We have planned a tentative itinerary for travel at the end of September 2016. We arrive in Rome (from Canada) and plan on spending 3 nights. Then we will take a flight to Bari and spend 4 nights in Puglia. We plan to spend 2 nights in Lecce and another 2 another spot not yet determined in Puglia. We will then drive to Sicily staying 6 nights distributed among Taormina, Siracusa, Agrigento, and Palermo. We will then take the overnight ferry to Naples and spend 3 nights in Naples. Then back to Rome for our flight home.
Here are my questions:
1. When in Puglia where would you suggest we base ourselves for the other two nights?
2. Our one long driving day is from Puglia to Sicily. Is this doable? Will there be a delay in crossing Straits of Messina?
3. We plan to rent a car in Bari and drop it when we arrive in Palermo. Does this make sense?
4. Any suggestions for lodging in Sicily?

Thanks in advance for suggestions and advice. This is our second trip to Italy, the first was 40 years ago and we only visited Venice and Milan. We are very excited to be returning and spending 18 days.

Have you bought your internal-Italy air tickets yet? Because if not, I would suggest pretty much reversing the trip -- land in Rome and go directly to Naples for 3 days, then (ly from Naples airport into Catania, rent a car and tour Sicilyt, and then fly from Palermo to Bari and rent a car, and drive to Matera in Basilicata for 2 nights, then drive to Lecce. Drop off the car in Brindisi and fly to Rome and spend the remainder of your time in Rome.

It is a long and demanding drive from Puglia to Sicily, so I would look to get rid of it. Plus, I am not sure what the situation is with renting a car on the mainland and leaving it Sicily. There might be a drop-off fee.

If you already have purchased an unchangeable air ticket to Bari, then consider going to Lecce first from Bari, then Matera, then drop off the car in Naples airport and either visit Naples first or fly to Sicily . Depending on how you get to Sicily, you can either fly back to the mainland or take the ferry.

I don't know why there would be delays on Straits of Messina other than weather delays. In case you haven't done this already, you should go to the TripAdvisor forum for Sicily and post all of your questions there as well. There are Sicilian natives who post there, and give excellent advice about details for everywhere in Sicily.

I'd think there is more than enough to do in Puglia and Basilicata without hacking over to Sicilia.

Ostuni, Martina Franca, Gravina, Matera, Potenza are all good bases.

There is more than enough to do in Rome without leaving. Likewise Naples. There is more than enough to do in Sicily without going to Puglia.

The point is: That's not the point.

If there are sights you would like to see in Puglia and Sicily and don't mind the travel, then go to Puglia and Sicily. People include more than one region of Italy in their travels all the time and enjoy their trips. The first time I visited Sicily, I combined it with Rome and the Amalfi area. I knew there was plenty to do in all places just to pick one of them, but I wanted to see more than one of them.

For what it's worth, I went to Puglia once (for much longer than you are planning) and disliked it so much I doubt I would ever return, although I have returned to Sicily, Naples and Rome and would return again and again.

bilboburger likes Puglia so much he got married there, and Puglia has many other fans on Fodor's, as does Sicily, as do Naples and Rome. Plenty to do everywhere in Italy. Pick the itinerary that interests you.

Thank you sandralist and bilboburgler! We haven't booked internal flights. The only things we have booked are the flights from Toronto to Rome and home. We have booked our hotels in Rome (can be cancelled) based on the many great suggestions on this site as well as tripadvisor. I'm feeling like Judy in that this research, albeit fun and exciting, can also be confusing and exhausting! My husband, the planner, is now looking at revising his original itinerary perhaps eliminating the long travel day to Sicily. There is so much to see and do but are now feeling that we need to narrow our focus.

What about Rome - Naples - marinobus - Bari (trips to Matera, Castellana Grotte, Alberobello or so) - Lecce - Bari - Volotea flight to Catania or Palermo (frequent buses to Taormina and Siracusa from Catania airport; bus and train from Palermo to Agrigento, Siracusa and Catania) - flight from PMO or CTA to Rome?
There are also overnight ferries from Palermo and Termini Imerese (Cefalu) to Civitavecchia, port of Rome.
http://www.gnv.it/

If you want a feel for Sicilia watch some of the Montalbano or Montalbano Giovane TV series, the scenery is wonderful and is certainly on my list to visit some time. If you like the whole mountain side thing then you might prefer Basilicata to the relatively flat Puglia. Alex Politzi has done some TV series on Italian Islands that also covers Sicily.

It depends if you are ever going to come back. Internal flights are dirt cheap (AlItalia goes bust pretty often, until the next sucker/investor can be found) so there are lots of ways to get around.

This trip sounds very rushed to me -- you are trying to cover in 19 days a set of places that many of us would find hard to see in twice the time, and even then, at a breakneck pace. Are you sure you will actually be able to see the things you want to see?

I recommend that you get some good guidebooks (or spend some time with a few in your local library), identify the things you most want to see in each location, note their opening/closing times, and mark them on a calendar. Then pencil in your transportation, add some time on either side (for getting to/from your lodging, checking in/out, packing/unpacking, getting oriented, etc.) and see how things fit together. That's really the only way to determine whether this itinerary will suit your needs.

The good news is that even if you cut your destination list in half, you will still see some wonderful things!

Sicily is much better than what is shown in Commissario Montalbano movies.

If it was me, I would fly into Rome and head to Naples for 3 nights then Sorrento for 2 nights, Matera for 2 nights then Puglia for 7 nights fly from Bari to Rome and spend the remaining nights in Rome.

I would leave Sicily for it's own 18 day trip.