I live in Bologna and went to Puglia at the end of last year for the first time, loved it!, here are some highlights off the top of my head:
- We stayed a few nights in an _Agroturismo_ near Cisternino that makes olive oil, our room was actually a _Trullo_ [1], a type of building typical of the area. There are many such places.
- If you want to see lots of Trulli in a picturesque town, Alberobello is beautiful but quite touristy. Still worth the visit imo.
- In Cisternino, they have these amazing restaurants (that is, if you eat meat) that are basically butcher shops where you choose the meat you want and they grill it for you. One of the specialties are "bombettes". The town itself is pretty.
- In Martina Franca, you have to try (again meat) "Capocollo di Martina Franca", which is like the Parma ham of the region. You can probably find it throughout Puglia, but the town is nice.
- Ostuni is a very beautiful white washed town.
- Lecce is well worth the visit, I can't really remember all the restaurants we visited, just one for seafood "Il Vico Del Gusto", we liked it a lot.
- Coming from Lecce but you can probably find them in other places in Puglia are the pastries "pasticciotto", which is a shortcrust pastry filled with custard cream, (sometimes they add other ingredients). Yum.
- Another typical dish of the region is the pasta "orecchiette con le cime di rapa", which is this ear-shaped little pasta with broccoli rabe, garlic, chili flakes, olive oil, and sometimes anchovies. Simple but very nice.
- We stayed a few nights in an _Agroturismo_ near Cisternino that makes olive oil, our room was actually a _Trullo_ [1], a type of building typical of the area. There are many such places.
- If you want to see lots of Trulli in a picturesque town, Alberobello is beautiful but quite touristy. Still worth the visit imo.
- In Cisternino, they have these amazing restaurants (that is, if you eat meat) that are basically butcher shops where you choose the meat you want and they grill it for you. One of the specialties are "bombettes". The town itself is pretty.
- In Martina Franca, you have to try (again meat) "Capocollo di Martina Franca", which is like the Parma ham of the region. You can probably find it throughout Puglia, but the town is nice.
- Ostuni is a very beautiful white washed town.
- Lecce is well worth the visit, I can't really remember all the restaurants we visited, just one for seafood "Il Vico Del Gusto", we liked it a lot.
- Coming from Lecce but you can probably find them in other places in Puglia are the pastries "pasticciotto", which is a shortcrust pastry filled with custard cream, (sometimes they add other ingredients). Yum.
- Another typical dish of the region is the pasta "orecchiette con le cime di rapa", which is this ear-shaped little pasta with broccoli rabe, garlic, chili flakes, olive oil, and sometimes anchovies. Simple but very nice.
Hope that helps/convinces you to go!
[1] https://en.wikipedia.org/wiki/Trullo