21 Mar Tuscany Road Trip and Spello
I visited Tuscany in two separate trips.
The first time I landed in Pisa and took a short trip to Lucca. It was a quick glimpse, just enough to understand that Tuscany is not about ticking boxes, but about slowing down.
The second time I came back with a plan. A proper road trip that took me through some of the most beautiful places in the region: from San Gimignano and Siena to Val d’Orcia, Pienza, Montepulciano, Cortona and Florence, with a small but unforgettable detour to Spello.
What I want to do in this article is combine these two experiences into a single, complete itinerary — one that I genuinely believe is close to perfect if you want to see the best of Tuscany in one trip.
Pisa – Worth It or Not?
I spent two full days in Pisa, and to be honest, I have mixed feelings about it.
On one hand, it’s definitely worth seeing.
The Piazza dei Miracoli is impressive, and seeing the Leaning Tower in real life is one of those moments you kind of have to experience at least once.
I also enjoyed walking along the Arno River and getting a bit lost through the smaller streets, away from the main tourist area.
But at the same time, I’m not sure I would return for a longer stay.
If I were to do it again, I would probably spend just one day here — enough to see the main sights, take it slow, maybe have a walk through the city, and then move on.
Compared to other places in Tuscany, Pisa didn’t feel as special.
That being said, I still think it’s a very good starting point for the trip:
• easy access (airport)
• relaxed atmosphere
• perfect place to begin before heading deeper into Tuscany
Lucca – Where Tuscany Actually Begins
From Pisa, I took a bus to Lucca, and the trip itself was incredibly easy.
My accommodation in Pisa was perfectly located — right next to the entrance of Piazza dei Miracoli and just 50–100 meters from the bus station, with direct connections both to the airport and to Lucca.
And then… Lucca felt completely different.
This is where Tuscany really begins.
From the moment you enter the city, you get that cinematic feeling:
• narrow streets
• small passages opening into a central square
• medieval towers you can actually climb
It’s that kind of place where you don’t rush anything. You just walk, explore, and let yourself get lost.
Compared to Pisa, Lucca felt more authentic, more atmospheric, closer to what you imagine Tuscany to be.
If you have to choose, Lucca is a must.
For me, it’s easily one of the truly beautiful places in Tuscany and a perfect day trip if you’re based in Pisa.
If you’re based in Pisa and don’t want to deal with transport, there are also day trips from Pisa to Lucca you can check.
A Small Photo Stop: Castello del Boccale
The second time I arrived in Tuscany, after picking up the rental car from Pisa, I didn’t go straight into the classic route.
Before reaching Livorno, I made a quick stop at Castello del Boccale.
And this is something I would definitely recommend — especially if you’re into photography.
It’s the kind of place that can look completely different depending on the conditions:
• dramatic clouds
• stormy weather
• sunset or even night photography with long exposures
It’s not a place where you spend hours, but as a short stop, it’s absolutely worth it if you want something a bit different from the typical Tuscany villages.
Livorno – Worth a Stop?
After that, I continued to Livorno.
To be honest, this is probably one of the few places on this itinerary that didn’t really impress me.
I spent about half a day there and walked along the famous promenade, took a few photos, had something to eat and explored a bit of the streets
But overall, it felt quite crowded, a bit chaotic and surprisingly difficult when it came to parking.
I wouldn’t necessarily say you should skip it completely, especially since I didn’t spend enough time to fully explore it.
But at the same time, it’s not a place I would personally go back to or prioritize over other destinations in Tuscany.
Volterra – Tuscany’s Underrated Gem
Before reaching San Gimignano, I made a stop in Volterra.
And this is something I want to say from the start: Volterra is underrated.
Being so close to San Gimignano, it often stays in its shadow. Most people rush straight to the famous towers and skip it completely.
But for me, Volterra was absolutely beautiful.
It’s the kind of place where you actually feel Tuscany:
• quiet streets
• authentic atmosphere
• no crowds rushing past you
I arrived in the morning and for the first time I experienced that famous Tuscan fog. It completely changed the mood of the town.
Walking through those narrow streets, with almost no one around, stopping for a coffee and a pistachio croissant in a small local place — that was one of the most memorable moments of the trip.
If you ask me, Volterra is a place worth stopping for at least half a day.
Not just as a quick stop, but as a place where you slow down and actually enjoy the atmosphere.
Compared to San Gimignano:
• less crowded
• more relaxed
• more authentic
And definitely a place I would return to.
San Gimignano – The Classic Tuscany You Imagine
After Volterra, I arrived in San Gimignano. And this is where Tuscany starts to look exactly like you imagined it.
Those famous medieval towers, the narrow stone streets, the views over rolling hills — it’s all there.
I visited at the end of October – beginning of November.
There were quite a lot of tourists.
Not overwhelming, not unbearable — but definitely noticeable.
The key is not to rush it.
Why San Gimignano Is Special
San Gimignano is not just about walking through it.
It’s about experiencing it properly.
