like a status symbol 
like, oh, I lived in this really tall tower. So, originally there was 70 of them in this 
village and now there’s only 14 that remain,   but they’re like, I don’t know, like eight 
stories high. Like they’re very tall. Okay, so we’ve just spotted Geratria Dondi, 
which has apparently been voted the best ice cream in the world. I don’t know where these votes 
happen, guys. Like, who makes the votes as well? Panic. Panic. I know. It’s so busy and I get 
so much anxiety in busy ice cream stores. Pistachio. Okay. Pistachio. Oh, wow. Okay. 
Pistachio is really good, guys. The espresso is good, but nothing out of this world. Oh my god. 
Can I have a bite as well? I like it. Yeah, a good swap. I was like, if I get an espresso, it’s like 
buying a coffee at the same time. So, you know, it’s really good. Yum. And it actually 
wasn’t super expensive. It was €3.50   50 for the small ones, which is what we 
got. When in Italy, gelato every day, how does it get so pretty? Like, we just 
walk down the most pictures alley with an archway over the top and then 
just opens up to this view like We have made it to the fortress town of Monte 
Reioni. It is so stunning. As we were driving up, we could see it on the hill. And it’s completely 
surrounded by these walls behind me and these towers. Apparently, this town looks almost exactly 
the same as it did when it was built 800 years ago. Like, there’s been almost no renovations 
and it’s like a very authentic. Because of that, they actually film a lot of movie scenes. It’s 
pretty small, I think, but we’re going to have   a little explore around. And I mean, already 
just the entrance and the little square we’ve come into. It’s so nice. Wow. The town is 
absolutely gorgeous. It’s so I don’t know, just different from especially cuz we 
just came from Sang Gamjano, which was   like really tall buildings and here nothing’s 
over two stories. It’s really quaint and small. This one is clearly less on the tourist radar 
than the one that we were just at. And probably the one that we’re going to next as well. Where 
we’re going to next. Wow. A pretty short drive later and we made it to Sienna. Look at this 
town. She is huge. This in the background. It was just mindblowing. But we’re making our way up 
to that area. That’s actually Ilo, which is like the main square. And illapo in Italian actually 
means field. And I think because it’s so big, it’s like a big field. And it’s a really unique 
main square as well. We’ve just parked a little bit out of the main area cuz obviously parking 
was pretty affordable. It’s a 50 per hour, which is not crazy. And we also learned that you 
can’t park in yellow lines. Yellow lines are for residents, but blue lines are paid parking 
and white lines are free parking. So, when   you’re doing your road trip around Tuskin, keep 
that in mind. That’s a really good tip to know. Oh my. Oh my gosh. What? This is This is wild. This is incredible. 
Holy moly, bro. This is like one of the biggest main squares we’ve ever seen. Oh, man. This is 
incredible. Like smells really good here, too. It’s really pretty. So this is the town hall and 
this building that is from 1309 700 years old. Now it looks like there might be a sign here about 
going up the tower because I was pretty sure that you could go up the tower but when I was looking 
I couldn’t see anyone up there. Maybe it’s closed down for something. Let’s go have a look at the 
sign. Dang. It’s only closed for 4 days and we’re here on one of those days. So, you can go up that 
tower. It’s €10 for a ticket to get up there, which Europe is uh killing us at the moment 
with the low Australian dollar, man. So, we really got to pick and choose which things 
we’re going to do, but I guess it’s closed,   so it shows for us, which is in a way maybe 
a good thing. Wow, this is so impressive. Oh, they kind of match it. I did this 
on purpose. Switch my jumpers out. Every angle, everywhere you look is like 
such impressive buildings. Wow. Wow. Wow. So, Jacine’s found a very interesting spot. It’s 
like a water reserve because Sienna was actually very ahead of its time in terms of its aqueduct 
system because you can tell it’s a lot of hills, but they could get water all the way up to 
that square. So, it’s was very much ahead of   its time. So, Jacine dug a little deeper and 
found us an aqueduct fishing net. Wow. It’s like a pool. I know. It like makes me want to go 
swimming in here. Wow. This is so nice. That’s incredible. The water is so beautiful. 
Like the hike that we were just doing, like rougher blue, crystal clear. 
Like there’s gorgeous fishes there. Wow. Now, last night we arrived 
at our hotel. And this morning,   we woke up to the most beautiful view 
