Polinano A Mare : **** nice scenery, good restaurants, easy to walk around, friendly small town feeling. We chose this as our base and were very happy with it. Very comfortable feeing. Many little shops with friendly locals. The old town in on a peninsula of sorts with cliffs dropping to the water. There is one main beach between two cliffs which is a good photo ops. Its a great place to get an apartment and buy some local fish at very low prices.
Bari : **** a bigger town but lively, and vibrant. A lot of shopping. good castle. good restaurants. Seaside : so-so. This would be a good base with its large trainstation and amble restaurants and shopping. There are also ferry connections to Greece, Croatia, and Turkey. And high speed train to Caserta outside of Naples. Its a fun place with many coffee shops and lively crowds.
Monopoli : ** So, so seaside resort. Nice "city wall" near water with swimming outside the wall. Somewhat nice interior old city. Not too many restaurants. The city itself has more shops and city feel than nearby Polignano a Mare (5 minutes north on the train)
Lecce : ** Fairly boring unremarkable place with 2 buildings with pretty interesting facades, and an interesting doorway (port) on the city wall. Otherwise, you feel like a rat wandering a maze of big old buildings. A few restaurants but we only saw one that looked pretty decent. Its pretty far down (1:20 from Bari) and almost no one speaks English, nor are there English menus. The tourist industry looked kind of primitive.
Alberobello : **** Really cute neighborhood with hundreds of restored Trullis. There is a kind of a Cotswold, Hobbit feel. Many Trullis are converted too shops or homes. Clean and nice. Good photos.
Matera : **. developed tourist sector, view of hillside of an old ghetto with some wrecks and some refurbished apartments. Famous caves are closed to the public and 2 miles away. Its not particularly an easy place to get to, and while fun for what it is, I would not go to any effort to ever return.
Cisternina :: * hilltop town with small old city, and nice park with view overlooking valley, a few good restaurants with good prices
Locotorondo : * hilltop town with small old city, and nice park with view overlooking valley (nicer than Cisternina)
Ostuni ("the white city") : ** slightly better and bigger than Cisternina Locotorondo, but similar white marble streets. This town is a little more developed. Spiral road up to church at top, with a view looking down at the seacoast a few miles away (pretty unremarkable). All restaurants seem to feature hot dogs, hamburgers and coco cola.
Marina de Ostune : ** a few miles from Ostuni is a mini-Monopoli. In October, only 2 out of a dozen restaurants were open. One smallish castle-like structure near sea. Otherwise boring.
If I was to return to Puglia , I would go to Polignano a Mare, Bari, and Alberobello. However, there is not a strong pull to return.