For me, the highlights were:
• climbing the towers and seeing Tuscany from above
• walking through the cobbled streets without a fixed plan
• stopping for a gelato from a place that was once named the best in the world
• and just sitting down in the evening with a prosecco, watching the sunset over the hills
That moment — sunset, a drink in hand, and that view — that’s when it really clicks.
Is It Overrated?
No. But it requires time.
If you just rush through it, take a few photos and leave, you’ll miss the point.
But if you start early, stay until sunset, explore slowly, climb the towers, get lost in the streets, then it becomes a truly memorable experience.
Val d’Orcia – The Real Tuscany
If there is one reason to do a road trip in Tuscany, this is it.
Val d’Orcia is, in my opinion, the real Tuscany.
Not just the towns, not just the architecture — but the landscape itself.
This is why I rented a car.
I wanted to be able to stop anywhere, at any moment, and capture those iconic scenes:
• rolling hills stretching endlessly
• perfectly aligned rows of cypress trees
• isolated villas sitting quietly in the middle of nowhere
Chasing the Perfect Shot
There were a few places I had in mind from the start.
The famous group of cypress trees, the well-known farm (Podere Baccoleno), those postcard locations you see everywhere.
But the truth is, some of the best moments didn’t happen at specific spots.
They happened in between.
Stopping randomly on the side of the road.
Seeing something that looked interesting.
Taking a break, grabbing a drink, and just enjoying the view.
Light, Weather and Expectations
Tuscany is often associated with:
• dramatic skies
• soft clouds
• golden light
We didn’t get any of that.
In seven days, there wasn’t a single cloud in the sky. Not even the smallest one. And yet, it was still beautiful.
Different, maybe not as dramatic for photography, but still incredibly peaceful.
Why This Is the Highlight of the Trip
Compared to the cities, where everything can feel crowded and structured, Val d’Orcia is the opposite.
This is where you slow down.
This is where you:
• drive without a strict plan
• stop whenever you want
• take a break on the side of the road
• have a small picnic
• open a bottle of prosecco
• and just enjoy the silence
This is Tuscany at its best.
Pienza – The Place I Wish I Stayed Longer
Pienza is one of those places that stays with you.
And if I had to describe it in the simplest way possible, it would be this:
I regret not staying longer.
It’s a small town, but that’s exactly what makes it special.
A Different Kind of Stop
By the time you reach Pienza, you’re already somewhere in the middle of the trip.
You’ve seen a lot. You’ve moved a lot. And this is the place where you finally slow down.
There’s no rush here. No pressure to see everything.
You just:
• walk through the quiet streets
• stop for a coffee or a gelato
• sit on the walls
• and look out over the rolling hills of Tuscany
Why It Feels Different
Pienza has a certain calmness that’s hard to explain.
It’s not about landmarks or “must-see” attractions.
It’s about how it makes you feel.
It’s the kind of place where you disconnect.
Where you stop planning the next stop and just enjoy the moment.
Would I Come Back?
Without a doubt.
Pienza is one of the places I would return to, just to spend more time, walk more slowly and enjoy it properly.
Montepulciano – A Second Chance Needed
Montepulciano is probably the hardest place for me to write about in this itinerary.
Not because it’s not beautiful, but because my experience there was… complicated.
When Things Don’t Go as Planned
We arrived on a very crowded day. And before even getting to explore the town, we spent around 40 minutes just trying to find a parking spot.
By the time we finally parked:
• we were already tired
• slightly frustrated
• and the mood wasn’t exactly ideal anymore
First Impressions
We didn’t get to explore everything.
Partly because of the situation, partly because we were already a bit drained.
From what I saw:
• beautiful streets
• lined with shops
• quite touristy in certain areas
But it didn’t have the same impact as other places on this trip.
Honest Opinion
I think it would be unfair to judge Montepulciano based only on this experience.
Sometimes, timing and context can completely change how a place feels.
I see it like this:
• based on this trip → I could easily skip it
• overall → it probably deserves another chance
And I do believe that many people genuinely love it.
Would I Return?
Yes.
But under different conditions:
• less crowded
• more time
• better energy
Because I feel like I haven’t really seen it properly yet.
Siena – The Place I Truly Loved
Siena was one of the highlights of this trip.
And not just because of the city itself, but because everything around it simply worked.
A Personal Connection
Part of the experience was also personal.
Some of the photos I took here ended up being among the most appreciated from the entire trip.
And that always creates a stronger connection with a place.
Staying in Siena
We decided to stay overnight in Siena, and that made a huge difference.
The hotel was excellent:
• very comfortable room
• great bed
• overall a feeling of being a bit… spoiled at this point in the trip
Parking wasn’t easy, but we got lucky.
We found a spot about 700 meters away — in a very crowded parking area — and managed to leave the car there for the stay.
Exploring the City
Siena is not the easiest city to walk.
Everything is built on hills, and you constantly go up and down.
You need a bit of physical condition.
But it’s worth it.
I loved:
• walking through the streets
• climbing up to the Duomo
• going up the tower
• and just getting lost in the city
A Reason to Come Back
There’s also something else.
Siena hosts the famous horse race, Palio di Siena, and that’s something I would love to come back and photograph one day.
