About two months in Italy

I haven't been to any of those places, but I was just looking at seat61.com, as I often do, and it offers alternative ways of getting from Rome and Naples to/from Sicily via train and ferry and a train that goes on the ferry. Have a lovely time.

Another option would be to go to Stresa on Lake Maggiore instead of Lake Como. It’s flat, and Isola Bella and Isola Pescatori are wonderful to visit by the little ferry. Transportation from Stresa directly to Malpensa is available by Alibus.

We like Hotel Ala in Venice because you don’t need to cross any bridges with your luggage, and it is near San Marco.

A website I like to use is www.rome2rio.com to look at transportation options for any two locations, including from the train station to your hotel. The left column will show which company to go to their site and see actual transportation time & how often it’s available.

What time of year will you be traveling?

Do not trust the transportation times, frequencies, or fares provided by Rome2Rio; they are incredibly unreliable. You need to keep clicking through the website to find a link to the train or bus company providing the transportation. That's where you can (one hopes) get accurate information.

If you can manage close to 3 weeks in Sicily, I highly recommend it. It is a fascinating place with great sights stretching all the way across the island. You'll need quite a few bases in order to see the key spots. Palermo needs considerably more time than Messina (unless you are meeting up with family in Messina, of course). Do not under any circumstances try to drive in Palermo. A car will be helpful elsewhere in the western part of the island, in the interior (Piazza Armerina, Enna, Caltagirone, etc.), and for seeing the small Baroque towns outside Siracusa (Ragusa, Noto, Modica, Scicli). One can do a decent job of seeing Sicily via train and bus, but a car will often be more efficient, so mixed modes of transportation would work well.

Do not be tempted to take the night train from Rome to Sicily. I cannot call it a nightmare because I never slept a wink, but it was a miserable experience. I think flying is a fine idea. You will have plenty of other opportunities to take trains in Italy.

In addition to the areas you've mentioned (which are wonderful), I enjoyed some time based in Padua in 2015. Padua has several very good sights and is an excellent base for day-trips by train to Vicenza, Ravenna and Ferrara. I have not been to Ferrara, but the other three are basically flat. Padua's quite close to Venice, so if you don't mind paying Venice hotel prices to take an out-of-town trip, you could see Padua very easily while you're staying in Venice. Vicenza wouldn't be a crazy idea.

When people start planning long trips, the trips sometimes get even longer as they dig into guide books. If there is any possibility at all that you will be in Europe for 90 days or longer, please come back here and tell us that. We need to be sure you understand the Schengen Zone time limits.

As acraven says, the best way to/from Sicily is to fly. You need a minimum of 2 weeks, more is better. While there are several good choices for a base on the eastern and western ends of the island, there are some great towns and sights in the middle, so 3-5 nights spread out over 3 places is recommended and you will want a car. It probably doesn't make much difference which end you start at. Fly into one and out of the other.

I don't know which gets more crowded faster, Sicily or the Amalfi Coast. You may do better to be on the AC in early May than late in the month. I don't think it would make much difference. If you start on the AC, you could fly from Sicily to Tuscany. While Sorrento is a good base for day trips (Capri, Pompeii and other archaeological sights) I wouldn't plan to stay there if your main interest is the Amalfi Coast. Better to stay either in one of the AC towns or Salerno. Salerno has an interesting historic center, a large sandy beach, lots of good bars and restaurants and fast train connections to the north. If you want to explore Naples, then you should spend several nights there.

Instead of Tuscany, consider Umbria, or maybe both.

For Sicily I would rent a car, except for the time while you are in Palermo (maybe at the start of your Sicilian stay). The traffic in Palermo is such that it is best to rent a car after you visited the city on your way out. After Palermo I would stay in Scopello and use it as a base for western Sicily. Then visit the island in a counterclockwise trip. You can end your trip in Palermo from where you can fly out. If the flight is later in the day, I prefer to stay in Cefalu.

The rest of your plan sounds good. If you fly out of Milan Malpensa, consider a few nights in Stresa before your flight home. Only 45 min from the airport by car.

