Bari

Visited all those towns during 10 days last fall and here are my thoughts.

Bari is the big port city with the largest population of more than 300,000. So, after arriving by ferry into Bari, we departed for the nearby seaside town of Polignano a Mare. Polignano’s historic center is a joy because it is pedestrianized, photogenic and has great restaurants and really friendly locals. We stayed three nights in Polignano a Mare and actually found street parking for the rental car just outside our apartment.

Monopoli is only about 5 miles by train from Polignano a Mare which made it an easy daytrip destination. Monopoli also has an interesting historic center— but because Monopoli is much larger than Polignano a Mare— getting to the seaside centro storico is about a 30-minute walk from Monopoli’s train station.

Lecce is the great baroque town that makes a good base if traveling through Puglia by train. There’s a Roman amphitheater here, along with layers of historic architecture. In 2001, Luciano Faggiano, the owner of a house in the center of Lecce, was trying to repair what he thought was a broken pipe under his house. While digging under his house, he discovered cisterns, secret tunnels and signs the site during the previous 2,000 years had been inhabited by members of the Messapi tribe, Romans, Jews, and even the Knights Templar! Today, the house of the Faggiano family is open to the public as the Faggiano Museum. It is simply fascinating to visit this unique museum in Lecce.

The historic old town of Ostuni sits on a hill and, from a distance, looks like it cannot be real.

With a car, we were able to quickly hop to Otranto, Gallipoli, Ceglie Messipica and other locations. The little houses that look like hobbits must live in them —trullis— are ubiquitous in the countryside especially around Locorotondo and Ostuni. Guidebooks will tell you Alberobello is the place to see trullis without mentioning you can see them in so many other locations. As a result, Alberobello is overrun with traffic jams and hordes of tourists descending on it. Go to Locotorondo instead. From Locotorondo’s historic hilltop, you can see tons of trullis without the hassle of wading through the throngs in Alberobello.

Have a great trip!

I think it helps to sketch out these basics first: car or not, town/village or rural stay (masseria), one base or two (for your time frame) and what activities do you enjoy doing? Are you entering and exiting via Bari?
One you have that outline, it is easier to choose bases, as you can break Puglia roughly into zones: Gargano (somewhat isolated, beach/nature), central coast and Itria valley (the trulli, charming villages and farmland, beaches), and Salento (beaches and the gem of Lecce)
I always start with an accommodation search on Booking.com with all of my preferred characteristics (parking, terrace with view, etc).