Planning next trip starting in the heel?

You can fly to Bari from either Florence (via Vueling) or Pisa (via Ryanair).
You can fly to Brindisi from Pisa (Ryanair)
There are plenty of option in Puglia (Apulia):
http://www.viaggiareinpuglia.it/hp/en
The city of Matera, although not in Puglia, is also a popular destination in the area.

Hi Charlie. We spent some time in Lecce which is a very nice town, great base for seeing the heel. You can drive all around the heel as a day trip. We passed through lots of charming towns between Lecce and Polignano al Mare where we also stayed: Ostuni, Martina Franca, Alberobello (Trulli houses), Otranto, and then there is the Castle del Monte. The food is terrific and the prices are excellent as well. I understand it is mobbed (beaches) with Italians in August. We went in May and the weather was very nice.

Roberto and Laurel gave you excellent advice. Matera is about one hour from Bari by car, if you want to begin there and go south to Monopoli, then to the heel of the boot, and work your way to Bari if you are flying out from there.

My friends and I did this trip (seeing the places Laurel suggested) with a base in an agriturismo outside of Bari, Podere Papilio.

Recently I met a soldier on the train from Vairano-Caianello to Cassino, and he said his plan is to retire at Lecce. He considered it the best place in Italy to be. This comes from a young man who has been all over Italy and knows it well. So I pass that information to you.

Thank you all for the input. We are hoping to start by the heel and work our way north from there. We would probably try to fly into Bari, maybe stay in Lecce, rent a car, and do day trips in the area. We have never been in this region. Then we plan to drive up to Orvieto and continue north to our other destinations. Can you fly into Bari through Rome? Where is Brindisi? Is it better to fly into there?

Bari is probably a better choice than Brindisi, check flight options.

I would consider seeing Lecce and THEN basing yourself somewhere else for day trips by car. Saves the hassle of driving in a city and finding parking. Staying around Locorotondo gives lots of day trip options.

If you decide to use Lecce as a base, I recommend a b&b, Il Cortile dei Esperidi. It's located a short walk (5 minutes?) from a gate to the historic area. It has its own underground garage. The owners are the kindest, most helpful people I've ever encountered in the hospitality business. The rooms are large and sparkling clean, and the prices are quite reasonable.

Is there any reason to consider the toe instead of the heel? Do you think it would be better or more interesting to rent a car in Rome at the airport and drive to the heel or toe? That way would spend a couple of nights in Rome to recover from the flight from LA. Just thinking.

Is anybody familiar with Soriano Nel Cimino? Our timeshare as a place there and thought we might stay there for a week.