Thanks Kybourbon and zebec as well as the rest that have weighed in. I now need to narrow down the towns in Tuscany and Umbria that interest us and as recommended find lodging nearby.
​​​​​​I don't at this point have a preference from Bologna to visit Tuscany first, or Umbria. Is renting a car from Bologna and driving to either region the way to go. Or should I train from Bologna to a town farther south then hire a car. I'm fine either way I just don't know what options make the most sense. Assuming I choose Bevegna and near Pienza as base camp.
Also, I am curious what town makes for the fastest train trip from near Pienza or Bevegna to Naples. This was our planned next destination.

Thanks everyone. Happy Memorial Day Weekend
Mike

This is weird. There was a post after my #80 by the OP that I could see and my post #82 was response to it. I had response windows appear above and below the OP's post and finally got my #82 to post. When it did appear, the OP's post was no longer showing. Perhaps it was in some moderation situation and I got trapped in between? I assume the OP's post will appear at #81 at some point.

KyBourbon, thanks again for your input. I will be looking at the towns of each region to figure out which ones stand out for us. Now I have a better plan for which town I want to leave from To head to Naples.

Unless you really like moving around, there's no reason to move so much. We stayed 5 nights in Ortigia and did day trips. Lovely drives through the mountains and little villages. Caltagirone is a place we liked. Most of the pottery you will find in Taormina comes from there and it's cheaper in Caltagirone. Taormina views are great. Wouldn't spend 3 nights there though. We missed Ragusa and Noto, sadly. For sure don't miss the temples in Agrigento, but it's not a great place to stay. I'd stay in Ragusa or somewhere and go for day trip to Agrigento. Loved staying on Ortigia. We did go to Cefalu since that's where my great grand parents are from. It's a cute little town and has one of the 3 cathedrals in Sicily that has beautiful mosaics as in Monreale. There's a little town east of Cefalu that's worth visiting too but I can't remember the name of it. We are planning on going to the west coast next year since we didn't get there last time. Just look at the driving times to places you want to go and pick a place in the middle and maybe not move around so much. but that's just me! Palermo is a very interesting city I'm looking forward to seeing again. and I know it's an add on, but since you have 3 weeks you might consider taking the ferry to Malta. I'd go to Malta over staying in Catania.

Christym907, thanks so much for your comments on Sicily. I have to admit I haven't spent as much time planning on this portion of the trip. I took the advice of several people who mentioned spending 3 weeks to see places or don't go due to the sites and sizes. I also reviewed a guide book or two to get a overview of where to go. I agree on minimizing places to stay and have heard good things about the Siracusa area. I will research further.

On a separate note I have decided to add a nights stay to Naples. I will arrive via train from either Foligno in Umbria or Chuisi in Tuscany for now.
I am interested in visiting Herculaneum, Capri, and Paestum. However, I discovered that Paestum is easier visited via train from Naples and obviously Herculaneum.
I am thinking of visiting Capri from Positano instead of from Naples. Something like this,

Naples 5 nights.Day trip to Paestum, half day for Herculaneum and possibly Mt. Vesuvius
Positano 5 nights with day trip to Capri. Visit Amalfi and soak in the coast.

My last concern is from here I am planning on a short flight to Catania from Naples . Then spend my 3 weeks in Sicily. I would leave Palermo to Rome. Finish our holiday in Rome for 5 nights and then fly to Chicago.

So, plan A I leave Tuscany or Umbria by train and head to Naples. Spend time there , visit Paestum etc. and then car train bus to Positano . I would then have to get back to Naples for a flight to Catania.

Plan B I leave Tuscany or Umbria via train to Naples. I believe I have to then train to Salerno and then bus or ferry to Positano. After my 5 nights here I would then head for Naples. This would allow me to fly to Catania without worrying about getting to Naples from Positano and the airport.

I'm leaning towards plan B. Unless there is an easier way I am not aware of with train travel. Thanks everyone.
On a side note, Marija I just finished reading your stay in Naples. Wonderfully written and my wife was drooling over pizza and pastries. Ciao

Naples/Capri nay be easier than Naples/Positano. Positano is small and if the sea is a bit rough, ferries won't put in there. I do think Naples at the end is better since you have a flight to catch. There is an airport shuttle bus from Naples (at least in non pandemic times - Alibus) and taxis at set rates.

I don't know if the Campania Artecard would be cost effective for your stay in Naples or not, but it probably would if you are willing to do things in a row. It's 32€ for 3 consecutive days which gives you free admission to the first 2 sites you visit (1/2 off after the 1st 2) and transport in Naples (metro/bus), to Ercolano/Herculaneum (Circumvesuviana train from Naples to Ercolano, not the express) and to Paestum (Trenitalia regional train only I think, not the IC or other trains - make sure to check). Herculaneum entry is 11€ and the museum in Naples is about 10€. Paestum is about 6€. There is only a 5 minute or so time difference between the regular Circumvesuviana train and the express between Naples/Ercolano anyway. The regional Trenitalia train Naples/Paestum is 6.50€ one way. . Metro tickets are about 1.50€ for 90m and the Circumvesuviana would be a couple of euro each way. I would think you could visit the museum in Naples and then Herculaneum on the same day using the majority of the cost of the pass and perhaps take the Circumvesuviana on to Sorrento for dinner before returning to Naples (in normal times it runs until midnight). The 3 day Campania and the 3 day Napoli (21€ - only good for Naples/Naples transport) are the only artecards that include transport.

https://www.campaniartecard.it/campania-3-days/?lang=en

Last time I purchased an Artecard it was in the Naples train station down one level. I don't know what may or may not survive covid, but I'm sure the artecard website will have a list.

