My husband and I recently returned from a two-week trip to Puglia. The RS forum and community was really helpful to me while planning our trip, so I am hoping the info I share will be useful to others!
Short version: it was great! Food, weather, and scenery were fabulous, renting a car was fine. English wasn’t as widely spoken as it is in major tourist destinations, but we managed just fine (neither of us speak Italian).
We flew in Brindisi, rented a car at the airport, and flew out of Bari. We rented a car from Avis, but used AutoEurope to book it. We had no problems with either company. We did elect ALL the insurance (zero deductible) for peace of mind. We also studied/printed out major road signs in Italian, which came in handy.
Lecce
Our first stop was in Lecce, which we loved. We stayed at Palazzo deli Dondoli, which was right outside the old quarter with free (and plentiful) street parking. (Trust me - if you rent a car, parking will become something you think about a lot!) We had amazing gelato at Natale, great cocktails at Quanto Basta, and a truly excellent (yet casual) meal at La Bottega del Corso - a wine bar/cheese shop that also sells gourmet foods.
Otranto
We spent three days at the Hotel Palazzo Papaleo, which was awesome. We parked in the free public lot near the port, which was about a 10 minute walk from the hotel. Otranto definitely had more of a beach town/tourist feel (compared to Lecce). We had excellent meals at Patronale and Arbo Vitae. Beaches we found were rocky on shore and in the water, so water shoes were good. We really enjoyed swimming at the Cala dell’Acquaviva grotto near Castro.
Manduria
We spent two days at the Vinilia Wine Resort - it was a huge treat! This was our “rest day” when we didn’t get in the car at all, just spent the day reading by the pool and biking around the area. We were on the fence about eating at the hotel’s Michelin star restaurant (my husband rolls his eyes at “fancy” food) but we decided to do it the first night because we didn’t want to drive anywhere. It was so good, we ate there a second time! Not our “usual scene” but it was a splurge and totally worth it. The breakfasts there were among the best I’ve ever had.
Matera
We drove to Matera for 2 nights, where we stayed at La Casa di Lucio. Walking around the sassis was interesting and atmospheric, although it was definitely much more crowded with tourists than the other places we visited. (Although to be fair, we didn’t leave the old/touristy area.) We did have really good pizza at Piu Sud. We paid in advance for parking in a lot that was 20 euros per night. We didn’t take an organized walking tour, although I wish we had. Definitely read “Christ Stopped at Eboli” if you’re going to Matera!
Bari
We dropped off our rental car to the downtown location (not the airport) and spent two days in Bari before flying home. Bari was a great “second city” experience. There were definitely tourists, but most people on the street were Italian, lots of students, young families, old people walking dogs. A big mix of old and new everywhere, very vibrant. We stayed at Hotel Boston, which I recommend. We really enjoyed walking around the city. We took the Bari Free Walking Tour (which was worthwhile), had the assassin’s pasta, stood in line for focaccia at Bakery Santa Rita (good but not worth the wait), and excellent gelato at Gentile.
Villages along the way
Places we visited as day-trips were: Galatina, Castro, Tricase, Ostuni, Manduria, Oria, and Altamura. They were all cute and fun to explore, but highlights were Ostuni, Altamura, and Castro. My advice to anyone exploring the region is just to stop at places that make sense for your schedule/route and don’t worry about which is “best” or trying to see them all. You will enjoy whichever ones you end up at!
Puglia was less about “must see” sights and more about enjoying the food, wine, weather, and gorgeous blue water. We loved it!