Husband is 74, I am 65. Both very active, but not big hikers. Are Greek American. Heading to Sicily from May 19-June 11 and then to Puglia from June 11-June 26th. Looking for recs. Will be renting a car. Love history, art, food and off-the-beaten path areas where we can immerse ourselves in the local culture. Want a few guided tours, as recommended. Only want to pack and unpack 4-5 times in each region. Also, best way to move from Sicily to Puglia? Rent a car in each place? Ferry the car with us?
If you are Greek American, and you like history, you might enjoy visiting Siracusa/Ortigia, which were formerly part of Magna Graecia, and the home of notable ancient Greeks like Archimedes. The ruins of Neapolis outside of Siracusa are rather impressive and great to visit and we really enjoyed the old town of Ortigia.
In addition, be sure to visit (or ideally stay for a couple of nights) in Agrigento, on the southern side of Sicily. The Greek temples there are in better shape of any Greek ruins in Greece. There’s a strip running the length of the temples, so you can visit however many you choose, and it’s not completely flat, but it’s paved, so it’s not a hike or difficult walk. We haven’t taken any guided tours in Sicily.
Also, the Villa Romana del Casale in Piazza Armarena on Sicily is a must-see, for the stunning mosaics in a very wealthy Ancient Roman’s palace.
On our first time to Sicily, we did rent from Europcar at the Palermo airport, and took it on the car ferry at Messina to the mainland, eventually returning it at Sorrento. You’d want to verify one-way car rental extra charges to see if you didn’t want to do two separate rentals. Driving all the way to Puglia would involve time for passing through (or seeing) other regions in Italy before you reach Puglia. If so, consider a stop at Castrovillari, in Calabria, on your way.
We did stay in Lecce, Puglia this past fall, and are going back this year. The TI (tourist information office) on the Piazza del Duomo, the plaza outside the cathedral, did a worthwhile walking tour in the late afternoon. We booked it two days before the actual tour, because they didn’t do it every day in the fall - not sure how frequently the tours happen in June.
The best way to go from Puglia to Sicily is by plane, as public ground transportation takes too long.
You can also drive, but for example from Bari to Villa San Giovanni in Calabria, where you catch the ferry, it is 6 hour drive (mostly on freeways). So it’s up to you. Obviously if you fly you need two separate car rentals.
A car is good to have in both regions, however it is not really needed in both Bari and especially Palermo (where it is actually a hassle to have, just like in Athens). So I guess while you visit the two cities, you can keep it parked at the hotel or local garage.
Siracusa/Ortigia area, Taormina/Giardini area, are good bases for Eastern Sicily.
In Western Sicily, you may want to stay in or near Palermo, further west look into Scopello, Castellammare, Trapani areas. Agrigento area is also a popular base for the Valley of the Temples and the Staircase of the Turks (a famous beach). Villa Romana del Casale is near Piazza Armerina, a quaint town. It’s in the interior so it is reachable for a day trip but some prefer to stay a night or two.
In Puglia, since you are there at beach time, I suggest a nase in the Gargano Peninsula (Vieste), one in Central Puglia, like Monopoli or Polignano, from which you can visit a bunch of places (Alberobello, Locorotondo, Ostuni, Martina Franca). Then further south a good base is Otranto, from which you can visit Lecce, unless you want to spend a couple of nights in Lecce as well. Gallipoli is also nearby easily visitable from either. The city of Matera, is not far from Puglia, and you can stay a night or two there, but it is also reachable from any town of Central Puglia in about 1.5 hr drive or less.
Sicily is amazing. On April 10 I posted in the Trip Reports section for the Travel Forum a lengthy report on our visit to Palermo. It was titled Underrated Palermo: history, churches, markets, and the Mafia. it included a couple of tours we thoroughly enjoyed, a lodging recommendation, and some restaurants.