Puglia

No, that would be shortchanging drastically some on your list especially Polignano a Mare, Lecce.. Where is Lecce on your list, a must see? We spent ten days in Polignano a Mare.
The only place we didn’t care for was Matera but that isn’t in Puglia, rather located in Bascilata. One day was more than enough for us there.
Lecce needs two nights. Otranto and Locorotundo one night is ok or a full day. Trani is very interesting too.
A half day is enough for Alberobello.

Where are you planning multiple day overnights? Up front I will say I have not been to Puglia, but I have been reading a lot about it on-line for months and through this forum since I will be there for two weeks next May (the whole month of May in Italy). Lecce seems a good base if you’re just driving to different cities each day at the tip, and another location farther north for your other locations. Of your locations mentioned, I’m staying at Alberobello, Locorotondo, Martina Franca, Polignano a Mare and Lecce, but I like being in different cities to enjoy their ambiance in the evenings. I will be staying in a trullo at two of those cities.

Half a day? That is enough to walk around. Briefly. Have a meal. Leave. If that is enough for you for a visit, that is fine. Part of your day will be spent parking and leaving parking. Not too mention the drives between.
You count Matera as two days, but it is really one night bracketed by days when you arrive and leave.
This is your 5th trip to Italy, so you have some reference. I assume you have been to Rome, so how long did you spend there?

I'm not clear on your plan, are you going to have a base somewhere and then drive each day to these towns? Or visit two a day and stay overnite at the 2nd one? Or something else?

In any event, a half-day in the places you listed is about all you are going to be able to do unless you want to be walking around empty towns. Like much of rural Italy, shops and churches in Puglia close for the afternoon around 1pm and don't reopen until 4pm or even later. Restaurants serving lunch will be open until about 2pm. As one blog I read said

Sure, it can get a little frustrating when you want to be productive in the afternoon, but instead of fighting it, go with it. Do your sight-seeing in the morning and save the afternoon for beach time, have an extra scoop of gelato for your afternoon treat to tide you over til your late dinner and generally do what the locals do!
https://www.alongdustyroads.com/posts/useful-tips-puglia-italy

We spent about a week in Puglia back in September and visited several of the towns on your list and thought they were very enjoyable. We particularly liked Otranto and Lecce. But the afternoon siesta was something to see! We'd arrive in a place like Monopoli and it was bustling, sidewalks filled, but leaving after lunch it was like "where did everyone go?"

We stayed in Martina Franca and did day trips to most of the towns you mentioned using public transportation, and a half day was enough. I didn’t care for Lecce, however, I understand it is much more attractive at night. We stayed two nights in Matera, but one would have been enough.

My input would be to make sure you take some time in whatever itinerary you
come up to either stay, dine, or do both at a masseria or two along the way.

Since they are usually out in the country, it will be a break from the cities you
visit, usually very peaceful, delicious food & wine, you can walk or bike in the
area.

I’m taking my small sketchbook to do a few sketches in each town, if possible, during the afternoon time John mentioned when places are closed and it’s quieter. Also, should be a good chance to obtain some photos without people in them.

Oh yes, on one trip we rented bikes and rode out through the olive orchards and that was lovely.

Thanks so much for all of your input. It is giving me food for thought. Plan to fly into Brindisi and stay in a town in the area or in between Lecce, Galliopli and Otranto and do day trips to those and then head north and find a base to see the first 6 towns I mentioned doing day trips as well. Matera will be an overnight and then fly out of Bari. I tend to overload the itinerary and don't always get to see everything in the amount of time Ive allotted on our past Europe trips. I don't have a good read on how much time I need in each place but I have looked at the driving distances between them so have planned an acceptable route I think.
Quieter towns in the country for bases would be perfect. Thanks again for your help.

I strongly suggest that you hire a private guide for Matera. There are ancient churches carved into the sassi, which a guide will help you to find and understand. You might find it illuminating to read “Christ Stopped at Eboli,” a memoir by Carlo Levi. In it he recounts the years he spent in a village near Matera, where he was exiled for anti-fascist activity. His account of the extraordinary poverty endured by the people there is good background for comprehending what you see.

Your choice of towns in Puglia is excellent. In Matera, there are many choices for guides so be careful. Some told us that the caves across the Sassi are forbidden to tourists but that simply was not true. There are a set of steps that lead down to the bottom and a suspension bridge to cross the creek/river. From that point on there are several paths to follow up to the caves. All free! It's at least a moderate strenuous hike, but well worth the exertion. We did it on our own. Have fun.

Hi Phyllis,
Our TR below may have some useful bits for you.
Good luck on your trip.
https://community.ricksteves.com/travel-forum/trip-reports/trip-report-bella-puglia-plus-basilicata-and-rome

Polignano A mare, Monopoli, Ostuni, Alberobello, Locotrondo, Martina Franca:
You could base in one of these and visit the others from there - perhaps Monopoli or Polignano if you like to be near the sea.Some people base in Alberobello so they can see it first thing in the morning and late evening without the tourists. Put them in order of which you are attracted to most and stay as long as you need in each. There's nothing worse than getting back home and not remembering which was which if you try to see too much.....
Lecce, Otranto and Gallipoli:
A half day in Gallipoli is enough. The pretty part is the historical centre and that's very small and surprisingly crowded with day trippers.
https://slowtravelitalyspain.blogspot.com/2023/11/puglia-in-september-2023-gallipoli.html
You could stop in Galatina the other half of the day - less touristy and very nice if you like churches and frescoes:
https://slowtravelitalyspain.blogspot.com/2023/11/puglia-in-september-2023-galatina-and.html

Would reccomand Monopoli... Bari also, around 8 in the evening when the whole town goes out for passegiata, nonnas, children, strolling up /down in Sparano..

Such good tips! Grazie amici! Buon Natalie!