here in Tuskini. We’re staying at this uh it’s actually an olive oil and truffle 
resort. And they also have a winery. And it’s not in a town. It’s out on a farm, I 
guess, like in the hills in the vineyards. So, we had to drive a little bit out to get here, 
but it’s still very close to towns that we want to visit today. And I mean this was our morning 
view and now we’re making our way towards Pienza. So Panza is basically a major PR stance by a 
previous pope called Pope Pius I in the 15th century I believe. And basically he wanted his 
tiny little village to be the perfect example as to what Renaissance and uh encompassed encompassed 
and he basically had the whole city grid rebuilt. He had the whole size of the building rebuilt 
and apparently there’s a perfect frame and some say that the pope actually built the landscape 
and not the building so perfectly to make it so perfect. And we have to find it because it’s 
apparently the perfect Tuscan or Tuskani postcard. So you can tell that this village feels a 
little more modern which is like Max was   saying earlier this was built to reflect the 
Renaissance period whereas the other villages that we were visiting previously were more from 
medieval times. So back in the medieval times things were more built with purpose whereas 
in the Renaissance times things were built for the look and the opulence of things. And this 
village is extremely picturesque and pretty. Every single village so far has had such a 
unique vibe even though they’re all in the same region and like really they’re all like 
half an hour drive from each other. It’s just been amazing. So we’re looking on that square 
that palado where the perfect frame is. Can’t be too sure. It’s not like it’s a frame, you know, 
like you have those tourists things now with like   welcome to whatever. But the frame we have here 
looks pretty perfect. So I think this is it. We’ve just made it to Monte Puliano, which is not 
far from Pienza. Was only about a 20-minute drive. It’s a lot bigger than Penza and it’s kind of 
gone back to that more medieval style than like why I was saying Penza was more of a Renaissance 
style, but there’s so many beautiful alleyways. Case in point, this one just here that leads off 
to a view. And on the other side of the town, we just went out to a viewpoint and it was just 
spectacular cuz you’re so high up. And then this side of town, it’s like going down and you can 
see so far. It’s a really beautiful town. It’s not busy in the streets. There’s not that many 
people wandering around. Doesn’t feel like too   overcrowded like San Gagan or Unfortunately, it 
was super windy yesterday and it was freezing cold. So, after we explored those two villages 
pretty quickly, we actually made our way back to our hotel. This hotel is actually an olive oil 
and truffle farm. And so they have this little sort of like cabin style I guess cabin style barn 
style rooms that are just absolutely stunning with this amazing view. So I’ll definitely link this 
hotel because the view is everything. But today the weather is predicted to be much much better. 
So we are going to go and explore a little bit more today. So our old luggage finally broke. The 
handle actually completely came off, which made for a hilariously awkward travel day. And the 
timing could not have been more perfect because we had already ordered level eight luggage to be 
delivered. We’ve been traveling with this luggage through Italy and we are so happy for the upgrade. 
First of all, look at how much space we have. Max and I had been sharing a cabinsized luggage for 3 
years, and it was always over the carry-on weight limit anyway, so we had to check it. So, now we 
have this bigger one, we have the space that we need. Even though this is a small size check-in 
luggage, the smart interior layout is designed so well that we finally have space for all of 
our things without having to bite our zippers. The 360 Skinner wheels are so smooth and the 
handles are super sturdy. So, they’re so easy to roll around even on the Italian cobblestone 
streets. And they come with TSA approved locks to keep all of your valuables safe. But what I 
really love about them is they look like high-end luggage, but they’re actually really durable as 
well, which is definitely necessary for the way Max and I travel. This one has Germanmade the 
macacrolon polycarbonate material which means it’s durable and it’s lightweight so we can fit 
more in and still be under the limit. And Level 8 has really thought about the Traveler with their 
awardwinning Voyager collection. This wide angle handle design has maximized interior space to make 
it easier for packing. So, if you’re hunting for a reliable and sleek luggage, then scan the 