I would recommend bases in these areas:

• Palermo
• W of Palermo (I don't do beaches, so I chose Trapani and day-tripped to Erice)
• The interior
• Siracusa (and hit the Baroque towns)
• Catania/Taormina (prettier but much more touristy)/etc.
• Messina
• Plus probably an extra place or two if you want to see some of the Greek ruins at Agrigento, Segesta and/or Selinunte. I skipped those and don't know how well they'd fit in with my other suggestions.

But again, time of year is critical. Sicily will almost certainly be miserably hot in mid summer. In late June/early July it was unpleasant. Having an air-conditioned car for transportation would help to some degree, but still, you'd be mostly outdoors or in non-air-conditioned buildings during the daytime.

Landing in Naples, you have a few choices of transportation.

Private driver to the Amalfi Coast.

http://www.sorrentosilverstar.com/sorrento-silver-star.html

The town of Amalfi is the best bet for ease of bus and ferry connections.

Curreri Viaggi bus to Sorrento. Timetables here.

http://curreriviaggi.it/autolinee/images/AUTOLINEE_CURRERI.pdf

Or taxi to lodging in Naples. Fixed rate card.

https://www.napoliunplugged.com/wp-content/uploads/2018/03/Tariffe_taxi_2017.pdf

I would try to spend a full week in this area, there's a lot to see in Campania.

There are 2 cards that may save some $$ on sites.

3-day. 2 free sites. Up to 50% off on however many you can fit in. It includes transportation on bus, metro, funiculars and some regional trains.
Cost is €32

7-day. 5 free sites. Same 50%. No transportation.
Cost is €34.

We have driven from Naples to Tuscany many times. I'm also older than you by 4-5 years, so yes, you can do it.

Several options for a rental car. Sorrento and Capodicino Airport. Use either autoeurope or Europecar have had no problems with either.

The other option is to train to Chiusi and pick up a car there for the Tuscany portion.

We love this lodging. It's not in town (10min.) but up on a hill with its own little castle. Great owners.

http://www.borgorapale.it

Hope this will be of some help, your trip looks fantastic !

Looks like a lot of good advice! Thank you ALL!
Lake Maggiore sounds interesting instead of Lake Como and Borgo Rapale looks like a good fit for what we are looking for around Tuscany. Would appreciate any other suggestions for places to stay in:
Venice
Naples
Amalfi Coast towns
Lake Maggiore
Florence - maybe an apartment across the Arno near Bobili Gardens
Sicily
We will be carrying luggage - one large suitcase and two carryons.
Thanks in advance!

Roz,

We didn't end up staying here two years ago because there ended up being three of us. I still had it in my notes and they're still showing it on booking. It's in a very central area, and looks adorable.

http://www.booking.com/Share-Ae3DJu

Roz — You should reconsider your luggage plans. You will get really tired of lugging that big suitcase around. Much better to read all the “packing light” suggestions on this website and limit yourselves to a carry-on size suitcase and a personal item for each of you. You’ll need to find laundromats or do sink washing, but it’s a good trade off for the freedom from that big suitcase. You’ll get tired of wearing the same clothes over and over but no-one else will notice.

I totally get the luggage suggestion. Would LOVE to travel with less, however this trip will be at the end of a long transatlantic cruise. By the time we end this trip we will have been traveling more than three months and a variety of weather conditions.

Considering the inconvenience of schlepping too much luggage around Sicily and Italy for a TWO MONTH PERIOD, including paying extra on planes and having to personally handle everything as you train around or drive around the country, I would pack up most of my luggage and have it shipped home via Mailboxes Etc. There are a number of storefronts around Rome.

Good suggestion on our luggage situation. I do have some time to think it through more carefully. Would LOVE to travel light! :)

Maybe you can figure out a way to build a wardrobe around the casual things you'll want in Italy and add a few very lightweight dressier over-blouses and scarves to fit in with the cruise crowd. The only thing more miserable than a large, heavy suitcase is a pair of shoes that hurt your feet.

In addition to the physical misery and the real possibility of a strained back, a large suitcase can constrain your travel choices--it's reasonable to be nervous about 8-minute transfer times in train stations that may not have working elevators, and you may decide that lodgings without elevators--however charming and well-located--just won't work for you.

Roz, I forgot to add the link for the cards in Naples.

http://www.campaniartecard.it/artecard/en/content/luoghi

Click on the type of site, then by name, scroll down,click on banner, gives you info, plus prices and opening timesand if you again scroll down
You get a few pics and another map.