Puglia in February

These are the Pugliese villages on the list of the "Most Beautiful Villages in Italy": Alberona, Bovina, Cisternino, Locorotondo, Maruggio, Otranto, Pietramontecorvino, Presicce-Acquarica, Roseto Valfortore, Specchia, Vico del Gargano. I've only been to Otranto and Locorotondo.

Other possibilities (based more on my notes than on personal experience) are Trani (Jewish quarter and important cathedral), Taranto (larger city), Grottaglie (pottery town with ceramics museum), Martina Franca, Castalaneta (recommended by NYTimes but without specifics). I didn't check populations; I don't know how many of those actually fall in the "small town" category.

Trani is not a small town but is beautiful, the cathedral by the sea and all the rest : https://slowtravelitalyspain.blogspot.com/2023/04/why-i-love-trani.html
Also Giovinazzo, Molfetta and Barletta (in that order of preference in my opinion, on the main train line from Bari)
In Valle d'Itria we liked very much Martina Franca
https://slowtravelitalyspain.blogspot.com/2022/08/puglia-in-may-valle-ditria-cisternino.html
Further south, near Lecce, Galatina for the Cathedral and Frescoes (awesome) and, because it's near Lecce a quick stop in Copertino.
I also like Brindisi, not a small town either but the old town is quiet and relaxing for a stroll in low season
https://slowtravelitalyspain.blogspot.com/2019/11/puglia-brindisi-in-november-trip-report.html

Thank you acraven & Tinac.
While I do read the list of the most picturesque places, I also appreciate people’s personal experiences, their advice on local events, art, cuisine, or sightseeing off the beaten path.

I also liked Martina Franca, and Galatea with its astonishing frescos of the Basilica di Santa Caterina D’Alessandria – I returned there for a second visit. Cisternino and Locorotondo were a favorite over Ostuni, the latter being quite touristy, of all the whitewashed villages.
Trani and Barletta have always been on my radar, but I keep missing them in each trip. Would you recommend I stay overnight in Trani, since it’s almost as big of a city as Lecce?

I was planning a night in Bari and catching the train the following morning to the northern towns.

One of our other posters spend 4 nights in Trani and enjoyed it; I haven't been there myself. I'd consider what sights were of interest (I know only about the cathedral, the Jewish quarter and the rest of the historic center), whether there are any other worthwhile stops in the area that might make good day trips, and the travel time from Lecce.

The tourist hearts of Trani and Bari (the old town) are not that big in relation to the entire town. We spent a few nites in Trani a couple of years ago and used it as a base. It was a delight to walk thru the old town, to walk by the park during the passeggiata and seeing the locals talking animatedly on the benches, and to dine along the harbor.

Trani has a ' historical town by the sea' feel to it, more than a city feel. It makes a good base for visiting the other towns along the coast

I enjoy strolling the streets of Lecce's historical center also - plenty of cafes, where you can relax for a few and "watch" La Dolce Vita of the locals.

A good idea maybe to spend a weekend in Trani and/or one in Bari and use them as a base to visit other towns?
Any suggestions for Barletta, anyone has been there?

I've been to Barletta a couple of times, not as much to see as in Trani or Bari. But the castle area is nice, also Basilica del Santo Sepolcro which is in the centre just behind the mysterious Colosso. Maybe a half day trip by train...
https://slowtravelitalyspain.blogspot.com/2019/10/puglia-in-september-barletta.html

Piggybacking a little bit on the OP's question:

I've been wanting to go to this region, but due to a variety of factors (time/travel companions) the usual suspects keep winning out. Would the OP find nice weather in these coastal beach areas in February? I was thinking of perhaps going in June instead, but could swing February depending on the answers

If you want to spend time on the beach as in sunbathing then you should keep to June. February could be ok for walking and sightseeing. But the wind from the north can be cool on the east coast in Puglia too. Weather is unpredictable but check out the averages for an indication. I went end of March one year. Nice when the sun was out but coolish in the shade or when windy...(for what it's worth - anyway definitely not lying on the beach weather

I enjoyed reading "Slowtravelitalyspain". I will definitely use it as guide for Trani, Barletta etc. Really nice pictures also. Thank you for sharing the link.

Last year I stayed in Lecce for a few weeks during the month of March. The weather was really nice, low to mid 70's during the day which allowed for short sleeves. But I would not consider it warm enough to drive to a nearby beach for a swim.