You do not have time for 5 destinations---4 will be a stretch.
Sicily is the obvious outlier---save it for when you have at least a week.

How many nites will you sleep in Italy---11 or 12?
With 11. I would consider only 3 destinations.

When you stay somewhere 2 nights that only gives you 1 full day in a location. Everytime you move you will lose 1/2 a day in transit, checking out, getting to the train station, waiting for the train, taking the train, then doing it all again on the other side.

You will barely get to these places before you are leaving again! With 11-12 days I agree that you should stick to 3 locations.

I'm going to make a gross generalization here and say the more experienced a traveler is the longer they stay in a given location. Yes, I know there are you movement junkies out there but I think it's true more often than not.

I believe, whether we think about it or not, the reason is that we come to the conclusion that we need not see every place in a given country to have a quality experience and in many cases the longer we stay in a location the better that experience is. The point is not necessarily doing things, it's just being there. And the slower we go the more we see.

It may be a thing that one must learn, cannot be taught. But in this case I'll agree that 3 places would be the most you could do and not feel terribly rushed. And don't waste time and effort with a car. Take the trains.

It looks like you have 11 days on the ground. Is that correct? Completely agree with the above posters recommendations. I would eliminate Amalfi Coast & Sicily. My suggestions:
Arrive in Venice May 2nd. stay 3 nights
Travel to Tuscany (drive ) 5 nights I think a car for this portion would be nice since you could pick one location to stay in and do day trips and a car makes that much easier to get to some less touristed towns.
Travel to Rome (train) 3nights

If you prefer big cities you could allocate more time to Rome and less to Tuscany and then t might not be worth it to rent a car.

I completely agree with the above comments but it's your trip and if you feel the need to move around every couple of days then that's what you decide.

When you travel you can choose to either travel to many locations and spend part of your vacation time getting from place to place OR visit fewer locations and see more of the sights in those places.

Whether you rent a car or take the train to Tuscany depends on where in Tusany you're staying. If in a city (Florence, Pisa, Lucca, Siena, for example) it's more practical to use public transportation (bus/train). If you want to stay in the countryside then renting a car is usually better.

Travel to Rome - again this depends on where you stay in Tuscany and if you have already rented a car.

Driving on the Amalfi Coast is difficult. There's lots of traffic and cars must give way to the buses. You'll be driving on narrow, winding roads with only Belgium Blocks on the edge. The driver will need to keep his/her eyes on the road and will not have much time to look at scenery.

Sicily - it would be a shame to only go to Sicily for 1 day. An expensive excursion for little time.

If you do keep this agenda then fly into Venice and home from whatever city you're visiting on Sicily.

My first trip to Italy looked like this:

Flew into Rome spent two nights

Drove to Sorrento spent one night

Hydrofoiled to Capri spent one night

Hydrofoiled to Naples and took an overnight train to Venice..

Spent one night in Venice....

All totally doable and enjoyed every second of it.

Granted, I only had a week to spend there, and I wish it could have been longer, however, it gave me the opportunity to know where I wanted to go back to. If you train it overnight from Venice to Naples, that takes care of "wasting any time traveling. The overnight train was wonderful (be sure to reserve a first class cabin as it is private for you and your husband.) I would however eliminate the Sicily portion, as it is alot to do for a short time. I would definitely do the Isle of Capri as that was a fabulous portion of my trip.

Thank you all for your suggestions so far. Yes I know I was trying to fit in as much as I could without being too rushed and I was cutting it close. Its rare we can take a vacation at all, let alone one for 2 weeks.

It seems for 11-12 days in Italy, the best option is stick with 3 locations. From what I heard, Rome and Venice are a "must" so would Tuscany be the better option for a first time visitor rather than Amalfi coast? As far as scenery and things to do/see? How does everyone rate those 4 areas?

My husband's family was originally from Sicily, and I hate to cut it out of the trip, but it seems so far from everything else for a short trip

So if we do Venice, Tuscany and Rome in that order would it be best to drive from Venice to Tuscany , then train to Rome?

I have started researching hotels/castle type inns, but can anyone suggest a specific town in each area that is the best place to stay for a first time visitor? As I stated, this is our only vacation (for a few years) so we are okay with spending more for a nicer hotel experience.

Thanks again for your help!

If Sicily is truly important for your trip, then you can fit it in. Just delete Tuscany and the Amalfi Coast.

Fly into Venice - 3 nights.

Early morning train to Rome - 4 nights.

Fly from Rome to Palermo or Catania - rent a car - 4-5 nights.



Fly home from Palermo or Catania.

Yes, do those 3 in that order.
Then, start to plan your next 2 trips to Italy since you will return. Sicily needs 10 days or more. The AC can be done in 5.
The lakes are still my favorite destination---tons of options.

I would agree with the above posters. On our 10 nights in Italy, we spent 3 in Venice, 4 in Tuscany and 3 in Rome. I wouldn't have wanted to spend less in any of those places, and more nights in Rome would have been welcome. We took the train from Venice to Chiusi (. This meant we let the "the train take the pain" for those 4 hours. Then we picked up our car from Hertz near the Chiusi train station. We used the car to tool around Tuscany, which was a real pleasure. Then we dropped it back at the same station, and took the train to Rome.

This arrangement, train then car, was suggested by many on the Fodor boards, and worked well.

I can recommend the Residenza Il Poggiolo in the village of San Quirico d'Orcia as a Tuscany base, and the Navona Garden Suites in Rome. Both were superb.

I know what you mean about where your husband's family is from. Our first trip to Italy we did the big 3 - Rome, Florence, Venice. It was fabulous! When I was planning that trip, I never thought that we would be back again in just 15 months, and with the big 3 out of the way, we made it a priority to visit where my hubby's family was from in the Piemonte region. This is just to mention that you will likely end up back again.

When we stayed in Tuscany during our 2nd trip we stayed in Castellina in Chianti. We stayed at Fattoria Tregole (http://www.fattoria-tregole.com/), a wonderful old villa with an active winery. We thought it was an excellent location and visited many small towns in Tuscany from there. We did have a car, which as others have mentioned is really necessary for getting the most out of Tuscany. I would agree with the poster who recommended taking the train close to your Tuscany location and renting a car there.

Here is a link to my trip report which also has pictures of where we stayed in tuscany:
http://www.fromhometoroam.com/2012/06/tuscany/

Thank you again for the helpful responses about order and transportation.

sformby and jgg, thanks for the details I will look into your suggestions. Jgg- your blog is great!

I'm sure I will have more questions as we plan...