QR code on screen now or use the link in the description and make sure to use our code MJ10 for 
a cheeky discount. Level 8 ships free to the US, Canada, and Europe. And every single piece 
of luggage comes with a lifetime warranty, which honestly, it makes us feel a lot 
better after what happened to our last bag. Wow. Wow. Once again, we have just 
found the most picturesque, beautiful village. We’ve made a stop today 
at Monte Morano. And the village looks quite small. We were just looking at a map of it. I 
think we can probably walk around this entire   village in like 20 minutes. So, we’re going to 
try finding somewhere hopefully to have lunch. Oh my god. Oh my god. Every street, every street, 
every angle. Absolutely gorgeous. My gosh. So, we come to this region of Tuskini or this 
particular area um for something that we really want to do tomorrow morning. I’ll save it. 
We’ll share all of that tomorrow. But this   town is like a really cute little stop if you are 
coming to this area anyway. So, oh my god, this one as well. H every single little alleyway is so 
pretty. And it’s okay, Max. They have a gelatia. Oh my god, it’s too beautiful. No way. 
It’s just too beautiful. The stone work, like the beautiful arch doorways and windows, 
little gardens everywhere. Oh my god. It’s too much, Italy. No, this is 
this this is too much right now. Like,   stop it. Who do you think you 
are? Look at the fountain. That works. It’s probably 
800 years old. Still works. We were just saying that it’s getting really 
hard to like pick like our top villages that   we’ve visited so far on this road trip, but 
this one is just sliding right into number one. It’s just basically a fairy tale. This 
one is a fairy tale. And that coupled with the fact that we’re sharing this beautiful 
square here with only two other tourists, it’s amazing. I think it’s uh this one might be 
it. Well, that was the whole town of Monte Morano. very small, very picturesque. There is a total 
of two restaurants that are open at the moment. And there’s even a restaurant that had two 
Michelin stars, but it’s not open for lunch. Cute. It is cute. Hey over here. Well, as Jacqueline did all the 
bookings before making this trip happen, I have no idea where we were going to stay. And we 
just arrived at our new location. It is gorgeous. As I don’t know if you can tell even from the 
background, we have this gorgeous little villa.   It’s not the whole house unfortunately. But this 
whole area here, I don’t know if it’s private, but I mean it’s so big that could easily share. 
We got like an outdoor area like sun settings. Absolutely beautiful. And here is our villa. 
And then let me show you inside cuz it is just as gorgeous outside as it is inside. But we also 
have this little quaint I guess will be like our breakfast nook maybe on a warm day. And then as 
you walk in, you’re greeted by a kitchen, I mean tea coffee maker, more like it. Jackie is already 
trying to figure out the coffee machine. And then   as we make our way further and then what I presume 
is probably the highlight of this place is Yes, we haven’t even reached the highlight yet. There is a 
sauna. Sometimes in Europe you your accommodation is just never cheap in Europe. And then sometimes 
it’s also really awful. So, but everything here, even though we’re paying a bit more, 
everything’s been lovely. So, it’s been great. Today, we are on a sunrise mission. There is 
something that gets a little bit crowded in this region of Tuskanyany. 6:45 a.m. Very unItalian 
of us. Wa! That is crazy amount of steam. This is incredible. Oh my lord. Look at this. Oh. Yes, it’s warm. Ah. Oh my gosh, this is so nice. Good morning. I mean, look 
at this. Look where you are right now. It’s just gorgeous. It’s also free, by the way, 
guys. I don’t think they mentioned that,   but there’s no entrance fee for this. And it is 
open 24 hours a day, so you can come anytime. The parking, however, you do have to pay 
for up from 8:00 a.m. to 8:00 p.m. and it was €250 per hour. So, not exorbitant, which is 
pretty good. And just like that, the sun is up, you guys. It’s still so beautiful. 
I mean, come come look at this. But it’s definitely getting a little bit busier. 
It’s like still not busy. This was the best   way to start our day in Tas. We only have 
today and tomorrow left of our road trip, so we got to make the most of them. 
Off to another beautiful village. It’s just I am still blown away that every single 
village we visit. We’ve been doing this road trip for five days and every single village is 
blowing us away in like a different way. They’re all so unique. Just found another gorgeous 
