Road Trip to the Heel of the Boot: Puglia
- Maddy Cummings
- Mar 13, 2019
- 9 min read
Updated: Mar 15, 2019
For this road trip we only got as far south as Torre Dell’Orso but there is certainly so much more to see, both further south and around the tip to the other side of the peninsula to cites such as Gallipoli and Taranto. I decided to do Torre dell’Orso first as it makes more sense to do the bulk of the drive first and work our way back to Bari bit by bit. Here is a map outlining the entire itinerary.

Day 1: Torre Dell’Orso & Lecce
We flew into Bari, the second largest city in southern Italy, which is located in the region of Puglia. To kick off the road trip we rented a car. We had zero idea what to expect for what car we would get, except for the fact that the transmission needed to be automatic. I was not prepared to learn how to drive stick for the first time in Italy! We went through the rental process, forked over an extra 100 or so euros for the young driver charge (unfortunately we were unsuccessful in catfishing them into believing that I was 25) and waited patiently for our car to be washed. Low and behold, a bright red Fiat zipped around the corner and the rental guy handed me the keys, chuckling at our excitement.

The drive from Bari Airport to Torre dell’Orso is about 2 hours and 15 minutes. Along the way you can catch your first glimpses of the Adriatic Sea if you weren’t fortunate enough to have a window seat on the flight over to Bari. We arrived to Torre dell’Orso without a real plan in mind. We wanted to grab a little panino (sandwich) and hit the beach to tan. Unfortunately we grossly overestimated the temperature and sadly with the wind it was too cold for such activities. In fact, most of the locals were dressed in full winter coats and scarves while we flexed our tourist status in our dresses and sleeveless shirts.
We google mapped ourselves to literally “Torre dell’Orso” and it took us to basically the centre of town in front of the main beach (spiaggia). We parked the car on the street nearby and looked around for a good lunch spot. There was an older man picking flowers/picking weeds (could have been either I’m not known for my gardening prowess) in the a centre grassy area and as we passed by him he immediately said “Ciao!” and struck up a conversation entirely in Italian. This was just the beginning of a very Italian linguistic experience. Out of anywhere I have visited in Italy, this was the most immersive into the culture as some of the locals of the small southern Italian towns we visited spoke very little English. I know a little bit of Italian so we chatted a bit and he asked us our names, introducing himself as Fausto and asked where we were from. He was very excited to learn that we were from Canada and asked us to come to his restaurant. We shrugged, why not, and followed him to Ristorante Adriatica, located in the main area of town. We sat down outside on the patio not knowing what to expect and ordered a light lunch. I got what was basically Calamari but with shrimps and octopus as well.

The seafood was so fresh and delicious but Fausto made the experience even better by coming over every 15 or so minutes with a new little snack for us to try. By the end of the lunch (pranzo) he had given us capricolo, burrata, local white wine, olives, these little local biscuits called Tarralli and fresh strawberries. We thanked him profusely for his kindness (grazie mille) and set off to check out the two main sights of Torre dell’Orso: Grotte della Poesia (Cave of Poetry) and Torre Sant’Andrea.
Both are only about 10 minutes in either direction from town. We hit Grotte della Poesia first and the views of just the cliffs and the sea on the walk over to the cave were amazing on their own. We spent so much time admiring them we had to remember we hadn’t even hit the main sight yet. We walked over and were stunned by the beautiful sinkhole. It was actually such a shame that it wasn’t warm enough to swim because I can picture myself jumping into that again and again and baking in the sun on the rock above. This was occasion 1/1000 on this trip that I vowed I would return somewhere in the summer.


We could have spent a lot more time just sitting and admiring the view but it was pretty windy and we were chilly so we ran back to the car to drive over to Torre Sant’Andrea. This was equally as stunning cliff views including the rock towers surrounding the area.

We hopped back in the car and set off to the next destination and where we’d be spending the night: Lecce!

