Our tentative itinerary is this:
2 nts Venice
2 nts Florence
4 nts Cavriglia
3 nts Rome
4 nts Sorrento
2 nts Naples

I've been looking at train transportation options. I priced it out, and it seems like it's cheaper for individual tickets than the InterRail Pass. Does that make sense?? I thought the pass was supposed to be a discount?

Our other question is this...any advice would be great!

We have two options - below. No matter what we'll likely fly into Venice and take a train from Venice to Florence, then once we're in Rome take a train from there to Sorrento. It's the middle part we're not sure about! Our options are:

1. Pick up a car on our way out of Florence and drive to Cavriglia. I'll be taking a workshop at a villa outside of Cavriglia for four days (http://www.chianti-farm.com/), so it might be nice for my husband to be able to easily get around and explore during those four days. The villa seems to be a bit outside the city, so it might not be super easy to get into the city for transportation - plus I don't know if a city that size would even have taxis or anything. We'd drive to Assisi for a half day visit or so, then return the car in Perugia (no rental return in Assisi!!) and take a train from Perugia to Rome. Depending on time, we might skip Assisi. This pricing option seems to be $530 ($281 car, $250 train once converted from euros to dollars). Another plus is that we have a bit of flexibility to explore on the way to Perugia. It might also be a nice change of pace from the trains.

2. Do all trains - so Florence to Assisi, Assisi to Rome. The possible downside here is that we might end up spending just as much on trains/taxis as we did on the car. This pricing option seems to be $418. The upside, of course, would be that we don't have to worry about getting/returning the car or trying to figure out how to drive in Italy. There is a shuttle from our villa to the Florence airport, so we wouldn't need to worry about transportation to and from Florence and Cavriglia (I believe).

Thanks so much!!!

You are correct. Rail passes hardly ever make economical sense in Italy since the prices are relatively low.

With you special time in Cavriglia, I'd suggest option 1 with the car. Other popular options (instead of Perugia) for returning the car that might have better train connections to Rome are Orvieto, Chiusi, and Foligno. If you choose to skip Assisi, you might head directly to Orvieto for a visit there, turn in your car, and hop the train to Rome.

If you are from the US, I don't believe you can't get an Interrail pass anyway. I think the Interrail pass is for Europeans. There are other rail passes for US residents, but they are almost never cost effective for Italy.

I think you need to tweak your itinerary. Are you flying home from Naples?

Did you price cars on Autoeurope? Many times a 3 day rental and a 7 day rental are close to the same price. I would look into renting in Florence and returning at Chiusi or Orvieto.

Hi lg,

Yes, train tickets are often cheaper than a railpass in Italy.

Go for the car.

Enjoy your visit.

I love the trains in Italy. As much as for any other reason, it's a much more relaxing way to travel, especially as those pesky Europeans insist on driving on the 'wrong' side of the road compared to us Australians! It becomes so stressful that it's not worth it. Trains on the other hand provide an enforced rest break, and a chance to enjoy the views out the window.

Even if ultimately the train travel does end up being slightly more expensive, it would still be my choice as it's so much less stressful.

Hope you have a great holiday, it sounds fab!