Southern Italy- 3 days in Puglia & Basilicata Region

if you are there only 3 days and one day is devoted to Matera, you won't have time for much else. Maybe on the way from/to Matera you could swing by Alberobello and Locorotondo (literally: "Round Place"), both of which are amazing.
Lecce itself has nothing to do with Milan or even Florence. It's much smaller than either (less than 100,000 people). It's an ancient Roman city (older than both Florence or Milan), so they have some Roman sites to see (the amphitheater is famous) and some other nice things. It's a pretty town that is worth visiting and will keep you busy for at least half day. Another trip that would be worthwhile, if you have the time, is to Otranto, a little farther to the South. That area has some of the most clear sea water in the Mediterranean and amazing beaches. Otranto itself is very pretty ancient Greek and Roman city. It's very famous for its fortress, the Castello Aragonese.
Vieste in the Gargano is beautiful but it is too far of the way for you, given your very limited time. Save it for the next time, I'm sure you'll go back to Puglia, it's beautiful. Why don't you Google Images the places I told you and see what you'd like best to visit?

Thank you very much, Roberto.
I appreciate your advice. I did look up Otranto and it does look stunning. With that being said, it looks like we should fly into Brindisi rather than Bari. We can focus on the Lecce/Otranto area for 1 day and then work our way up to Locorontondo/ Martina Franca the next night. It is a lot to cover but this is how my husband and I travel best!
I think we will take the drive along the Adriatic on the way to Otranto and then on the way back up to Locorotondo we will take the “western portion of the heel”. I’m hoping it is as scenic. Any good short stops for brunch along the way?
I am very intrigued by your description of Lecce. I hope we enjoy it as much as all of the other larger towns in Italy we have traveled to. To be honest, my husband’s father was from Naples and his mother from Palermo. We visited both of these southern cities. Although I am very glad we did and I appreciate them, we were somewhat intimidated by the crowded and fast paced life. Perhaps, a bit overwhelmed. More so than say…Rome, Venice, Taormina, Verona, CT, Tuscany, any Amalfi town etc. I know Italian towns/cities are all very unique but perhaps you can describe Lecce’s similarities to another Italian city?
Thanks again!

If you have a car, Ostuni is a beautiful hilltown in the area, near Martina Franca and Locorotondo.

Yes we will have a car....so our options are endless :) Thanks, I will look that up!

We loved Martina Franca, lunching there one day. We also lunched in Santa Maria di Leuca, the very bottom of the heel. It's very uncrowded, the food is fabulous and it is inexpensive. Here's a report on our trip last May. It may give you some ideas.

Thank you. I did read your blog and found it so insightful- it's exactly what I wanted to find. It's hard to get a real feel for the area and this helped.