Lecce was only a half hour and was all through beautiful curvy little back roads bordered with the most olive trees I have seen in my life! We got to Lecce around sundown and got settled into our Air B n B after finding free parking on Viale San Nicola. The Air BnB we stayed in was stunning, inexpensive and in the best location- I’ll link it below. You can also rent from the B&B company itself if you want different room configurations!
After a well deserved nap due to our 5 am wake up in Rome, we got ready for our dinner reservation at Osteria da Angiulino. I was so glad I made a dinner reservation because people were lined up at the door hoping to get a table! They somehow heard my name as Carol when I called for the reso (not sure how) because they didn’t have my name down but Carol never showed up. Shoutout Carol! We were the only English speakers in the entire restaurant, the rest of the diners being either locals or Italian tourists. To start, we ordered some potato croquettes (which were delicious) and I decided to take the plunge and sample a local delicacy: cavallo- I’ll let you google translate that one for yourself. I was pretty nervous to try it so I got it in a small meatball form. It was actually delicious! For my main course I got another local specialty: Orchiette. Orchiette are little circular pastas, named for their resemblance to little ears. I got mine with tomato sauce and cheese.

This was one of the cheapest meals I’ve ever had out. We all got appetizers, pasta mains, a litre of red wine and a dessert each and the total for us three was 39€..... UNREAL! On our walk back to the air b n b the streets were buzzing with people huddled around outdoor tables outside bars chatting and having wine and snacks!
Day 2- Lecce, Ostuni & Alberobello
We woke up ready to check out the quaint little yellow-beige town of Lecce. After checking out and dropping our bags at the car, we walked back through the old town gate, Porta san Biagio and into the old town.

We saw some of it at night but in the daylight it was a completely different experience! Each little tiny street leading to the main square, Piazza Sant’Oronzo was prettier than the next.

We made it to the main square and I grabbed a little cornetto (croissant) and we wandered around for a bit before heading to the castle. At the castle we stumbled across a big outdoor market with people selling everything from light bulbs to earrings to high heels for 5€!


We then strolled down through some more modern streets to the Duomo and the square surrounding it.

We were getting a little hungry and wanted to have lunch in our next destination, Ostuni, so we got in the car and drove about an hour to reach the beautiful white city.

To get to the city you pass through another cute little town called Carovigno and suddenly the city of Ostuni, perched on a hill will appear out of nowhere in ahead and you will be just as blown away as we were. We drove up and parked our car just below a really panoramic viewpoint for the city (just off of Corso Vittorio Emanuele) and headed to a little cafe for some panini!

The cafe we went to was called Coffee & More and had the cutest couple as owners. They helped us choose what sandwich to get. I got a prosciutto, buffala and olive spread sandwich in pizza bread. It was delish!
We then set off to climb up to the very top of the hilled city, enjoying wandering through the white side streets, and grabbed some gelato on the way to enjoy at the top. We thought it was going to take much longer to get to the top and we’d make it at sunset but it actually on look like 10 minutes! At the top was a great view of the Adriatic Sea.
We walked back down and got in the car to drive to Alberobello, home to the famous Trulli of the the region.

Trulli are little stone huts that date back to the 16th century that peasants used to live in! Apparently the stone roofs were useful to regulate temperature during the hot summer months.

On the way to Alberobello from Ostuni we could see little smatterings of Trulli popping up here and there and then we knew we had arrived at Alberobello once we were completely surrounded by them! We stayed in a part of the town with over 1000 Trulli. The Trulli have since been renovated and many B&B companies rent them out to tourists- including us!
Tip: when checking into your hotel, make sure one person stays with the car. We parked the car in the first parking lot we found and figured the staff would tell us where to find free parking and we could just move the car so we didn’t bother to pay for the two minutes we’d be parked there. The parking enforcement in Alberobello is ON IT! We came back with one of the staff from our B&B as the parking enforcement agent was finishing our ticket and despite our pleas, the ticket was already processed by the time we got there. 29€ if paid within 5 days.......
We dropped our bags and walked around the Trulli village. We did indeed make it for sunset (much to our IGs’ delight- sorry for the spam guys) and saw the amazing views of the ~golden hour~ light off of the stone roofs. It was honestly such a crazy sight to take in. Then we went back to chill for a while and get ready for our dinner reso.

