The Cutest Small Cities in Southern Italy

Italy family trip! Italy family trip! People call us crazy because we actually enjoy spending time with our extended family… maybe we are crazy but we had the best time! My family took a week to celebrate my grandma’s 80th birthday, rented a 15 person passenger van, hired a driver and a guide, and the 13 of us packed in and drove from the eastern coast of Italy all the way across southern Italy ending on the western Amalfi coast stopping at some of the cutest and coolest cities along the way! The amazingly cute cities that we stopped through were Alberobello, Lecce, Ostuni, Bari, Trani, and Martina Franca on the east coast in Puglia then headed west to stop in Matera, before heading north west to the Amalfi Coast and checking out Sorrento, Pompeii, Positano, Ravello & Capri!

Day 1 – Alberobello

We landed at the airport in Bari to meet our guide Angela before quickly dropping our bags at the Park Hotel San Michele in Martina Franca (which is beautiful by the way!). We headed straight to an afternoon visit of Alberobello, Puglia’s adorable town famous for its “trulli” and an UNESCO World Heritage Site. The trulli were beautiful and we learned about how people who didn’t have much money would build them as housing in order to avoid paying taxes. People would build them and whenever the tax collectors came, they would knock them down! Then when it was safe again, they’d build them right back up. Talk about not being too attached to where you live! After viewing them a look out point across the road, we headed up the steep hill to get a closer look. We even ate dinner at La Locanda del Gallo which is a restaurant inside of an actual trulli! It was our first pasta feast of the trip and it did not disappoint. We started literally every meal with burrata, because how could you not it was always so fresh and fantastic, and this particular meal seeing as it was our first we also had pizza as an appetizer as well. When it finally came time for the main course, PASTA, we were already half way full but it was the most amazing homemade orrechiete (little ear shaped pasta that is typical to south eastern Italy) with tomato sauce and fresh AF ricotta that we scarfed it all down anyways. The food was amazing and sitting to have dinner inside of a trulli was trulli incredible. 😉 

Day 2 Morning – Lecce

Started out the day with a guided city tour of the cute old city of Lecce which is named after the milk from the She Wolf who is the symbol of the town. Lecce also used to be a town full of brothels and if you are looking for it, you can see phallic or penis shapes in many of the windows. These symbols were all quite subtle though and the only one that we saw was because the guide pointed out the iron window bars outside that were in the shape of a penis. She also told us the story of how the owner is forced to keep it there for historical significance against his wishes. Yikes! The town is more noticeably built with local limestone and a lot of pretty baroque style architecture.

The day we were there in June, they were having a moped club meeting and the streets were packed with people and their mopeds of all colors! We enjoyed walking around during the tour but the best was really our delicious lunch outdoors in the courtyard where i had fresh squeezed OJ with my orrechiete pasta! Yes, I did eat orrechiete for lunch and dinner multiple days in a row… whatever it was the local food and let me tell you it was incredible. After lunch, the moms, my grandparents and my uncle decided that they wanted to go SHOPPING! We headed out although that day was quite packed with plans and we really only had time to go into one store (especially with the amount of time the moms could spend in one store…) before we had to head back. My mom found some really cute metallic strappy flat sandals and nana got a small red leather crossbody bag that was just big enough for her phone and a few credit cards when the three of us decided to head out to meet everyone.

We got distracted by outdoor tables and vendors looking at interesting things they were selling and missed a turn or two and somehow ended up outside of the walls of the main old city and had to walk quite a bit longer outside of the downtown area on a major road to meet back up with the family. When we finally got there the dads and kids were like omg there you are, where the F have you guys been?! How did you get lost in the smallest town ever that literally has a wall to keep you inside in the right place and you somehow ended up outside of that wall?? LOL We were a solid 30 mins late and the other moms, Pop-Pop and my uncle still weren’t back yet! When the others finally showed up 15 minutes later, we found out that they stayed in the store picking out belts and having them custom fit for the aunts. Hey, if a leather studded belt is going to be custom fit for you and you need to wait while they cut it and put it together for you, how can you say no?! So we headed back to the bus where Silvio was waiting to whisk us off to the next adorable small Italian town.

Day 2 Afternoon – Ostuni

In the afternoon we arrived at Ostuni where we faced some extreme uphill terrain (really it was just a handful of stairs and a road that was on an incline but with the grandparents it could be a lot). The good news was that they could always make it! And the great news was that once we got to the main square in Ostuni, there was an auto rickshaw waiting to drive them up to the top of the town where there was an awesome lookout point and of course, a church! As they took off in their auto rickshaw, we started walking up the cute streets that had shop after shop of amazing clothes, sunglasses, jewelry, etc. It was hard not to stop at any of the stores on our walk up but either way even just the window shopping and walking up the windy incline road was lovely. When we finally made it to the top, we headed for the lookout point first before venturing into the church. The lookout gave us views of the Adriatic Sea with a ton of greenery between where we were and the water. It was beautiful and we took a full fam photo before heading over to check out the church. When we headed back down the slope to the main square,  it was the perfect time for GELATO! It was delicioussss and we ate while chilling out in the main sqaure. 

