Best way to travel Italy on our own

A couple years ago we flew into Milan, rented a car and stayed at the Villa Belvedere on the East side of Lake Como right on the water; free parking & a very short walk to the ferry terminal that's will take you to a number of small towns including Bellagio. Years before that we also flew into Milan and drove to Bellagio (it's a very long drive up to Bellagio and the roads were not the greatest; also Bellagio is very hilly). Easier to stay on the side of Como and tour the lake on the Ferry; on this one we then drove to Venice and dropped the car off and took a cruise.

This last time we then drove to Cinque Terre and stayed in Levanto with free parking and took the train to the 5 villages. Spend the next two weeks in a Villa in Tuscany then drove South to Positano at the Albergo California with free parking for 3 nights then to Rome for 4 nights. We dropped the car off in the outskirts of Rome & took a taxi to our B&B. We find driving the easiest and most economical but you do need a GPS. We stated at the Navona Gallery Suites in Rome.
There isn't a drop off fee within Italy but you do need an International Drivers License which is cheap at your local AAA or CAA.
Hope this helps,
Jean

Thanks for the quick response! In a little while we'll be talking to friends who live elsewhere from us but who have been to Cinque Terre several times; I'm really concerned that I won't get to do much because I can't walk a lot (I can do about a mile or so a day, no hills).

Several friends have really warned us off of driving, although that was my original intent.

I’d concentrate on the Naples region (Amalfi coast, Pompeii, Sorrento, Capri, Procida, Naples, etc.).
Early April the weather may not be settled near the Alps. Also the two locations are almost at the opposite ends of the peninsula.

Thanks for the reply. We know the 2 locations are far apart, however I believe if we fly into Milan, go to Como, then we can either fly from Como to Positano or Como to Rome and take a 2-hr train ride to Positano. We've been in Naples and the surrounding areas. If you're familiar with Italy does what I've posted make any sense to you?

Appreciate any input.

Depends on how much time you have; we did our driving tour of Italy with 2 weeks in a villa in 3 1/2 weeks. Driving is Europe is easy especially if you've driven in any big city. We live in the Toronto area which has the worst traffic anywhere so Europe isn't hard; we've driven France, Belgium, Italy, Germany, Spain, Portugal, Great Britain & Ireland and always stayed 2-3 nights; no one nighters... don't drive in the big cities like Rome, we parked at the train station in Florence, it's a short walk to the Duomo & museums ; just stick to the rules & have a GPS.

Cheers,
Jean

Flying from Como to Positano is not an option. Neither has an airport.
The closest would be flying from one of the Milan airports to Naples. However once one takes into consideration the transfer times from Lake Como to the nearest airport and the airport security procedures the train may be actually faster and certainly more comfortable.
You can take a train from Varenna on Lake Como and get to Naples Central in less than 6 hours (one change necessary at Milano Centrale). You’d need about the same time for flying from Milan to Naples, once everything is said and done.
Add another hour from Naples and you can be in Sorrento. Positano is an additional 45 min down the road. Actually I’d suggest a private car transfer from Naples to Positano. More expensive, but way more comfortable than the Circumvesuviana train and the SITA bus.
But no matter what, it is a long day traveling.

while technically not on the amalfi coast...sorrento is a great place to hit all the major sites and has a great night life...food...drinks...great place to chill

Check local tour operators like Viator (51 Cinque Terre tours) for easy walking tours or consider a boat trip along the Cinque Terre coast.

I remember the CT as being very hilly. Positano is one of the most hilly AC towns. The center of Sorrento is mostly level, with an uphill (not steep) to the train/bus, and a long steep way down to the sea - there are elevators and buses and expensive taxis). Salerno is very walkable; it's level and you can take buses and ferries to everywhere along the AC. It's easy to get to by fast train from Rome or Naples. From Salerno you can take the train or bus to Paestum - level walking - for the Greek temples. In April, unless you are there around Easter week, it shouldn't be too crowded on the AC, so consider renting a car if you are used to mountain driving. Here's a description of my experience. The AC towns are not particularly interesting, but the views all along the coast are gorgeous.

Thank you to everyone for your responses. All your input is very helpful.

Thank you again to everyone who has replied, very helpful. Thanks to Jean H. we've already booked the Villa Belvedere. I continue to read multiple responses about driving vs. taking trains to get around. Our tentative plan is to start in Como for 4 nights (probably from the Milan airport), then start our way to end-up in Venice with stops in Veronna and Padua. Seems like for every person who says driving isn't bad, there's an equal number who say why drive, take a train. The only time we took a train in Italy was from Abruzzo to Rome, only negative was getting the luggage on-board, thus while we can't take cars into cities, seems like it might be easier for luggage purposes.

So, here goes:
1. Train or car? I'm wondering if we take a train will we miss the opportunity to see some quaint villages, etc. along the route.

1. If we use trains, buy the tickets on-line while still in the States?

Thanks in advance to anyone who responds.