Originally Posted by bilboburgler

Lecce old town is a nice warren of stone structures with a few large plaza including Roman ruins. A nice vibe and in May not buried in tourists. Like most Puglian places the surrounding sprawl can be not so nice, but Lecce has managed to actually have a pleasant modern city round it. Train links work and the long distance coach station works as well.

Bari and Brindisi are the other two big places I might look at but are more transient places and I'd not stay there for a month. Taranto has an ancient island that is Gritty like Naples while the modern town is shiny and a bit meh.

There are smaller towns which are attractive, again with lovely pearls inside a oyster of modern uck, I've been to most of them except those in the deep south. What are your thoughts?

Originally Posted by HappyTrvlr

We combined Puglia( ten days) with Sicily( 2 and a half weeks). We flew Bari to Palermo on Volotea which saved a lot of time and hassles.

Originally Posted by joan

Just back from 8 days Puglia and 12 days Sicily. We are beach people also.
We loved Cefalu, it is a "real" town with historic center, train access to Palermo, and a great beach scene. We day tripped for a food tour in Palermo. Wish we could have stayed longer than the three nights we allotted for that town. We also stayed in Scicli, which is about 30 minutes from the beach. Another "real" town - what I mean is that it's both historic yet full of every day life. The beach there was not as enticing, but we only spent one day exploring the beaches, since there were so many nearby villages to check out.
Puglia was beautiful, vast, think cliffs and beaches and historic areas. Very little English spoken. But that didn't stop anyone from trying to communicate, especially the shop keepers, they were so helpful and kind.
If I had to choose (what a delicious decision!) I'd choose Sicily, with half Cefalu and half Scicli. The air bnb we stayed in Scicli was amazing, very affordable and full of homey touches.
You will have a car, yes?

Originally Posted by HappyTrails2

Hi Kaybee. I thought I’d weigh in on a couple of the previous suggestions. I need to mention we’re happy just relaxing without the need to be doing some sort of specific activity every day. We’re content wandering around with no specific plan or purpose, stopping for a snack or beverage when something catches our eye. For us, staying in one location for a month requires an apartment, I would be climbing the walls if I were confined to a hotel. Eating out every day would flatten our wallets and fatten our waistlines, so cooking in the apartment, even if it involves some prepared foods, is a must. For all my suggestions, staying in the old city is the way to go, it’s too hectic and less attractive in the newer, bigger and more modern part of any of these cities.

Sicily would make my short list. We spent February 2017 in Palermo and thoroughly enjoyed it. We took a handful of day trips to nearby areas by train or bus. We were lucky with good weather, and from a quick glance online it looks like May is usually quite pleasant.

Another top choice for us would be Bologna, for the city itself and for the proximity to other area towns worth exploring by train. The food is wonderful, much of it inexpensive, and the city has a great feel. We spent two weeks there in 2018 and it was on our list of possibilities for September 2022 but didn’t make the final cut.

You said you’ve been to Rome, but if you’d consider returning, it’s another good choice. We spent March of 2017 there (right after Palermo), and it was one of the more active choices for us simply because there really is so much to see and do. Most days we had a destination in mind rather than just wandering, and we practically wore out the soles of our shoes walking here and there. Rome is my favorite city in Europe, we’ve been there a number of times, always staying in Trastevere not far from the river.

Last month we were in Modena, which we chose because of the location, the weather and because of a language school I wanted to attend. My husband held down the fort running the daily errands and such while I attended class, so we didn’t get bored, but if it weren’t for the school I think a month there would have been too long.

Right now we’re in the middle of a month in Alba, it’s truffle season. There are lots of food and wine centric towns a short drive away, and the weekends are absolutely crazy with crowds and activities during the truffle fair. That would not be true in May. It’s a pretty laid back, small old city area so I’d only recommend Alba if you would enjoy driving to the neighboring towns. You can get to some by train, but I think a car is essential here. We’ve been here twice before, two weeks each time.