one. We’re actually in the Tufo region of Tuskani, which means a lot of the towns are actually 
built up on top of these volcanic rocks.   This one is Petigliano. And we like came 
up over the hill on the other side and got this like amazing view of it over there. 
And then we drove up here and now we’re   going to explore. But tomorrow guys, I 
actually have another one that I think is going to be even more epic than 
this one. But first, let’s go visit. So before we entered this town, when 
we were looking from the viewpoint,   there was a sign that was explaining 
that there was a lot of these underground passageways built throughout this 
town. And I guess a lot of the towns   in this region that are built up on these 
volcanic rocks and we’ve just found one. So this village is actually nicknamed Little 
Jerusalem. And apparently the food here is very, very good. But we’re a little bit too early for 
lunch. It’s only 10:30. Oh my gosh. Once again, absolutely blown away by another village 
here. That was just unexpected. Can we please have unolo and ketto crema? 
We couldn’t resist getting a little treat cuz we haven’t had any 
pastries since we’ve been here. Well, yesterday after our beautiful sunrise 
mission to the gorgeous hot springs that we went to, we actually just drove had a picnic 
lunch by a lovely lake and got some gelato, of course. Um, and then we went to our apartment. 
Max, unfortunately, had to catch up on a wee bit of work. So, our final day of our road trip is 
going to be a jam-packed one. We have two towns that we are visiting today. The first one is 
Ovietto, which is where we have arrived. We’ve come nice and early. It’s only 9:30 a.m. and we 
wanted to do that to try and fit as much in as we could. One thing, which is the thing that I’m 
probably most excited about, is already open, is the Po D San Patritzio, which you probably have 
seen photos of this online at some point if you’ve been doing it like into travel or Instagram 
or something like that. It’s a famous well, and we’ll tell you more about the city in a 
minute, but basically this entire city has a   proper underground network of tunnels and 
passageways that people have created over centuries. So, this one is really unique. 
So, this well was built 500 years ago now, and it was built and commissioned by a pope, 
which was actually kicked out of Rome for some, I don’t know, church region. And it’s 53 
m deep. So, courage to see what it’s like. Wo! Holy Oh my god. Wa! That is spooky. 
What? So, one amazing engineering feat of this staircase is that has two staircase. 
So the mules that would get the water at the bottom would never have to like bump into each 
other because one would one way would go down   with the mules and the other would go up with 
the mules filled with water really like this one here. This is incredible. Wow. It is so 
beautiful and unique. It feels like something you would see in Harry Potter or like Lord of the 
Rings or something like that. Like as simple as this stay well system looks or sounds, it is 
just very very cool. And that’s 500 years old. We finally made it to the very bottom. And there’s 
still water in here. And it looks really clear, like good, healthy water. Oh my gosh. 
And it’s very wet. Oh my god. Wow. We must have just arrived right before a 
tour bus because there’s a lot of people   coming down right now. But, uh, if you can get 
there early, highly recommend because I think it would echo a lot and people talking would kind 
of take away from like the spookiness of it. So yeah, definitely try to 
get here as early as you can. So our options are 240 steps or take an elevator 
and then 170 steps. And Max obviously chose 240 steps. Our second stop of the day in 
Oette obviously is to delo and we bought the Ovietto city pass which gives us access 
to four different monuments and like things to see and do in the city. There’s a full pass 
that you can buy which is €27. I think it was €34. Gives you access to everything. But 
we just bought the €18 one and just went with like one of the options that included 
the majority of stuff we wanted to do. Oh, we see the cathedral actually. Cool. Wow. Wow. 
That’s impressive. Okay, that’s a nice view. Wow, that cathedral is so like wow. Yeah, it’s 
crazy how big it is in comparison to the way the town looks. It’s really ginormous. It 
looks really big for the size of the town. Yeah, that’s really interesting. So, we 
just realized it’s almost 11:00. So, we’re going to wait and see if the bell behind us 
rings. Maybe this bell doesn’t operate anymore. Yeah, the church bells are definitely going off. 
Luckily, it’s also the end of the mass probably cuz it’s not like the more 11 kings. It’s the 
