The millions thousands hundreds tens of long-time readers of Andy’s Travel Blog know that I do some breakneck trips, what my friend Tippe Morlan would call “binge traveling”.  When I have a long weekend off work, I’m usually on the road.

And so it came to pass that I found myself on a flight to Milan last weekend.  I had booked it very last minute, taking advantage of a great offseason international fare from DFW over to Italia (I paid less than $500 roundtrip).

Originally I had designs on heading back to Cinque Terre to revisit one of my favorite photo spots in the world (where I took this picture), but I encountered some weird emotions when I remembered back to my trip there in 2016: it was one of those places that felt too romantic to be at alone.  I decided to forego Cinque Terre, I’ll head back there with a girlfriend/wife sometime in the future.

So, where did I end up?  Somewhere else that is too romantic to be at alone!


Car rental rates were super cheap ($40/day) so I picked up some sort of Kia situation which had wheels on it and set my sights south from Milan.  The autostrade were not very busy so I made good time down to the Tuscany region.

“Where in Tuscany should I go?” I thought to myself as I pulled over at an authentic Italian coffee place for some caffeine (confession: it was a McDonald’s).  The photographer in me knew that Val d’Orcia was a beautiful area with lots of photography opportunities there, so I put it into the search bar of and booked a night at the highest rated place they had, which turned out to be just outside of Pienza.

As I drove into the hills of Tuscany, I put on my favorite Dream Theater song (called The Count of Tuscany, coincidentally) and took in some of the scenery.  There was a light layer of haze as I pulled into the hills around Florence, but my first few glimpses of wineries and Tuscan villas were a wonderful overture for what lie ahead.

a foggy landscape with houses and trees

I made my way further south as the haze was burned off by the midday sun.  Suddenly, the hills became alive with the Sound of Music beautiful colors of green an amber, the sign of the impending Spring season.  I approached the lovely village of Pienza, which made for a formidable yet welcoming view from the surrounding road.

a road with trees and buildings in the background

Everywhere I looked there were cypress trees jutting out of the landscape, it was simply one of the most beautiful areas I had ever seen!

I booked a room for a night at Agriturismo Il Macchione based purely on the high ratings from  Waze took me to the entrance and I was floored.  It was like I was looking at a dictionary entry for Tuscany, it was stunning!

a road with trees on it

The villa was just beautiful, with a few different types of rooms surrounded by idyllic scenery.

a stone building with tables and chairs

The one thing that surprised me was the size of my room!  I didn’t realize I had booked one of their big apartments and loved the ambiance of the space!

I settled in and took a brief break before heading out to some wonderful photography sights!

Gladiator Road

The Ridley Scott epic Gladiator still holds up today, even after 20 years.  The action, the music, and the scenery always captivated me when I watched that film, and I knew that the ending scene from the film was filmed in Val d’Orcia.  I made the short drive over to the hillside where it was filmed.

(spoiler alert if you haven’t seen the film)

I parked at the small lot (called Parcheggio in the map above) and walked down the private road to The Spot.  The landscape was beautiful in and of itself, but the connection to such an epic movie made it really special.  At the end of the road is another B&B called Agriturismo Terrapille.

a road in a field with trees with Royal Porthcawl Golf Club in the background

I even tried my best to match the color palette from the film, just for effect 🙂

a landscape with trees and hills

The wheat had yet to grow in but I tried my best to find some tall grass and ran my hand through it as I walked.

a grass field with a path and people in the background

Roadside Views

As the sun began to set, the clouds played along nicely to make for what appeared to be a great sunset.  I drove from the parking lot for Gladiator Road around a few bends for another look at Agriturismo Terrapille, where the cypress trees would be set upon the horizon.  The actual spot is along SP18 next to Agriturismo Poderuccio, but looking to the west.

The pictures were absolutely stunning, the sun cast long shadows across the hills and the cypress trees looked perfect on the horizon.

a green rolling hills with trees and a road

A little further down the road was a cypress-lined road to another villa, which was also beautiful.  A car happened to be driving down that road when I snapped my picture, I was going to photoshop it out but I actually think it made the scene pretty nice.

a car driving on a road in a green field

The sun continued to set and I refined my composition for some killer sunset shots.

sun shining through clouds over a field

a green field with trees and a sun in the background

Content with my shots, I tried to make it over to one more iconic location.

Cypress Tree Road

I called this Cypress Tree Road because, well, it’s a road lined by cypress trees.  It was also in Gladiator.  And it’s also in every Instagram influencer’s feed.

I arrived at the road ever so slightly after sunset, which mean the exaggerated shadows had disappeared.  I was a bit forlorn but as golden hour transitioned to twilight it left some subtle pinks in the sky around the road so I felt it was worth shooting anyway.

a row of trees on a dirt road

a row of trees in a field

I made my way back towards Pienza when I noticed the “afterburn” of the sunset was leaving some wonderful colors in the sky so I pulled off at the same spot as earlier for one more picture.

a landscape with hills and trees


I strolled around the village of Pienza, enjoying the quiet streets of the offseason before tourists invade for the summer.

a stone alleyway with lights and buildings

I love doors for some reason, and the warm evening light over this one caught my eye.

a stone building with a door and windows

I made my way back to my apartment at Il Macchione and collapsed from the exhaustion of driving all day.

Podere Belvedere

Jet lag had its way with me and I slept in a little later than I had hoped.  The weather was forecast to be cloudy the next morning, ruining my chances for a good sunrise shot, but I awoke after sunrise to find the sun was still out!  I hurriedly grabbed my photo gear and scampered out to another spot on my list: Podere Belvedere.

(The linked spot in the map above is the actual spot I took these pictures from, not Podere Belvedere itself)

I wanted this picture because I felt it encapsulated so much of what makes Tuscany special.  The light played along very nicely, casting warm tones across the villa and the surrounding hills.

a landscape with hills and trees

a landscape with trees and hills

Even the road I walked down to find my composition was beautiful.

a road lined with trees

Zigzag of Monticchiello

Sufficiently happy with my Belvedere shots, even though I missed the best light, I made my way over to another small village called Monticchiello, where there’s a famous zigzag road lined by, you guessed it, more cypress trees.

(again, the map above is where I took the picture below from, not the road itself)

If I were cooler I would say that this road is to Tuscany what Lombard Street is to San Francisco, the tight turns making for a fun drive and even better photos.

a landscape with trees and hills

When I arrived back at Il Macchione they brought a lovely breakfast up to my room.  I finally relaxed for a few seconds and enjoyed the ambiance.

a table with food on it and a fireplace in the background

I was sad, as my time in Tuscany was quickly drawing to a close.  I needed another place to roam to for the next night, sooooooo…

Side trip to Rome

I had never actually been to Rome, so I drove down south a few hours and made my first visit to the Eternal City.  The Sistine Chapel at the Vatican was absolutely worth dealing with the crowds and the vista of Ponte Sant’Angelo with St. Peter’s Basilica in the background wasn’t the worst thing either!

a bridge over a river with a large building in the background

What a whirlwind!

Talk about a crazy long weekend!  After Rome I drove back to Milan to meet a colleague and her husband for evening drinks, bid them farewell, and flew back to the United States the next morning.

I cannot wait to return to Tuscany again, ideally with a girlfriend/wife, and next time I want to do it better.  I want to leave my camera at home and enjoy some good food and great wine!


Have you been to Tuscany?  What did I miss seeing?  Tell me in the comments below!

Get the latest updates daily!

You have Successfully Subscribed!