We hit the road as soon as we finished breakfast to explore the heart of Tuscany – the picturesque rolling hills. We took the scenic Tuscany road – SR2 from Siena to Pienza where we’ll be staying for 3 nights. The first stop was the famous cypresses of San Quirico. Unexpectedly, just after we got out of Siena, we saw this field and hill of sunflowers! We pulled into the unpaved road to take some photos.

Isn’t this beautiful? I have seen sunflower fields in Provence and nothing like this one plus without any tourists except us!

We got out of the car and start taking photos, I was super happy for the surprise find.

Continued onto the cypresses of San Quirico, based on the coordinate I found online, the GPS lead us to the unpaved road…

And ended up to a private road which we don’t want to trespass private property so this was as close as we get to those cypress trees.

We turned back to SR2 and should’ve used Google Maps’ location – type in “Cipressi di San Quirico d’Orcia”. Right on SR2, there’s a small pull out area where it can fit probably 2-3 cars. From there, we walked down to get to the cypress trees; the grasses were super dry and hard to walk on! This was the first time I missed my sneakers at home!

I thought this location was just okay, not sure why it’s one of the most photographed spots in Tuscany. Next, we plugged into the GPS to “Podere Belvedere”. Once again, it is located on a private road that we couldn’t get into further! And look at those poles! I think the only way you can get the postcard-perfect picture is either trespassing or have a telephoto lens to zoom in from here:

We tried to at different angles and they are just not looking like the pics online.

We hopped back to our car and tried another location: Chapel Vitaleta. This one was easier to find and not on a private road, finally! On the way, after we turned off SR2 onto an unpaved road, there are a few beautiful spots worth stopping for. We hardly see another car so we stopped whenever we saw something pretty without any difficulty finding a spot to park, I am surprised at how few people we came across; I thought Tuscany is quite popular among photographers.

I really like the “wave” pattern of this harvested field.

From here, you can see Pienza on the back left of the photo – see some houses and a tower on top of that hill?

The endless rolling hills of Tuscany, it was so peaceful and the heat wasn’t too bad 😀

This field with a small forest in the middle:

We thought those patterns are unique and interesting:

What a huge truck, its wheels are as big as Jason!

A little pond that I wonder if it’s manmade to collect rain water?

The famous Tuscany church – Chapel Vitaleta and I was quite surprised that there’s a farmhouse (private property) right next to it. When I looked at pictures, it gave me a feeling of the middle of nowhere but that’s not the case in reality.

We saw the most people at this location than any other photo location! Those people are not even photographers, rather, some were picnicking there LOL.

A lone tree far away:

Continued onto SR2 to Pienza and we arrived at our hotel – Hotel Residence San Gregorio where we stayed 3 nights for $370. The reasons I chose this hotel were it’s right in Pienza which is a great base for day trips and it has its own free private parking lot. However, its parking lot is located on the back of the hotel but to get there you need to keep driving past the hotel and there’s a small entrance sign that you can easily miss! In order to get in, you’ll need your room key which means we have to check in first so we have to turn back to the hotel, sigh! The challenge is there’s only one parking spot in front of the hotel for unloading luggage and someone parked there already. The other guest who occupied that spot took a very long time OMG that we waited over 10 minutes for them to leave by keep driving back and forth since the hotel is on the main road and no room to pull over!

After the check-in, we walked to the town center for lunch – L’Osteria Baccus; less than 5 minutes walk. Unfortunately, they were fully booked urg! We went to the closeby – Trattoria La Buca delle Fate instead and even it is very busy. I was surprised at how busy the restaurants are given we didn’t come across many tourists. We got a table but it took more than 10 minutes for the waitress to clean up the table and then another 15 minutes to order. I was starving by then grrrr!

We ordered the homemade pasta with the region’s famous wild boar sauce but I couldn’t taste any different than other meat sauce. I wasn’t impressed at all, the totally unfilling lunch with slow service was €22.

After lunch, we made the 45 minutes drive to the nearest Hertz car rental at Chiusi Scalo to replace our car; we got an email that there’s a recall in our car so we need to return the car as soon as possible. When we arrived at the location, it was closed urg even though the hours posted outside the door said it should be open. We waited a few minutes and a guy came, phew! I showed him the email and he said (thankfully his English was okay) he has no automatic car available!!! I asked can he check the nearest location with an automatic car? He said you can try the location in Siena, that’s the best chance. Urm…can you call to confirm they have one before we drive another 1+ hour to get there? He called but no one answer oh yikes! Then, he said, he has an automatic car at the shop so he’ll call to check when that’s ready. With good news, he said the car will be ready in 20 minutes or so and rather we want to wait. Of course, we rather wait! We ended up getting a bigger SUV, a higher class than the one we had, it was more comfortable and better acceleration and suspension system which helped on unpaved bumpy roads!

Well that car exchange took most of our afternoon and on our way back, I chose the “backroad” via SP18 to get back to Pienza from the bottom of the hill up to the town. It was more scenic where we made a few stops for photos.

The road to Pienza where it sits on the top of the hill.

We got back to the hotel late in the afternoon and to rest. Our room was decent in size, of course not luxurious by any means but comfortable.

The stand-in shower door design was awkward to close to make sure no water spill out.

When dinner time came, most restaurants open at 7 PM, we walked out to scout the location for sunset after dinner. This lookout area gave a good view of the rolling hills and fields underneath Pienza.

We dined at Trattoria Latte di Luna for its suckling pig and roasted duck. We were lucky to get a table as we arrived right when it opens, it was almost fully booked.

I was craving for soup so I ordered a soup as an appetizer, it was a little bit salty and I wish they have more vegetables.

Jason ordered the suckling pig, the meat was tender but the skin wasn’t as crispy as we thought. The taste was okay; we much preferred the Cantonese style roasted pig.

My roasted duck was disappointing too, it got saltier the more I ate! The portions as you can see were three pieces so not filling at all! We already missed the Chinese food in Siena 🙁

Dinner cost €41 and I was still hungry sigh! After dinner, we quickly headed toward the lookout for sunset photos. We walked through the small town and I took a few quick snaps of Pienza.

The fields turned into golden color as the sun setting.

The trees and house roofs were blocking the view so we moved around to find an open spot but not much luck.

We continued to walk along the way hoping to find a better spot…the golden sunray lit up the houses to make good pictures.

A beautiful mailbox!

More trees and electric poles blocking the view….

We walked almost all the way to the end of the town and no luck in finding an open spot. It was a beautiful sunset, I wish we drove to somewhere else but it was too late by then 🙁 We’ll try our luck again tomorrow! Life and travel are similar that there are things that we can plan and can’t predict, sometimes no matter how good we planned, it required some luck to make it happen so don’t get upset 😉