Edward, there are several Habanos stores in Puglia - the official Habanos website has a Buy-Smoke section with an interactive map of locations around the world. The Habanos Point store in Fasano called Tabaccheria DiBari Vitoantonio is run by some very nice people and has a good selection - I've been there a few times and the owner has been very helpful to a newcomer like me. There is also one in Carovigno called Habanos Cafe Bar with a smaller selection, but also run by nice people, and some in Lecce as well. There are also Habanos Specialist stores in Bari and Taranto. Cigar prices in Italy are regulated by the government - you can find the official price list online - so prices should be the same anywhere you go.
Have fun - Puglia is one of the gems of Italy, but shhh - that's just between us, don't tell anyone.