end of prayer probably as well cuz it’s Sunday. Oh my gosh. Woo. That woke me up. On our fourth 
restaurant, we found something. Fourth, one, two, three. Yeah. Yeah. So, we went to four different 
restaurants and they were all fully booked out.   So, I guess because this town gets quite busy 
with tourists and it’s a Sunday, I’m guessing the locals kind of booked places and maybe we were 
just going to the ones that were the best. So, this one might not be the best because it’s 
not fully booked. But, you get what you get. Finally. We have finally from our very 
first day on this road trip, we wanted to get truffle pasta and it is our 
very last day and we are finally getting it. But this is a great place to get it because 
this town is actually known for this special type of pasta which is called amrichelli and 
it’s this thick kind of spaghetti like pasta and it just smells so good. Anyway, here we go. 
Oh my god. This has been six days in the making. Oh my god. Yum. Oh wow. That’s some serious al dente there. 
The pasta noodles are so thick and chewy, which I actually love. Those are delicious, guys. 
That chewy texture on the pasta is amazing. And the truffle sauce. Oh my god, there’s 
nothing better than truffle sauce. Okay,   after a delicious lunch, which honestly was 
amazing, time for either the highlight of the city or the second best thing after the well 
in the city. The facade alone is impressive. Absolutely beautiful. Oh, now Jacqueline 
did say this is the end of our road trip, but we are heading to Florence, which has a 
beautiful church facade there as well. So, just so you know, we are have 
another video coming out. Wow. So apparently this cathedral of DMO 
actually inspired Michelangelo’s sister painting which is a pretty big deal. 
Well that was the dwamo of Ovietto. Okay, we’ve just taken about a 25 minute 
drive from Otto and we’ve come to Sevita de Van Reio and wow, we might have saved the 
most unique town for last on this trip. This town is actually nicknamed the dying city of 
Italy. Kind of like Oviet. It’s built on one of those tough rocks which are those that 
volcanic stone. Wow, that’s impressive. Wa. But the reason it’s actually called the dying city 
of Italy is because this rock is crumbling away. The really unique thing about it is you actually 
can only enter the town via a pedestrian bridge. So there’s no cars or anything inside. It’s 
only by feet, by foot. So the actual town is super super tiny and there’s only a handful of 
residents who actually live in there still. And it’s mostly just kind of for tourism now. But it 
just the look of it is so cool. Oh wow, guys. This is the definitely the most unique village that 
we’ve entered in this trip. It’s so cool. Wow. We weren’t sure what to expect when we 
actually got here. Max was just saying   maybe one of those things that like you want 
to look at from afar, but once you’re inside, you’ve like lost the uniqueness and the appeal. 
And it’s €5 to just enter this city. So, this is the first one we’ve had to just pay to 
access. So, I think it’s going to be worth it. Wow. in terms of adorableness and like every single 
angle of this town being so picturesque and like the perfect Pinterest Instagram photo. 
I think this town might actually be the cutest one that we’ve been to. Maybe Montano 
was pretty yeah, pretty strong contender, but this one now we have recency bias, 
so this one is kind of winning that vote, but it’s absolutely worth coming here. This is 
actually the last stop on our road trip. After   this, we’re going to be returning our rental car 
and making our way to the city of Florence. So, obviously in a vlog like this, we can’t cover 
every single little detail. If you have any questions about road tripping in Tuscanyany, then 
leave them in the comments below. We’re more than   happy to answer. So, we rented our car through 
Discover Cars, which we highly recommend because they actually have a 48 hour cancellation. So, if 
something goes wrong, you won’t be charged. You can cancel within 48 hours of your booking. Plus, 
they definitely have the cheapest prices by far. We always shop around to find the best deal and 
Discover Cars does that for you because it will   give you the price of all the rental agencies in 
the city that you’re looking at. So, you’ll get the best price there. We’ll leave a link in the 
description below to Discover Cars. If you book   through our link, we do get a small commission, 
but there’s no extra cost to you guys. So, we really appreciate it if you guys support 
us by using our links. Thank you if you made   it that far. Honestly, we have loved Taskani. 
And if you’re interested in going to Italy, we actually are just starting. So, a 
lot of more Italian videos coming up.