Final Thoughts
Siena is one of those places that simply clicks.
Despite the effort it takes to explore it, it rewards you with atmosphere, views and a strong sense of place.
For me, it’s definitely a city worth visiting and staying in.
And without a doubt, one I would return to.
Cortona – Slowing Down Before the Final Stop
Cortona came at exactly the right moment in the trip.
After everything we had seen, after all the movement, this was the place where things started to slow down.
A Perfect Base
We stayed just at the entrance of the town, in a hotel that turned out to be a very good choice.
It made everything easy:
• quick access to the center
• no stress
• and a comfortable place to come back to
A Different Kind of Tuscany
Cortona felt:
• quieter
• more withdrawn
• easier to explore
It’s not a big place. You don’t need a plan. You don’t need a checklist. You just walk.
Simple Moments That Stay With You
Some of the best moments here were the simplest ones:
• eating really good food in small places
• enjoying those huge Aperol glasses
• walking through the streets without any pressure
And noticing the small details:
• laundry hanging from balconies
• old doors with peeling paint
• textures, colors, imperfections
That’s the kind of Tuscany I personally enjoy the most.
The Feeling of an Ending
Cortona also came with a certain feeling.
I knew that after this, only Florence was left.
The final push. The busy part. The famous part.
And this made Cortona even more special.
It gave me the space to slow down, relax and just enjoy the moment before the trip came to an end.
Spello – A Hidden Gem Worth the Detour
Spello was one of the places I wanted to see for a long time.
Mostly because of the flowers.
The colorful arrangements, the decorated streets, the small details that make this village so well known.
And even though I visited in October, it didn’t disappoint.
A Different Kind of Beauty
What I loved most about Spello was the contrast.
That mix between:
• raw stone walls
• narrow medieval streets
• and vibrant flowers everywhere
It creates something unique.
Every corner feels carefully composed, almost like a photograph waiting to happen.
When Plans Change
The initial plan was to visit both Spello and Assisi.
But things didn’t go as expected.
We spent around 25–40 minutes trying to find parking in Assisi, and it was simply impossible.
There was some kind of celebration, everything was full, and the police were redirecting traffic around the city.
So we gave up. And That Turned Out to Be the Right Decision
Instead, we spent more time in Spello. And honestly, I’m glad we did.
It allowed us to slow down, explore more and really enjoy the place.
A First Step Into Umbria
Spello felt like an introduction.
Not just to the village itself, but to the entire region of Umbria.
A region I definitely want to explore more in the future.
And if this was just the beginning, then I know I’ll be coming back.
Florence – The Grand Finale
Florence was the final stop of this trip. And it felt like it.
We arrived during a holiday period — I’m not even sure if it was a national celebration or something local — but the city was incredibly crowded.
At times, it felt overwhelming. We were lucky with our accommodation though. The hotel was just 200 meters from the Duomo, which made everything much easier in a city like Florence.
Is It Worth the Waiting?
We spent hours:
• waiting to enter the Duomo
• climbing to the top
• visiting the baptistery
• exploring the Uffizi Gallery
• checking all the iconic landmarks
And yes… the queues were long. But once you’re inside, you understand why. Florence is more than art. It’s overwhelming in the best possible way.
The Experience
Beyond the main attractions, Florence also delivered in other ways:
• great food
• long walks through the city
• that constant feeling that there’s always more to discover
It’s the kind of place where you realize very quickly that one visit is not enough.
A City to Return To
I know for sure I will come back. Maybe for a photography trip. Maybe for a football match — I would love to photograph Fiorentina one day.
Or maybe just to explore more of what I missed.
Because I’m certain I didn’t see everything.
Final Thoughts on Florence
Florence is not an easy city. It’s crowded. It’s intense.
But it’s also one of those places you have to see at least once in your life.
Final Thoughts – Why Tuscany Stays With You
After writing this article, I found myself going back to that trip.
I remembered the rolling hills of Tuscany.
The sunsets with a glass of wine or prosecco in hand.
The quiet mornings with a croissant and an espresso.
I remembered the cobbled streets. The fog slowly covering the valleys. The small Lancia Ypsilon we rented. The gelato. The simple moments.
And all of it together.
There are millions of places to see in the world.
But some places have something different.
Something that makes you want to come back… even before discovering something new.
And Tuscany is definitely one of those places.
FAQ
Is Tuscany worth visiting?
Yes. Tuscany is one of the most beautiful regions in Italy, combining medieval towns, rolling hills and unique landscapes like Val d’Orcia.
Do you need a car in Tuscany?
Yes. Renting a car is highly recommended because many of the best places are in the countryside and not easily accessible by public transport.
How many days do you need for Tuscany?
Ideally 7 to 10 days to cover Pisa, Lucca, San Gimignano, Val d’Orcia, Siena and Florence without rushing.
Is San Gimignano too touristy?
It can be busy, but it’s still worth visiting. The key is to spend more time there and not just rush through it.
Is Spello worth visiting?
Absolutely. Spello is one of the most beautiful villages in Italy and a perfect addition to a Tuscany itinerary, even as a day trip.
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