Itinerary Advice for Puglia

I think the factors to bear in mind are that Alberobello gets bus tour crowds, so I would try to aim for early morning or late evening. (May should not be too bad though.) Also, note that a lot of places close up from 12-5 or so. This can include museums, so check the hours for anything you especially want to see. In some places, at mid-day through late afternoon, it can feel like a ghost town--at slow times of year, this can include restaurants, so always have a lunch plan (I ate, well actually purchased and then threw in the trash, the worst sandwich of my life in a cafe in Locorotondo). Last, in some towns, the train station is actually located outside of town and too far to comfortably walk--see if your guide book details this info, or check on google maps. You do have all day, but this might be a case where you look into hiring a driver--you'd get to see a lot more of the countryside this way--this was a special part of the Itria Valley to me. An alternative if you have ample time and are physically able, is to walk between some of the towns (or just set off and you can always turn back if a town to town walk is too much)--there are walking paths indicated by brown signs. You walk past farms and the cherry trees should be full of fruit. Check your schedules carefully, and good luck!

ETA, those three villages do have a train station within a 15 minute walk--I believe it is uphill for Locorotondo and definitely for Cisternino.

If you zoom in on Google Maps and examine the scale, you can get a good idea of how large the historic part of each town is; look for the area with a bunch of squiggly little streets, often shaded peach.

I'm odd in that I like to walk every street in the historic district when I visit a small town. If nothing else, it gets me away from the other tourists. There aren't many places so small I can cover them in less than 2 hours. I know I rushed around Alberobello so I wouldn't miss my due time back at the van, but unfortunately I don't remember how long the stop was. If you're using public transportation, your options will probably be extremely limited. Have you checked the schedules? I've often had a choice of something like 1.5 hours or 4.5 hours in a town. And many's the time I skipped lunch to keep the entire day from falling apart. Given a choice, I'd plan between 3 hours and half a day at each stop, figuring that if I had too much time I could linger over lunch.

There's at least one trullo in Alberobello that's open to the public. The entry fee was very low in 2015. Yes, it's touristy, but I still found it interesting. As noted above, you need to check the schedule to be sure you don't run up against a very long afternoon siesta period if there's a sight you want to go inside.

We all have our preferences, but mine would be Alberobello and Locorotondo over Cisternino. I agree that you'll need to study the schedules to work things out. We did Puglia all by public transportation, and planning ahead is key.

Once in Lecce, visit Monopoli and/or Polignano a Mar. We stayed in Polignano the whole time and loved it there. Used it as a base to explore the towns you mention.

I appreciate all of your responses. Thank you. I think I will go to Alberobello first , then on to Locorotondo, and then back to Martina Franca. I think Cisternino might be too far to reach in my day of touring. I wish FSE had some kind of day pass!