Getting from Alberobello from Otranto

It looks like about five hours by bus/train. I've done this trip, it's not terrible. You could rent a car and cut it to 2+ hours, or try to arrange for a private driver, but that could be pricey.

In theory, it could be done in five hours all with local trains (Ferrovie del Sud Est) changing in Maglie, Zollino, Lecce and Martina Franca. Timetable at https://www.fseonline.it/ricerca.aspx (use a near date as they show timetables only for the next week - you will have to segment the trip as Otranto-Lecce and Lecce-Alberobello). Ferrovie Sud Est runs a large network of slow and relatively infrequent commuter trains, not really geared for tourism, and both Otranto and Alberobello are on their network.

Another alternative would be Otranto-Maglie-Zollino-Lecce-Bari-Alberobello; probably it would take the same time, you would need tickets from two different railway networks (Lecce-Bari would be on Trenitalia).

Short of driving, I do not know another way to do it. BTW, I would probably drive. We are talking about using a lot of slow trains going from sleepy town to sleepy town. If you are an adventurous kind of person you may try - the worst it can happen to you is being stranded two hours in a whitewashed station building in the middle of olive orchards. You will be slowly moving between places like this where the last English speaker was seen in 20th century: http://www.yogainsalento.com/wp-content/uploads/2012/11/dove-siamo-3.jpg

If you need fast and easy service, it is not a trip for you.

The worst that can happen is that the train stops fall like dominoes because one is running late (happened to me while trying to get to Matera, with five connections). Fortunately, the barista at the bus/train station knew someone who could drive me the last leg of that trip.

Another idea: Can you spend a night in Lecce and break up the trip?

I'm spending 5 days in Leece before Otranto, so another night in Leece probably isn't possible. Thank you for all the advice. I'll keep my fingers crossed that it all goes flawlessly. I've never driven in Europe. I always rely on Public Transport, and yes, it can make life difficult sometimes. Like when there was one bus a day to a place you wanted to go for a day trip, and it is at 5:00 in the morning, and no return :-) That happened in Sicily. lol.

Thinking again about it, consider also going from Otranto to Lecce and vv. by bus. In summer there should be additional bus service - this would spare you two changes; also buses leave from the Otranto port, in the middle of town, while the railway station is a bit out of town.

Also remember that Ferrovie Sud Est have no Sunday train service.

Last year I spent several extra days in Lecce precisely because the tourist office was arranging van-trips to neighboring towns. There were both half-day and full-day trips offered. The longer trips were only 55 euros. All were transportation-only; the driver would point you to the main local sight or two and tell you when to be back at the van. Printing town maps ahead of time would be a smart move.

Trips require a certain number of people to sign up, so some flexibility as to date and destination is required. For the full-day trips the minimum number of towns visited was four. I hit Alberobello and Matera for sure, and I think also Otranto, in addition to Locorotondo, Gallipoli and others. I took three of the trips.

I consider those van trips one of the best deals I've ever found in Europe. Stop in at the tourist office first thing to let them know of your interest. It would help to have a phone to check status daily, but I just stopped in at the most convenient of the two tourist offices.

Thank you Acraven, Zoe and Lachera for the advice and suggestions. I really appreciate it. I'm very excited about the trip!

I had a couple of 5:50 bus rides in Italy, also encountered the one-bus-at-noon-no-return situation. You roll with it.

Have a great time in Puglia!