Thanks Kybourbon, you once again have the information that makes travel planning much easier for me. I appreciate your help so much. That means we will then have more time to explore the AC towns we previously had not seen. Amalfi, Priano and maybe a boat trip along the coast for lunch.

In regards to Sicily, it seems like Taormino is a like it or leave it destination. Some folks felt it was too touristy. Based on my plans we would fly in to Catania around the 11 of October. I planned on a few nights there, then heading to Taormino. I had also read where it would not be as busy that time of year.

I would appreciate hearing folks thoughts on these two spots and travel time in each area. I know my wife would probably be a bit apprehensive about visiting Mt. Etna. She probably would enjoy a vineyard.
As always, thanks for helping us along
Safe travels.

If Ravello isn't on your radar, put it on there, worth going up there, among the AC towns.

I've only stayed once in Catania. It's not bad but I would only stay if it's close to some other attractions to drive to.

I've stayed a couple of times in Taormina. It's fine but difficult if you have a car. There is bus service to the garage, which is some distance and uphill from the town center. Above Taormina is Castelmola. You can hike up there but there's also a bus. Great if you enjoy sea to sky views. You can also take the bus to it and hike downhill for a nice afternoon.

Otherwise, Taormina is kind of out of the way from other Sicily attractions, unless you plan to go to Milazzo and go to the Aeolian Islands or go to Messina to ferry across to the mainland.

Much prefer staying in Siracusa -- Ortigia -- or Ragusa.

Totally agree with SCRB. Ortigia and Ragusa have that special je ne sais quoi magical vibe 'that a name might stain'.
Btw, have you checked out little Petralia Soprano?

I am done. the isle

I have nothing to add to this post made by mcsles other than, how lucky can you get with the replies to your questions. Every poster, on this thread, who has a "join date" with Fodors 2008 and older, I remember well! They are the best of the best. They give honest, unbiased, suggestions based on years of travel expertise. Hey, probably all of them helped me with one problem or another when I was active on Fodors.com.

our Sicily itinerary
 

For what it's worth, here is our personalized itinerary for September we developed with Sicily Activities. Fingers crossed this second attempt isn't canceled! I will note we decided to not devote a large amount of time to Greek ruins...we've been fortunate to see many on our travels. This however will afford us the opportunity to see them UNDERWATER on a dive to a spot where a Greek vessel carrying columns off Taormina sunk over 2000 years ago!
​​​​​​Day 1: Afternoon arrival to CTA and transfer to Taormina.

Day 2: Etna ascent until 1900/3000 mt and lunch in Etna Winery.

Day 3: Diving and Boat Tour with swimming in Taormina

Day 4: Trip to Noto, Walking Tour and Lunch in Marzamemi. Transfer to hotel in Syracuse.

Day 5: Day Trip to Modica & Ragusa with chocolate and cheese tastings

Day 6: Siracusa Olive Farm & Winery Tour with lunch

Day 7: Transfer from Syracuse to CTA in the morning

I am kane, mku4440, thank you for your posts. I agree wholeheartedly with your thoughts on the Fodor’s friends who have posted on this thread. I have said before and here again, the information I receive on this site IMO gives me a clearer picture of what I may expect when I am on my vacation. I try my best now to provide for my wife( Laura ) and my time away with the most exciting sites, hotels and meals. You are my eyes 👀 having never been before. I only use the internet and guides as a beginning. Thanks everyone.

I am curious for those who research where to eat great food without breaking the bank, where do you find this information. For instance, I was researching transportation from Positano via Ferry etc. and I came upon Ristorante Da Adolfo Di Bella Sergio. A beach lunch spot only accessible by boat with a need for reservations months in advance. I think my wife would really enjoy the experience. I would appreciate any food restaurant recommendations that you felt were special on your previous tips. Even a visit to an olive farm or winery As well.
Thanks

Have you watched Stanley Tucci's "Finding Italy" series on CNN? If not, I highly recommend. He gives great overviews of several of the regions you will visit and what cuisine is special to them.

I watched a foodie show that featured a fabulous breakfast/cafe place in Noto named Caffe Sicilia. Had the best granita that they have for breakfast. I would go to Noto just for that! I also sign up for Conde Nast Traveler and Travel and Leisure emails. They often have articles about special places to eat. I just save them to a folder. For instance there was an article about the cheapest Michelin Star restaurants in the world.

Christm907, mku4440 thanks I will give that a try. I have Google mapped the Tucci spots. I also did them for Bourdain as well as most recently Bobby flay spots. We love food well cooked but don't enjoy overpriced, small plate too fancy style restaurant.

Christy, in Noto one finds Costanzas, a gelateria whose product not only slayed the nearby and trendier, Bourdain-endorsed competitor, but for a while had Mrs Z and I wondering whether they were the best anywhere on the planet. Just outstanding quality, plus excellent service.
I am done. the Ital-foods

I spent one night in Noto just to see what it looked like at night.

Some nicely lit buildings including the Duomo, which is of course beautiful in sunlight, particularly golden hour sunlight, as well.

I agree with above poster to make your way to Ravello during your AC travels. SITA buses and taxis can both get you there.

I heard taxis are like 30€ each way to Ravello from Amalfi.