We spent 7 days road-tripping through Tuscany, exploring Siena, San Gimignano, Pienza, Montepulciano, Saturnia’s hot springs, and Orvieto — but this time, during shoulder season.

Fewer crowds, cooler weather, and golden countryside views made it feel like we had Italy all to ourselves. From truffle pasta to world-class gelato, this is Tuscany — quieter, slower, and more beautiful than ever.

Was it worth it? Let’s find out. 🇮🇹

1️⃣ Monastery: https://booking.tpx.lu/1u799Jji
2️⃣ Olive Farm: https://booking.tpx.lu/K77IaWCB
3️⃣ Villa: https://booking.tpx.lu/vKW3zFTa

🧳 Level8: Big luggage: https://linkly.link/2HSv2
🛄 Luminous textured luggage: https://amzn.to/3WtEhmO

🚙 Discover car: https://linkly.link/2HLOW

00:00 – Intro: 6-Day Tuscany Road Trip
01:20 – San Miniato — Truffle Town (first stop)
06:05 – Monastery Stay — check-in & first impressions
08:29 – Elsa Trail Hike — waterfalls & blue pools
11:15 – San Gimignano — “Medieval Manhattan” & gelato
20:01 – Olive Oil & Truffle Farm — our farm stay
20:33 – Pienza — Renaissance views & the perfect frame
22:33 – Montepulciano — wine, viewpoints & alleyways
24:01 – Gear Break: Level8 luggage (sponsor)
26:17 – Montemerano — tiny fairytale village
29:18 – Tuscan Villa — private stay & sauna
30:44 – Saturnia Hot Springs — sunrise soak
32:39 – Pitigliano (Tufo region) — “Little Jerusalem” & tunnels
35:04 – Orvieto — Pozzo di San Patrizio & underground city
42:45 – Civita di Bagnoregio — the “Dying City” (final stop)
45:31 – Wrap up, rental return & trip tips

🎬 Episode 323 – Tuscany Road Trip

🎥 Subscribe to follow our time across Italy 🇬🇪

🎥 Filmed September 2025

📍 Next stop: Florence 🍝

WATCH FROM THE BEGINNING:
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✈️ Search Flights: https://skyscanner.pxf.io/e1qbj6
🎟️ Find Experiences: https://viator.tp.st/zpd9gE1f
📍BEST Hotel deals: https://booking.tp.st/pJVpcI8M
🚙 Car Rental Deals: https://www.discovercars.com/?a_aid=m…

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