Three weeks in Southern Italy. Must-sees? Must-do's?

I would split your three weeks, half in Sicilia, half in the other southern regions (Campania, Basilicata, Puglia). A car will be a great help.

Mainland: Napoli, Sorrento, Paestum, Amalfi Coast and Ravello, Matera, Bari, Lecce, a couple of nights for daytrips to the Puglia "white towns". On the way to Sicilia, Tropea.

Sicilia: Taormina, Cefalu, Palermo and Monreale, Trapani and Erice and Segesta, Agrigento, Piazza Armerina and Villa Romana del Casale, Siracusa.

You will have to choose among these, you won't have time for all. You could easily spend all your time in either Sicilia or Southern Italy, since you seem to return (3 previous trips).

Definitely agree with Zoe. 10-11 days in each should be plenty of time to get the vibe of each area, and their differences as well, of which there are many. You'll find the cuisines of Campania and eastern Sicily, for example, are miles apart, and both fantastic.

Zoe--have you ever done the train/ferry deal from Villa San Giovanni in Calabria to Messina in Sicily, or vice versa? I imagine you'd have to have some time to burn, but if I ever get over there for an extended period of time, that traverse is on my bucket list!

Jay, I have done the ferry crossing many times, last time was part of a trip from Napoli to Palermo when Terminal 3 burned down at FCO (couldn't get a flight out or a hotel room). The crossing itself takes about 20 minutes. Loading the train cars (!) onto the ferry and off again - along with all the other vehicles - takes at least an hour. I plan to do this again when my last mainland stop is in Calabria; otherwise I find it more convenient to fly.

I once took the ferry from Milazzo Marittima to Lipari, the ticket was about 4euro.

I'd tend to drop Puglia/Matera on this trip to spend more time in the Amalfi area and on Sicily. If you want to squeeze in Puglia/Matera, I would choose either Capri or Ischia since visiting both would chew up two days. There's definitely no time for Corsica or Sardinia with Sicily in the mix.

If you're flying home from Palermo, try to fly into Catania; that should slightly reduce the driving you need to do. A car will be extremely helpful in Sicily. It's awkward to get to, so you probably won't return there often and will want to see as much as possible this year. It's borderline insane to drive in Palermo, so try to schedule things so you can visit Monreale (a must--the best sight in the area) before settling into the city, then drop the car before the rest of your Palermo time. Do some reading about the many religious buildings in Palermo. Their architecture is quite varied and I enjoyed seeing many of them, though I am not all a religious person. Some people are ready to leave after one full day in Palermo (it's crowded, hectic, not particularly lovely); those interested in the churches and oratorios might want three days.

For me, the Baroque cities inland from Siracusa (Ragusa, Noto, Modica, etc.) are a must. Ragusa's the one for the overnight stay.

Consider saving Puglia and Basilicata (also eliminating Corsica and Sardinia from consideration)--as fond as I am of them! I would plan on close to two weeks on Sicily, with the remainder spend in the Naples/Amalfi Coast area. That will still be tight, even though three weeks is such a luxury--there is just a tremendous amount to see. Depending on the ultimate travel logistics, you could drive down the coast to get off the beaten path (unless this trip was in August of course). You may end up deciding to be very targeted in your Sicily explorations to give the AC more time.
Ischia has thermal spas, and Paestum would be added to my must-list.
Since you are already flying out of Palermo, I will not go into other alternative (saving Sicily to instead do a heel-toe road trip).

Thank you all so much for your suggestions! If anyone else wants to chime in, please feel free! I will actively be planning this trip this month (January).

For going to and from Sicily, flying is usually the best way; even if you're driving one way, you'll want to fly the other.

Although Palermo is a larger city, Catania has a larger airport with more flight options. Going into one and out of the other is the best way to see more of the island without backtracking.

To find all options, use Skyscanner: http://www.skyscanner.com/. Many of the flights to Sicily are on budget carriers, so be sure to go the airline's website to do a dummy booking (up to the point where you put in your credit card) to learn all the rules and fees.

Because of the stricter baggage rules on budget airlines, it can be cheaper to fly Alitalia, which includes one free checked bag and has a more generous carry-on allowance. To get the best prices for Alitalia domestic flights, use the International website which has an English language option and the same prices as the Italian website (only in Italian): https://www.alitalia.com/en_en/. The US site has MUCH higher prices - for the exact same flights.

All of these flights will be cheaper the sooner you book; the prices only go up. So, book them as soon as you're sure of your plans.

I did a report on my Sicily trip from April-May of 2014, and although it was therefore a few years ago, you should get some ideas from it: https://community.ricksteves.com/travel-forum/trip-reports/sicily-palermo-caltanisetta-siracusa-taormina

Based on your suggestions, I've decided to start my planning with Sicily and work backward from there. I think I'll allot at least a week in Sicily, if not 10 days. Like I said, we already have tickets to fly home from Palermo.

We usually prefer to stay in one place for at least 2 or 3 nights and use it as a "base" to visit other places (we will have a car). In our younger days, we were fine with going from town to town each night, but now that we're older (in our mid-50s and each use CPAP machines), it gets cumbersome to keep packing and unpacking each night.

That said, I was thinking of perhaps using the area near Catania as one base to see the Eastern coast (Syracuse, Mt. Etna, Taormina), and then the area near Palermo as a second base to see the Northern coast (Palermo, Cefalu, Monreale, Segesta). I'm not sure what to do about Agrigento (I don't think I can miss the ruins there)! Google Maps says that it's a ~ 2 hour drive to get there from Catania, so maybe that could be a day trip, or spend one night there on the way to another place (????)

What do you guys think?

I would stay in Siracusa rather than Catania, but That's because I love Ortigia (oldest part of Siracusa).

