TUSCANY ITALY TRAVEL GUIDE ‣‣ 5 Day Road Trip Itinerary

(ballad music)

- Hi friends!

Welcome back to another vlog.

We are on our way to Tuscany for the next four days.

Four or five days.

And I thought I would bring you along

because I haven't really done the vlogging

in a little while.

So, we just picked a rental car up in Rome.

We just spent five days in Rome

with some friends from New York.

So fun.

Absolutely loved it.

Had just the best time.

Now we are headed to Montepulciano.

So we are in the car for the next two hours

and then we're gonna have the rest of the day

to explore Montepulciano.

I think that this is gonna be a pretty drive

so I'm definitely gonna be showing you

some of the countryside.

And then of course, when we get to Montepulciano

you'll see that town.

(ballad music)

So we made it to Montepulciano

and parked our car, checked into our hotel.

I'll give you a tour afterwards,

but we are sitting down right now

at a little winery type thing.

I'll try to show you inside.

It's kind of busy right now.

We're gonna get a little food.

Have a little local wine

and it is absolutely stunning here.

I can't wait to show you guys around.

It is so beautiful.

We are at the top of a hill,

surrounded by vineyards and beautiful Tuscany.

It is probably one of the most beautiful towns in Italy

that I've been to yet.

I think you guys are gonna really like it.

(ballad music)

I didn't even Google this ahead of time.

I just saw that it was a cool winery.

But all of their pasta dishes are available gluten free.

They also have zucchini spaghetti

and they have different sauces.

So I'm gonna get gluten free pasta with tomato sauce.

(ballad music)

Alright, here we go.

Gluten free pasta.

Forgot to say no cheese, but that's fine.

I'll just eat around it.

Looks so good.


(gentle music)

So we just got back to our room

after walking around the town for a little while.

Let me make sure this is focused.

And I wanted to give you a little room tour.

I found this place on credit card points.

I have a Chase Sapphire Preserved card.

I can't remember exactly which one,

but it's really good for travel and you build up points.

I've been able to book a lot of hotels and airfare

through having points, which is awesome.

I found this place that way

and it's right downtown Montepulciano.

It's so pretty.

It's called Palazzo Cartelli.

Wait what's it called?

- [Male Voice] (mumbles)

- No.

- [Matt] Carletti.

- Carlatti?

- [Matt] letti.

- Carletti.

It's called Palazzo Carletti and it's an old,

I don't know if it was a palace.

But it's an old, basically building.

With very kind of ornate details and really beautiful rooms.

So let me show you our room.

You walk in here and then there is a staircase that goes up.

I actually haven't been up there yet.

I'll take you up there in a second.

But I think it's like a.

From what I can tell there's a t.v. right there.

It's like a chilling room.

Then you come in this way and there's a big bed.

A little chaise lounge,

I think are all kind of themed in a certain way.

So this is more pink themed.

We don't really have a view,

but you can just get a sense of the size.

It's literally humongous.

Then, I actually haven't been into the bathroom yet.

But the bathroom.

Whoa, lights (chuckles).

I guess there's different colored lights.

So yeah.

Oh my god!

These are tiny.

Whoa, there's a whole nother sleeping area up here.

So, there's a whole nother bed up here

and I didn't even know about it.

I will be coming up here tomorrow morning to work out.

This is so cool.

So yeah, this is our, I guess you could say hotel suite.

Much more than a room.

(mellow music)

I saved some of the gluten free bread from dinner.

I have my own almond butter and they have jam.

So I'm gonna do almond butter and jam.

Then I have a vegan coconut yogurt that I brought from Rome.

So I'm gonna have this too and a banana.

Good morning from day two in Tuscany.

We had our breakfast, which you saw.

I brought a few things with me

so I was able to do gluten and dairy free.

From here we are gonna drive to Pienza.

We're gonna walk down there a little bit.

Then we're gonna drive to our next location

which is a kind of spa resort outside San Gimignano.

