We're planning a month long trip in October, start in Venice with trip down the Adriatic Coast, then over the mountains to Basilicata and Calabria, flying home out of Naples or Rome. We plan a few days ferry trip from Bari to Albania, then back to Italy, continuing on down to Lecce. Rather than constant driving we're thinking of staying in a few villages or towns, and moving South every 3-4 days. We are contemplating radiating day trips so that we aren't constantly on the move. While Lecce, Matera, and Consenza are all on the itinerary, the Venice-to-Bari stretch is unknown territory to me. Any suggestions for interesting towns or areas to poke around in would be terrific.

October is a bit late in the year and may be rainy.
Gems along your itinerary:
Chioggia
Abbazia di Pomposa
Ravenna and Classe
San Marino and San Leo
Urbino
Frasassi Caves
side trip to Umbria
Macerata
Termoli
Tremiti Islands
Vieste Gargano
Castellana Caves

We really enjoyed Ascoli Piceno, it's just a short drive from the coast towards the mountains and is very pretty.

You might consider spending 3-4 days in either Sulmona or Lanciano in Abruzzo province.

Sulmona, known for its candied almonds, has a nice main piazza flanked by a 12th c aqueduct and is the birthplace of Ovid. From Sulmona, we took day trips to the Abbey of San Clemente a Casauria and several towns, including Scanno (on the list of "Most beautiful villages of Italy") and Pacentro.

Lanciano is a beautiful small city with a nice old center and many churches, including Santa Maria Maggiore, which is important architecturally for Abruzzo and has a nice silver cross by Nicola of Guardiagrele. I recommend a day trip to Abbazia di San Giovanni in Venere, a stunning 13th century abbey on the coast near Fossacesia. In another area of Italy, this would be overrun by visitors. But its relative remoteness from the usual tourist routes makes it a peaceful stop.

http://www.sangiovanninvenere.it/

Great suggestions. I've got my giant map out and have begun plotting. Keep them coming!

The above link for sangiovani is a SPAM link

Stunning beautiful town, almost no English speaking tourists. Has all the charm people seek but mercifully no crowds.

https://www.lonelyplanet.com/italy/puglia/vieste

bookmarking

A question about traveling this region: Train between towns and rent a car where we stay every few days? or rent a car in the north and keep with us the whole trip? I have not driven in Italy but I am aware there are special rules for cities.

Difficult question. You could easily do it by train, but with a car you will be able to visit places that would be difficult and time consuming on public transport.

I am familiar with the Riviera Romagnola. In order north / south, my favourite places are:
1) (must) Ravenna (S.Vitale, S.Apollinare in Classe, etc.)
2) (optional) Cesenatico
3) (must) Rimini old town: http://www.emiliaromagnaturismo.com/...an-rimini.html
4) (optional) San Marino
5) (must) San Leo
6) (must) Gradara
7) (optional) Monte San Bartolo - lovely walks and secluded beaches (Fiorenzuola di Focara) between Gabicce and Pesaro

There's a lot more really in the area, like the Archeological Museum in Verucchio, the Malatestiana Library in Cesena, hilltop villages like Montegridolfo and Sant'Agata, but you'll need weeks.

You will get a much better deal to rent a car for the entire time. The driving here is very easy. Just research your routes and parking options for towns like Lecce before hand, and you will be fine.

Thanks to all Fodorites!