which would you choose. 5 nights in Tuscany or The Amalfi Coast

If you really want Tuscany, go to Tuscany. It really can be done by train or bus. You could just rent a car for 2-3 days while there to explore wineries and hilltowns, but still use public transport for the most part.

You don't need a car in Tuscany. It's true that you can reach a lot of the smaller towns more easily by car than by bus or train, but you're only going to be there five days - how many towns were you hoping to hit?

You could split your time between two locations (say 3 nts Siena and 2 nts perhaps in Cortona) and have a day trip from Siena by bus in your back pocket as an option. That would give you time to actually experience Siena and the other town you choose.

This website is a good reference to figure out where to go:
http://www.raileurope.com/europe-travel-guide/italy/map.html

This is another one: http://www.rome2rio.com/

Tuscany and the Amalfi Coast are both fine destinations, but I'd choose the one that interests you the most. I agree with the two posts above - a car isn't absolutely necessary in Tuscany. You can take the train and/or bus to Siena and use that as your home base. From Siena you can visit other nearby hill towns by bus, such as San Gimignano or Montalcino, or take a mini-van tour from Siena for the day, where you have a local guide driving you around to one or more hilltowns. This is especially nice if you would like to do some wine tasting, as then you don't have to worry about driving. "Roberto's Tuscany Tours" based in Siena, has several different itineraries - www.toursbyroberto.com. You can always rent a car for the day in Siena to do some exploring on your own.

Jay, I don't see that you have indicated what month you are traveling. In poor weather, I think the Amalfi Coast would be less enjoyable, many boats would not be running, etc. Also, the AC is far more distant from the Dolomites and from Milano, so you would spend probably an extra half day or more in transit, each way going to the AC and then back north, over the transit time involving Tuscany. There's a lot more diversity to explore in Tuscany I think. Of course the heart of Tuscany is Florence, and neither you nor anyone else has mentioned that so far. I have visited many cities and towns of Tuscany without a car, by public bus, by train and by day-long tour. Depends a lot on your particular interests and the month, but I would encourage visiting Tuscany this time around.

Thanks Larry....sounds like great advise.

You're talking about my 2 favorite places in Italy! I never drove in Italy my first 4 trips but took a rental car around Tuscany last year hitting many of the small towns and it was easy. Still don't think I'd take on driving in Amalfi Coast, but if I went there I would stay in Sorrento. It is a transportation hub with easy access to trains , buses and ferry to Capri. I agree that November to March I would definitely choose Tuscany.

If you already have a car in the Dolomites keep it and drive to Tuscany.

The scaremongering you read from people traveling to Italy about driving there is largely mythology from people who never drove there because didn't have the guts to try and now don't want other people to try either.

If you plan to drive in the Dolomites, Tuscany is actually easier. Driving in Italy is not any different than driving near your home. Just drive the Ortega highway from San Juan Capistrano to Temecula and that is the Tuscany driving course for you.

Restricted traffic zones are only inside historical centers (I.e. Inside the city walls). Just park in one of the many lots outside of the city walls and there is no danger of getting a fine.

With five people, would it be easier to rent and drive a larger car, rent two cars in case you want to split up occasionally, or take trains and buses so you can all be passengers?

Jay, you already have received some excellent replies here. I don't mean to sound pedantic, but your OP is extremely vague about your potential plans. Quick readers may even think that you plan to stay in the town of Amalfi, but I don't think you meant to write that. Personally, I'd choose Tuscany from the menu you offered, even though we enjoyed our five nights in Sorrento last May.

It sounds like you aren't wedded to having the freedom of a car. That's good, because a car can be very troublesome on the Amalfi Coast (AC) due to two-lane roads, traffic, and non-existent parking. Will you have a station wagon, or some sort of van? The bigger, the harder the parking, if you can find it. But your OP mentions training to the AC. The long-distance rail system has a stop at Salerno, and the local commuter line (in-building change in Naples) ends at Sorrento. Are you thinking of staying in either of those places? If not, your group is too big for an expensive but pleasant Executive sedan transfer, so you'll be making the backpacker transfer on a crowded bus. (You still haven't said In or Out of season yet, have you?)

To put that more clearly, with the dubious exception of Salerno, there a NO trains to the Amalfi Coast. I hope you have read the hilarious thread about AC in a day by car: https://community.ricksteves.com/travel-forum/italy/rome-day-trip-to-amalfi-positano-pompeii-by-car

Once you're in the hotel, I don't see enough to do in, say, Positano, for five people. Sorrento is much better located for five people who don't all want to do the same thing on any given day, but want to meet for dinner in the hotel town. But lots of posters here find Sorrento to be lacking romance in comparison with Positano or Amalfi. One reason for that is that there are so many hotel rooms in Sorrento that some of them are a long way from the water, and some don't have any view. Naturally, the better the view, the more expensive. There are virtually no beaches in Sorrento, but I didn't care for the stone beach with pay-chairs in Positano. Some people find it as exciting as watching Lives of the Rich and Famous, however.

Consider a small villa in Tuscany and do day trips by car. Parking at a villa is usually not a problem. Our family has done it many times. Parking in Siena is easy peazy. Hop a train to big cities like Florence for day trips. We have spent a week on the Amalfi Coast (Positano). After two days I drove the rental car back to Naples and dumped it. We used the bus and boat systems, but even so it was hard to get around. Buses are packed during tourist season. We had to wait for a second bus a couple of times.

I am biased, I like Tuscany, and even Umbria.

Have a great trip.

Roberto - I must ask: are you a billionaire who constantly circumnavigates the globe? I am truly impressed with your clear and concise "travel knowledge" reporting!

Jim_Bird
If I were a billionaire I wouldn't live in Fremont, CA. At the very minimum I would move across the bay to Palo Alto or Los Altos Hills, where lots of Silicon Valley billionaires live. I'm on the working class side of Silicon Valley, where the Indian software programmers live.
My knowledge of Italy comes from a few decades living there. And when you live in Europe you don't need to be a billionaire to see things. All those great places are a short distance away.

Tuscany is the only answer in my book. We were in Tuscany in July and had a rental car the entire time except Florence. Each day was like driving through an oil painting. The drives around Pienza and the Val d Orcia are so beautiful -- it's hard to describe. I recommend staying in hotels that are very close to or in the small towns. There are many that have parking nearby or on site and you can walk to dinner at night and not have to worry about driving back to a place out in the country. There are no street lights on those rural roads.
We stayed 3-4 nights in several places, using them as a base and then drove short distances to the hill towns or wine areas. Don't fret about the ztls--they are clearly marked and every town has parking outside of the walls. You will need to brush up on using a stick shift as most cars are manual. English speaking GPS makes driving easy, but it did not seem to recognize the ztls so don't follow it blindly into town. Good luck.

Take it from a 60 year old grandmother.....driving the Amalfi coast is a blast! Parking, however, can be a big challenge! Choosing between Amalfi and Tuscany is like trying to choose between a ruby and an emerald....you can't go wrong. For me it would come down to the time of year....I am a heat-a-phobe, so, summer along the Amalfi would be out for me. September in Tuscany is wonderful - grape harvest time.

You cannot go wrong!

Car is not a problem in either place. (For me, trains are the transportation issue/discomfort level rather than cars having done both). Both places are wonderful so go with the one you really want to see. Don't let the car train issue decide it.

Roberto,
Maybe so, but anyone who can comment on vintage steam locomotives servicing the Garfagnana and has driven the Ortega Highway is a true Renaissance Man! I've driven the O highway twice and I've lived in the OC for 40 years.