I think we're just gonna end up chilling there

for the rest of the day.

We booked massages and I'm really feeling that.

I think it's gonna be beautiful.

But we are walking around right now

and another stunning Tuscan landscape.

(mellow music)

Just got to Pienza.

I have to carry my backpack around with me

when we stop at towns like this because

I can't risk having the car broken into

and I lose all my work stuff.

So I look like a winner with my backpack.

We are going to now explore this town.

So Pienza is known for pecorino cheese.

Obviously, I don't really eat cheese,

but pecorino is typically made with sheep's milk.

I'm pretty sure.

I'm thinking of romano, which I think is pecorino.

We'll see.

We'll see if we can maybe learn some more about it.

I've heard this is very a cheese focused town, kind of,

but also really pretty.

I'm excited to check it out and explore a little bit.

(mellow music)

So we just got to our hotel,

which is right outside of San Gimignano

and it is called Villa San Paola.

It's a wellness place with a spa

and just like the last one,

I got this on credit card points.

So that's a pretty great deal.

Gonna give you a little room tour.

So you walk in and we have one balcony here.

Look at that view.

And then in here, the bed is over there.

Another balcony here.

Then this way is the bathroom

and you can get in it from two ways.

So sink, shower, toilet over there.

Alright so the last couple hours just been chilling here.

I had some work that I needed to get done

so we booked massages pre-dinner.

Did a couple hours of work.

Had this amazing view behind me

and now we're gonna go downstairs to the spa

and get some massages.

(mellow music)

So the massages were great

and now we are having a little aperitivo

of local, organic (mumbles) wine and a beer for Matt.

Then we're getting dinner here at the hotel.

We're starting with the three artichoke something.

This one is definitely vegetarian,

and gluten free and dairy free.

Not sure what's on top of them.

Looks like maybe carrot, zucchini and I'm not sure.

Alright so here is the pumpkin risotto

with a little shrimp on top.

And again, gluten free, dairy free

and I have to tell you,

the artichokes that we had were absolutely incredible.

This looks so good too.

Okay so that was probably one of the best meals

that I've had in Italy so far.

I think partly because it was one of the more interesting

options that I've had, but flavors were really good.

The risotto was awesome.

The artichokes were really good.

Gluten free bread, good wine.

So we are gonna tuck in for the night.

It's (mumbles) 8:30 and we're gonna go to bed.

So tired.

And then, I'll see you guys in the morning.

Good morning friends.

Day three.


In Tuscany and we are on our way to Volterra.

We had a kind of slow morning.

I woke up and did a little P.volve workout.

I actually have a video that I filmed last week

for you that talks about my workout.

So if you're interested, I'll link it right up here.

Then I did a little bit of work.

We got breakfast down at the hotel,

which was actually really great.

They had roasted vegetables, hard boiled eggs.

Now we are on way to Volterra

and Volterra is a medieval city that's kind of built

at the top of a hill like a lot of Tuscan towns are.

And I went there two years ago with my mom.

It's so beautiful

so I'm really excited to check it out again.

We didn't have enough time last time.

Then tonight we are going to a vegan resort that is.

I think that it's like 15 minutes from our hotel.

It's a B&B type thing, but they also have dinners.

So they are hosting us for dinner

and it's a four course vegan dinner.

They said that they can cater to gluten free

so I'm super excited about that.

Unfortunately the weather is not great.

It's kind of sprinkling right now.

Hoping that the rain will hold off,

but it should be a really fun day regardless

and I'm excited to bring you guys along.

(chill music)

So we are about to walk upon a very ancient Roman theater.

This was the theater and then over there were

Ancient Roman baths and things like that.

You can still kind of see the shapes of them,

but this, I have to look online.

But I think it dates back over a thousand years

(chill music)

We're gonna have a little lunch

and this place is an organic bistro

that serves a lot of plant based food.

