Puglia Accommodations

There are 4 towns near the locations you plan to visit that you must not miss. They are:
ALBEROBELLO
LOCOROTONDO
OTRANTO
POLIGNANO A MARE

Make sure you include them in your itinerary.

Alberobello and Locorotondo are only 5 minutes from each other by car so you can stay in either or in the vicinity and visit both from there (they are just over one hour east of Matera).

Polignano is less than one hour (maybe 50 min) from Bari airport, but for the night before your morning flight I would prefer to stay closer to the airport. Giovinazzo fits that requirement at only 15 min away from the airport, and would definitely be my choice, if you don’t care to stay in Bari itself.

As far as picking up your car in Naples, if you don’t wish to drive in the city of Naples (who would?) maybe you should pick up the car at the airport.

I would add the extra nights to your existing stops (any of them could use an extra night, though I think Ostuni might be the most "bang for your buck" because of its proximity to the Itria Valley and coastal towns).
Is your flight out super early? You could theoretically drive the hour from Ostuni if not. I have stayed in Bari--the old town is quite nice. I have also stayed in Monopoli before a flight--45 minute drive. And when I had an earlier flight, I stayed in Giovinazzo, just 10 minutes from the airport and a pleasant little place. People seem to like Trani, which is also close.

@valadelphia would LOVE to add another night on to each place, but reservations were a little bit of a puzzle. Mostly been dreaming of staying at this particular Masseria, and their availability was limited. I was thinking about maybe finding another Masseria in the valley for the remaining nights, but a few nights on the coast also seemed like a nice way to try a little bit of everything (city life in Lecce, farm life on the Masseria, and somewhere along the coast). Glad to hear you liked Monopoli- what is it like to have a car there? is it easy enough to find a parking lot to keep a car at? street parking? having to move it often?

Thank you!

We were in Monopoli in late May, and we occasionally had to drive around a bit to find parking (we were staying in old town so had to park outside the town walls), but it was not a big deal, and I would venture a guess that October would be similar. Monopoli is a good base for the coast as well as the Itria Valley. I looked at Polignano too, just went with an apartment in Monopoli and felt there would be more restaurants, etc. The drive to the airport in the morning was fine, but if it has been very early we would have moved closer. good luck!

Ck out Palazzo Maresgallo..Lecce. stayed 6 nights last July..wonderful..spot in middle of Lecce..just amazing refurbished palazzo..fantastic breakfast..walk everywhere.