North to South June 2017

Unless you actually plan to visit the Amalfi Coast again, I would probably plan to fly from Milan to Palermo or Catania in Sicily. I think you have enough time depending of course how long you intend to spend in each area. You could do 2 days in Milan and 5-7 days in the lakes area, then fly to Sicily for however much time you have left. You don't really need a car for the Lakes since you can take a train from Milan to whatever town, on whatever lake, you decide to use as a base, and then use trains and boats to get around to whatever other towns you want to visit on the lake. You could do a couple of bases, maybe one on Lake Como and one on either Lake Garda or Lake Maggiore. Then train back to Milan and fly to Sicily where you probably would want to rent a car as it's easier to get around by car than by public transportation there. You'll hear people say that Sicily deserves a couple of weeks, and I agree, but it's still worth going and you can see quite a bit of the country in 5-7 days if that's all you have.

You may get differing opinions here, but I wouldn't try to hit Milan - lakes - Amalfi Coast - Sicily all on one trip--certainly not on a two-week trip. With a car you'd move around Sicily a lot more efficiently than I did on trains and buses, but I'd still prefer that you have 10-14 days there, and you wouldn't be bored with three weeks on the island. I'd hold off on Sicily if you've got a chance to return to see it on a later trip.

Have you already seen Venice? It would fit nicely with Milan and the lakes before you head south. Other possibilities up in that area include the Dolomites (another area where a car would allow more flexibility of movement, though public transportation can be used), Verona, Padua, Vicenza, Ravenna, Bologna, Ferrara, and quite a number of other cities in Bologna's orbit that I haven't gotten to yet. Someone else was asking about Trieste today, and it was agreed to be a very interesting city as well. You really wouldn't need a car just hopping from city to city in the north or moving from northern to southern Italy without stopping.

If for some reason you don't want to spend all that much time up north, you could combine some northern Italy time with the Amalfi Coast (car probably not helpful) and Puglia/Matera, where a car would be handy. But Puglia, like Sicily, can be pretty hot in June, so you'd need to be prepared for that.

If I've misunderstood your post, you do not actually intend to re-visit the Amalfi Coast on this trip, and you can manage three weeks, you could put together a very interesting combination trip, spending a week or so in northern Italy, then flying to Sicily. But that would mean a fair amount of airport time, which is a dead loss from the sightseeing perspective.

It's up to you but these are the very bare minimum times for each locality in my opinion.
Lake Maggiore: 3-4 nights
Lake Como: 2-3 nights
Lake Garda: 3-4 nights
Venice: 2-3 nights min
Naples area (Amalfi coast, Pompeii, Capri, etc.): 4-5 nights minimum
Sicily: 7-8 nights very minimum (partial visit with a car. For everything in Sicily you probably need at least a couple of weeks).
Since you may have seen the Amalfi Coast already, you may want to skip it and fly from North Italy (Milan? Bergamo? Venice?) all the way to Sicily.

Make your selection. I gave you the full menu.

I agree with previous posts. Fly from Milano to Palermo or Catania, fly from Sicilia from the other.

Sicilia can easily take ten days, a couple of nights in Milano and a couple of nights at one of the Lakes would be my choice.

So glad I found this forum! Thank you so much for all of your knowledgeable suggestions. We didn't think about flying from Milan to Sicily we were planning on taking a "fast" train. I know it will take time out of our itinerary to fly, but it seems like the cheapest and most efficient choice. Is there any specific tour you would suggest in Sicily? Thank you!!

There is, alas, no fast train to Sicily. You can get from Milan to Naples in less than 4-1/2 hours, but from Naples to Palermo takes about twice that long. I tried doing the trip by night train in 2015, and it was a really miserable experience because of the condition of the rails. The train jerked side-to-side constantly, and I don't think I slept for even one moment. Fly!

Pick up a guidebook to Sicily (a non-current one from the library will do for initial decisions about what most interests you) and read about the island. There is a great deal to see, and there are sights all over the island.

Palermo is notable for a large number of churches and oratorios of varied design and décor. There are museums and markets worth visiting, too, but it is a large, noisy, hectic city with traffic that can be intimidating. It wouldn't be my choice for the first stop in Sicily, but that might be the way it works out with your flights. How much time you want to spend there will depend a lot on your tolerance for visiting a bunch of churches. I'm not religious but still saw at least eight or ten and found them very interesting. Do not miss Monreale, which is just outside town. A side-trip to Cefalu (very old former fishing village, now beach town) makes a nice change. Rick commented in one of his videos that he really likes Cefalu, but I found a few hours enough for me since I wasn't looking for beach time and it's fairly small.

Trapani is a small city with an attractive historic district but I think it's mainly visited as a jumping-off point for the unbelievably picturesque Erice, which can be reached by car, bus, or funicular. There are important ancient ruins in Selinunte and Segesta, not too far from Trapani. Another important classic site is Agrigento, in a more isolated location on the southern coast.

Siracusa has a huge medieval district (Ortygia) as well as a nice Greek theatre, archaeological park and archaeological museum. It's my favorite Sicilian city, but some prefer Taormina. It's a good base for the baroque cities in the interior, but you might opt to stay in one of them--probably Ragusa--for a change of pace and see the others (Noto, Modica, Scicli) from there. Definitely don't spend all your time along the coast.

Taormina has one of the world's most gorgeous locations and is a lovely hill town. It gets heavy cruise traffic and sits above a beach, so it's a very popular destination for northern Europeans. Expect it to be full of tourists during day-trip hours. I'm sure it's a different experience early in the morning and in the evening. It's quite close to Mt. Etna and not too far from Catania.

Catania is the second-largest Sicilian city. Less hectic than Palermo and with a pretty historic district around the cathedral, it also has an interesting market. Although I liked it, I think you could just spend your first or last night there (depending on how your flights work out) in order to have time for the many other attractive Sicilian destinations.

In the interior of the island is an important Roman site with fabulous mosaics, the Villa Romana del Casale. It's near Piazza Armerina, which seemed attractive as I buzzed through it in a taxi. There are also some lightly-visited Greek ruins at Morgantina. The nearby cities of Caltagirone (known for ceramics) and Enna are also worth a visit.

What acraven said.

You will actually save time in your itinerary by flying from Milano to Catania or Palermo (the flight is less than two hours, as I recall, plus waiting and security time); you can be in Sicilia in the time it takes you to get into and out of Napoli Centrale.

Here is a great website for Sicily- there are hundreds of links to all kinds of info about Sicily.
I used it a lot when I went....

Best of Sicily