We woud like to have a base of operations in S. Italy to explore that region and also want to visit a greek island or two? Where would one recommend staying - Citywise- that is beachy, allows for exploring the boot and also ferrying to Greece? Planning to stay 2-3 weeks.
Sorry I can't be of help but we are thinking of doing something similar next spring and would enjoy hearing about your experience when you return. Thanks Ron
Can't really help from direct experience in southern Italy, but know that the main Italian port cities from which ferries go to Greece are Bari and Brindisi as well as Ancona but that is further north. That should at least give you a starting point to the area you should be looking at.
The southernmost Italian cities from which you can ferry to Greece are Brindisi (the most southern) and Bari. But the only Greek island they will get you to is Corfu.
Just to get your thinking started, the ferries from southern Itlay to Greece run from either Bari or Brindisi (I've used neither) and the trip is rather long. The only Greek island of consequence in the area is Corfu in the Ionian Sea; most people thin of the 'Greek islands' as being those in the Agean Sea. For a city, I like Lecce (but many people don't); the closest beaches are to the east at San Cataldo, but they're small and rather isolated rather than behing busy and fun. Good luck.
Don't overlook Sicily! The eastern coast is closest to the mainland. You can fly into Catania, but I recommend using Siracusa as a base. Was walking among the Greek ruins in Agrigento this past September. Sicily is still a good buy.
Terri, pick up a Lonely Planet guidebook and do some reading about "S Italy". Remember that there are three distinct areas; the toe (Calabria ) the instep (Basilicata) and the heel; "Puglia". We have done S Puglia, and absolutly loved it. There was no "beach town" that we discovered,(with the exception of the small town of Otranto) but there were lots of beaches in certain areas. We loved the seaside port at Trani, the college town of Lecce (a mini Siena) and our drives to al the surrounding sites: Matera, Gallopoli, etc. The food and wine in Puglia are not to be missed. I would spend no more than a week here. You could extend your time by exploring the Gargano peninsula, and by staying somewhere in Calabria. Your best bet to get to Greece is to take a lo-cost inter EU airline flight. The NY Times did a great article on Puglia a couple of years ago: http://travel.nytimes.com/2007/05/06/travel/06Puglia.html?pagewanted=1&ei=5124&en=7fc0ee4c82bf1ba5&ex=1336276800&partner=permalink&exprod=permalink