Vegetarian, vegan and they have gluten free.

Also on top of an archeological site.

We're walking on a glass floor and there's,

I don't know what, ruins or something underneath us.

Look at this.

So cool.

Alright, so I went with roasted vegetables, duh.

Some sort of rice and a salad

and I want to try this chickpea cheese

that they have on here.

Okay, so here is the cheese plate.

It comes with four different flavors.

There's a spicy one, natural, oregano, and pepper.

They are made from chickpeas and they come with also

some spicy onions, a carrot dip, a jam,

and they brought me some gluten free bread.

This looks so good.

Okay, so here is (mumbles).

It's good.

You basically just take one of these little Cheez-its,

which taste exactly like Parmesan.

Put it on my piece of bread,

add a little bit of the spicy onions,

and then I do a dollop of the carrot sauce.

And it's the perfect bite.

It's so good.

(chill music)

We made it to San Gimignano

and we're walking in the main piazza right now.

It's so pretty.

San Gimignano is actually also called the medieval Manhattan

because it has so many towers.

So I'll give you a view of this right now.

It's really beautiful.

We're on the hunt for some special gelato

that Matt really wants to try.

We'll see if we can find that.

I am on the hunt for a shoe store

that used to be in Volterra that is now here,

so I'm looking to get some more sandals.

(mellow music)

We just got to I Pini, I think it's what it's called.

It's the vegan resort

and they are gonna give us a little tour of the grounds

and then we're gonna have a four course vegan dinner.

I'm gonna go in and say hi to everybody and get started.

Here is the terrace and that over there my friends,

is San Gimignano.

Look at the beautiful pool they have over here.

(chill music)

The menu changes everyday and this is tonight's menu.

Four courses

and it all sounds incredible.


Here is course one.

It's a gluten free urban scallion pancake

with vegan Thai basil pesto,

which I'm definitely gonna recreate.

And marinated eggplants.

Course number two is a squash soup with gluten free croutons

and toasted seeds, fresh herbs, and it looks delicious.

Alright course three is a quinoa cake

with sweet potato wedges on top,

a veggie ragout and a lemon,

some sort of lemony sauce on top.

And course number four is an apple and plum

and ginger crumble with apricot sorbet.

They made a special gluten free crumble for me

and it looks so yummy.

(gentle music)

Good morning.

Back in the car and we are on our way to Il Borro.

Il Borro is actually something that I found out

through another YouTuber.

I saw that she went there and I knew that we were coming

and it just looked amazing.

Then a friend of mine went to Tuscany like, I don't know,

a couple weeks before us,

and also went there and said it was amazing.

So it is the splurge of Italy for me.

It's definitely gonna be a unique experience I think.

I don't really know what to expect,

but it looks absolutely amazing

and I'm super excited to check it out.

(upbeat music)

We made it to Il Borro and haven't even seen the room yet.

Haven't even really explored the property yet,

but wow.

It is so cool.

It's like it's own little oasis in the middle of Tuscany.

Own little town area where all of the rooms are.

It has restaurants, it has a spa, it has a gym.

It's just tucked in against a mountain in the countryside

and I can't wait to show you guys more

because this is definitely a special, special place

that if you're looking for a splurge,

I would say would be a good opportunity to do.

(gentle music)

And momma.

Hi momma.

Then over here.

This one is a 25-year-old donkey

who is so sweet.

You're so sweet.

You are so sweet.


Hi baby.

(upbeat music)

Hi guys.

We are on our way to truffle hunt

and I haven't vlogged at all yet today,

but we started the day with a really awesome workout.

Then we went for a delicious breakfast.

I had an awesome veggie filled omelet.

After that, we did a little bit of exploring

around the property.

And now we are on our way to truffle hunt.

The reason why I'm so excited to truffle hunt is because

Trevi's breed is bred to hunt for truffles here in Italy.

It's and Italian breed.

They're called Lagotto Romagnolos.