For dinner we went to il Pinnacolo which was also housed in a Trulli. I had an unreal mushroom papardelle there. Would recommend.
Day 3- Polignano a Mare

In the morning we set off to *gasp* pay the dreaded parking ticket. We were told that you have to pay the ticket in the post office so we went and just in case this happens to you too, which it won’t because you’ll be using my ~protips~, this is what you do.
You go into the post office and go to the kiosk and click the one with the € symbol. A ticket will spit out with a number and then they call your number you go up and fill out your name and address on the slip they have you with the ticket. Then you pay the post people the amount of the ticket and they give you a receipt.
After all that was said and done we got back (picture this next phrase in a Willie Nelson voice) on the road again. Destination: Polignano a Mare.
The drive there was, shocker, gorgeous and only takes about 30 mins. Once we got there we checked out the main vista where all the postcard pics are taken, the incredible cliff side city. This vista is located on Lungomare Domenico Mondugno, but you can’t miss it!

We then hit up La Terrazza for lunch and had some delicious pizza. We then went down to the beach beneath the cliffs: Spiaggia Polignano. There is a small little cave opening you can walk through to sit on the ledge and watch the waves come in. You have to wade through some calf height water which was a bit chilly but well worth the view.
We wandered around the city for the rest of the afternoon, taking in some of the pretty ceramic stores. A lot of it was closed due to it being low season as well as la pausa (nap time) at the time.
Emilie had to catch a flight back from Bari so we bid the coast a sad Arrivederci and headed back to drop her at the airport. We left a huge time cushion just in case we wanted to take a more scenic route and that we did!

All in all, this trip was one of my all-time favourites. Food and lodging were quite inexpensive, especially compared to other trips I had been on- even within Italy. It was also the least touristy experience I have had so far in Italy. Before planning this trip, I was considering doing a road trip down the Amalfi coast, which I have visited a few years prior but I am so glad I decided to do the other side of the coast and see Puglia instead. The people were all so nice and were so willing to help out. They also were extremely patient with my broken Italian and made an effort to help me learn instead of just switching to English right away. I am 100% coming back when it's warmer and taking much longer to be able to relax on the beach and make it to the other side of the peninsula- this time swimming in the Ionian Sea.
Until next time Puglia,
Ciao!
Restaurants & Hotels Along the Way
Day 1:
Torre Dell'Orso
Lunch:
Ristorante Adriatico
Via Chiesa, 3, 73026 Torre Dell' Orso Melendugno, LE, Italy
http://ristoranteadriatico.it
Lecce
Airbnb:
Piazzetta Chiesa Greca
https://www.airbnb.com/rooms/12103776?location=Piazzetta%20Chiesa%20Greca%2C%20Lecce%2C%20Province%20of%20Lecce%2C%20Italy&guests=1&adults=1
Dinner:
Osteria Da Angiulino
Via Principe di Savoia, 24, 73100 Lecce LE, Italy
Day 2:
Ostuni
Lunch:
Coffee & More
Corso Vittorio Emanuele II, 1, 72017 Ostuni BR, Italy
Alberobello
B&B:
Tipico Resort
https://www.booking.com/hotel/it/tipico-b-amp-b.en-gb.html?aid=356980;label=gog235jc-1DCAsocUIOdGlwaWNvLWItYW1wLWJIM1gDaE2IAQGYAQm4AQfIAQ3YAQPoAQGIAgGoAgO4AsnxqOQFwAIB;sid=861306fc8fbc5b24eab2ab57f2e0a531;dist=0&keep_landing=1&sb_price_type=total&type=total&
Dinner:
Il Pinnacolo
Via Monte Nero, 30, 70011 Alberobello BA, Italy
http://ilpinnacolo.it/en/
Day 3:
Polignano a Mare
Lunch:
La Terrazza
Via S. Vito, 1, 70044 Polignano A Mare BA, Italy
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