Cefalu is a great stopover but can be a daytrip from Palermo (an hour by train, less if you drive). Don't miss Segesta, you will never forget seeing it from the highway as you approach the temple. There is a shuttle that will take you to the theatre and other ruins.

Agrigento, with a car, can be a very long daytrip from Palermo. The ruins are extensive; drink lots of water on the paths. You will see a special breed of goats that live on the archeological site.

I, too, would prefer to base in Siracusa rather than Catania. In addition to a large historic district, Siracusa has a good archaeological museum and a nice arch. park, plus it's a more convenient gateway to the Baroque cities in the interior. It would be a shame to go all the way to Sicily and just bounce around the coast.

I wonder whether Agrigento could be handled as a stop on a repositioning drive from Siracusa to Palermo. The diversion adds at least two hours to the drive, and I would be concerned about the possibility of luggage theft from the car, however.

This is sounding like a really nice trip. Looking at logistics, then perhaps something like...

Fly in to Rome. Train to Bari - 5 nights in Puglia
Train to Naples - 5 nights on Amalfi Coast
Fly from Naples to Catania
Taormina (3) > Syracuse (3) > Agrigento (2) > Palermo (3)
Fly out of Palermo

With respect to David's proposed schedule, I have a thought:

If you need to go into the city of Catania to pick up transportation to Taormina (airport's on the other side of Catania), you might consider checking your bags at the Catania train station (there was a checkroom in 2015) and seeing Catania's historic district before moving up to Taormina. It's not a terribly long walk from the station to the area around the cathedral. With a morning arrival, a visit to one of the markets would be worthwhile. I can't vouch for the taxi situation (prevalence or absence of overcharging, I mean) in Catania, because I never used taxis there.

I used taxis in Catania, they were fine.

I like Davids itinerary, but would take the one hour flight to Bari instead of the six hour train ride.
Both Alitalia ( better baggage allowances) and Ryanair have many flights a day and you're already at the airport. Just remember to allow at least two hours between landing and check in.

I had been under the impression that we were flying in to Rome, but my husband just told me that I'm mistaken. The only flights he booked already are from our home in California to London (to visit our cousins for a few days), and flying home at the very end from Palermo. But in between, inside Italy, we haven't bought the flights yet. We still want to see the Naples area and Pulgia, though!

Skyscanner shows that there are direct flights from London to Naples (not to Bari), so it makes sense to fly in to Naples, see that area for about a week and then fly or drive to Bari to see Puglia for about week.

The big questions are getting to Bari and Sicily. It looks like it's only about 4 hours to drive from Sorrento to Bari. So, driving to Bari from Sorrento would be do-able. From there, do you think it would make more sense to fly to Catania in Sicily, instead of driving down? The tour books make it sound like there isn't really much to see in Calabria, so maybe it's worth a miss, in exchange for a few more days in Sicily. What do you guys think?

Volotea flies Bari to Catania direct, but not daily.

Fly from London to Naples for 5 nights on Amalfi Coast
Train to Bari and hire car for 5 nights in Puglia
Fly from Bari to Catania (check Volotea for direct flights)
Taormina (3) > Syracuse (3) > Agrigento (2) > Palermo (3)
Fly out of Palermo

Thank you! Yes, that's pretty much what I had in mind, except for taking the train to Bari. Is there a reason why driving there isn't a good idea?

No, that's a personal choice for you to make. I haven't driven in Italy myself.
Maybe pick up a car in Salerno and check out Paestum before driving to Puglia.

If you can squeeze a night in Matera, it's between Napoli and Bari.

I'm trying to figure out where to stay in the Naples area from a logistics perspective.

To explore the Naples area, Rick Steves suggests using Sorrento as a base. But the map shows that it will take an hour and a half each way to get to Naples city from Sorrento, and if we want to see it over the course of a couple of days (seems to me that it will take about 2 days to see the best sites in the city of Naples), an hour and a half drive twice each day to and from Sorrento would be a real drag. Pompeii is also closer to Naples than it is to Sorrento.

I'm wondering whether it would make more sense to stay just outside of Naples for a few nights (to see Naples city, Pompeii and Herculaneum), and then drive down to Sorrento and stay there for a few nights (to see Sorrento, Paestum, Capri, and Ischia).

I'm also wondering how to handle the Amalfi Coast. I have also seen on Rick's video that driving on the Amalfi Coast can be challenging, and that it might be better to go on a bus tour of it instead. However, I have also read that it's so pretty, it's worth staying somewhere along the way for a night, perhaps Positano. Well, you can't do both! It seems to me that you'd either do a bus tour of the coast, OR drive it and stay in Positano. Or maybe drive to Positano, stay there overnight and do a bus tour to see the rest of the coast? It's confusing to try to figure out the best approach!

After seeing the Amalfi Coast and Paestum, we plan to drive to Bari and see Puglia for about a week.

I appreciate your insight. Planning this trip has been more confusing than usual. We usually like to stay in one place for 3 to 4 nights and use it as a base.

You've pretty much outlined all of your options. Let us know what you decide. lol

How many days do you have to work with for this segment? I would stay IN Naples to see Naples (as well as Herculaneum and Pompeii, either of which you could alternatively see en route to the Amalfi Coast). And to see the Amalfi coast, stay ON the Amalfi coast. I'd rather enjoy the places themselves 2-3 days each. Sorrento is for people who want to see it all from one place, but that then requires time spent on the commuter train, bus, and ferry. I would not dare deal with traffic and parking, even in early season. You can use ferries and buses to explore around Positano and the islands (though some islands may be more easily reached from Naples--that will in part determine your day allotment). You could also stay on an island in between Naples and the AC. (But that may be more time than I think you have available--you can really spent two weeks in the area and not see it all!) Then I'd pick up the car in Salerno and drive to Paestum.