Day 3 – Polignano a Mare, Trani & Bari

Quick stop by at Polignano a Mare to look at the view of the beach from the rocks on our way to Trani. We didn’t spend much time here because we only had so much time but it looked beautiful and would definitely be an awesome place to spend the day chilling at the beach!

We also visited Trani which is known for its iconic seafront Cathedral where we saw a couple coming out after getting married! We perused around the beautiful streets, looked out at the amazing water and sat down for a leisurely lunch looking out at the port. Seeing as it was on the sea, I decided it was time to have some seafood (although hello I can’t give up on pasta completely!) so I chose a seafood risotto which had the freshest seafood ever. After a nice leisurely lunch, we headed out.

It had already been a pretty eventful day so we were a bit tired when we arrived in Bari which is the capital of Puglia. We visited the old town center and Cathedral of St Nicola. The streets in Bari were so windy and intertwined! It would have been easy to get lost there without a guide. Our guide also took us by some streets where the women were sitting outside making fresh pasta! It was so cool and crazy to see them making the orrechiete which is famous to the area. Seeing as it had become my favorite thing I’d eaten the whole time we were in southern Italy, I was pretty pumped to see women literally making it by hand on the adorable Italian streets outside of their homes. So cool!

Day 3 Evening – Martina Franca

Although we’d been staying at the Park Hotel San Michele in Martina Franca since we arrived, we had only been using it as a launching off point to head to the other cities during the day. So on our last night, we decided to explore Martina Franca which was such a beautiful little town! It had an amazing massive church in the middle of a square surrounded by tons of skinny side streets with adorable little shops, gelaterias and restaurants. Right off the square where the church was, we ate at an amazing restaurant with tall ceilings, good wine and even better pasta. As if we hadn’t stuffed ourselves with food, we decided we needed gelato that night too and took over the entire gelateria with our family tasting each others gelato flavors as we walked back to the hotel.

Day 4 – Matera

We hopped into our passenger van with luggage in tow to do one of our first longer drives to change hotels. Seeing as we were now migrating west, it wouldn’t make sense to keep our home base in Martina Franca anymore. Listening to music and chatting while we looked out the windows and watched the southern Italian landscape pass by, we drove the two hours until we reached Matera and hopped out when we arrived in the Sassi. Sassi, which is Italian for the “stones” is a really cool historical town that has been a UNESCO World Heritage Site since 1993. It was built into the mountains back in the day because people found caves that were formed out of the stones and they went ahead and carved them a bit further to increase the space in the caves so they could live in them. 

They say that it used to be considered “shameful” to live in the Sassi because of the poor living conditions. People used to have their livestock live in the caves with them because they were so valuable. It was also extremely humid and would get very cold inside of the caves so people would keep the animal excrements in the caves to absorb the humidity and help to heat the cave. There was also no running water so they would regularly dump their waste down the sides of the cliff. Their only source of drinking water was collecting rain. Unfortunately, because of those living conditions, mortality rates for babies were about 50%.

After years and years of living this way, a famous writer – Carlo Levi – visited Matera and wrote all about the people living in the Sassi. This brought a lot of publicity to the town and a few years later the Italian Prime Minister came to visit in 1950 and saw the horrible conditions. This quickly lead the government to pass a law requiring everyone living in the Sassi to be relocated to nearby housing in the surrounding areas. The new buildings had significantly better living conditions.

It wasn’t until many years later in the 1980s that young people who were interested in architecture and artists curious about the caves began to explore and try to restore the Sassi. Archaeologists started to arrive so then by 1993 it was declared a UNESCO World Heritage Site and cave hotels started to open along with people who were interested in moving back into the caves. The rule was that in order to move back into the caves or open a hotel there, the cave needed to be renovated to add in pipes for clean water, toilettes, etc. without ruining the integrity of the caves and being sure to follow direction from conservation experts.

We learned all of the above from our amazing tour guide whose grandmother had grown up in the Sassi where her family had lived for generations. It was so interesting to hear her talk about how her grandmother used to be so embarrassed of living in the Sassi at first but now she feels pride for it being a part of her past and her family history.

After learning everything about the caves, we were so excited to head back to the Hotel Sextantio Le Grotte della Civita to check in and see our cave hotel rooms! It was amazing. They left the physical cave structures exactly as they were and just added your typical amenities into the room like a bed, bathtub, toilet but left the cool old stone sink structures the way they were originally created. Every single hotel room is different seeing as none of the cave shapes were the same. Luckily, we were traveling with 13 people and got to see 6 different cave room layouts! 

Once everyone was settling into their rooms, I took a nice warm bath to relax after the sweaty day of walking around in the heat. I got dressed and headed outside on what I suppose you could call a stone terrace to take in the incredible view sitting around a picnic table drinking wine and chatting. It was golden hour as we spent some nice family time before walking down to the restaurant for another amazing dinner.


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