They're the best dogs on the planet.

They are cute.

You guys love her.

You see her all the time.

I don't know if there's gonna be one on this trip or not,

but it is led by dogs and I'm just like, fingers crossed.

The whole reason I signed up for this

is just the chance to see them in their natural habitat.

So let's hope that that's what we get to see

and also learn more about truffles

'cause truffles are amazing.

I'm gonna bring you guys along for the journey.

My camera is about to die so apologies in advanced

if the footage is not so great.

'Cause I'm gonna shoot it on my Iphone,

but hopefully it's fine and it's a really good experience.

- [Tour Guide] (mumbles)

Very soft, yeah bland.


No, no, it's a rock.

(Alyssa laughs)

- [Tour Guide] (speaks in Italian)

I have hit.


Possible cut.

Here is my truffle.


- [Alyssa] Little (laughs).

- Move (speaks Italian).

- [Matt] Go find more truffles.

- [Tour Guide] (mumbles)

Come on, go.

(speaks Italian)

- [Matt] Softer, she's softer.

That makes sense.

- [Tour Guide] Okay, good boy.

- [Matt] There's one.

- [Tour Guide] (speaks Italian)

- [Alyssa] So the second part of our tour is a tasting

and we're in this teeny little town

near where we searched for truffles.

Sitting at this restaurant all by ourselves.

And we're gonna have a little truffle feast.

Here are the fresh truffles that we harvested today.

Just some of them.

We got a total of 15.

Black, these are black, these are white,

and this is the one that smells the best.

- [Matt] Move your finger real quick.

- [Female Server] (speaks Italian)

- [Tour Guide] (speaks Italian)


And salt.

Is important salt.

- [Female Server] (speaks Italian)

- [Tour Guide] And little oil.

Top it.

Please, please.

- [Alyssa] It's good.

- [Matt] Oh it's so good.

- [Tour Guide] Yeah?

It's five here in the bottle.

- So I hope all of those clips were good,

but that was one of the best experiences that I've ever had.

It was so fun.

We just had the best time.

It felt so authentic and real.

He was great.

He was really helpful and knowledgeable.

We had that amazing spread of fresh truffles afterwards,

which neither of us really expected.

It was just an absolute incredible experience.

Even though we didn't have any Lagottos.

Well we met that one on the trail,

but Spilo was so smart.

He found us 15 total truffles.

And the other one, the little one was just the cutest.

It was really, really, really cool

and I'm so glad that we signed up and did it.

Now we are just gonna walk back to our room,

chill for a little bit,

and then tonight we are having a dinner

that is put together by the hotel.

They know that I am plant based so it's gonna be a special

veggie menu and I think it's gonna be.

Well, hopefully it's gonna be mostly vegan.

Mostly plant based

and made with all of their fresh organic vegetables.

Hi friends.

I just wanted to pop on and say goodbye

and sign off for this vlog.

I hope you guys enjoyed our travels through Tuscany.

It's definitely a must see.

If you're ever coming to Italy,

plan to spend some time here.

It's absolutely beautiful.

There's a ton to do

and it's just a really good mix of towns,

and that kind of thing, and also nature.

Really amazing food.

Awesome wine.

And there's just a ton to do.

I'll link everything that I've talked about down below.

I'm also gonna write a blog post

that includes our full itinerary,

so look for that down below as well.

I hope you guys enjoyed it.

None of this was sponsored by anybody.

I found all these places on my own

and like I said in the beginning,

I got some of them on credit card points,

so If that's something you're interested

in learning more about, let me know.

As always, make sure to follow along on Instagram,

which is where I'm sharing all of the other places

that I'm not vlogging

and I have highlights for all the things that we're doing

and eating.

That is all linked down below as well.

Otherwise, thank you guys so much for tuning in.

Don't forget to subscribe by hitting that red button

that is right below this video

and I'll see you guys in the next video.


(gentle music)