Tips from Jessica
We flew into Brindi, stayed at Lecce as the base as it is very centrally located. Do rent a car and drive around from town to town.
Lecce hotel = Patria Palace (https://patriapalace.com/en/)
The Patria Palace Hotel Lecce is a five stars luxury hotel in the hearth of the city, just in front of Santa Croce church.
Wine tour with amazing tasting/lunch pairing place = Cantele (http://www.cantelewines.com/puglia/)
Cool towns to visit = Lecce, Gallipoli Porto, Polignano a Mare, Otranto
Grotto restaurant is located in Polignano a Mare (it is touristy, expensive, but good ambiance)
Lots of great little seafood restaurants and bars throughout, very price friendly.
There’s a lot of Jewish inhabitant / heritage sites throughout this region worth checking out.
Beautiful beaches, from flat/sandy to rocky/cliffy.
I’d say 4-5 days would be sufficient if you really want to properly wind down and not rush it.