3 weeks in Italy April 14, 2015 - May 5, 2015

If you want to have that week of car travel, it makes most sense to do it where the train is least efficient.

Between Orvieto and Siena (or the hill towns to the east) all the train routes are intercity 'milk-runs' that have to transfer at Lake Trasimeno before heading toward another transfer point in Perugia. Meaning it takes longer to get from Siena to Assisi by train than is does to get from Rome to Bologna (4+ hours).

While if you picked up the car in Orvieto, you could be in Montefalco in just over an hour.

Plan your car tour from Orvieto to Siena, then pick up the train again for the rest of your trip.

A rental car is a useless expensive hassle in the following locations:
Rome, Florence, Cinque Terre, Venice, and also Siena.
A rental car is very useful everywhere else you mentioned you want to go, particularly Tuscany's hill towns and the Dolomites.
If this where my trip, considering what you want to visit and that you have 21 nights on the ground I would do (in parentheses the number of nights in each location):
- Rome (5), with a day trip to Orvieto by train, about 1 hr each way.
Train to Cinque Terre
- Cinque Terre (3)
Train to Florence, visit Pisa for one hour along the way.
- Florence (3)
Rent car in Florence and head out to a Tuscany location near Siena (around Colle Val D'Elsa or Monteriggioni)
- Tuscany location (4), with day trips by car to various towns including Siena and Assisi in Umbria. Note that Siena's historical center is closed to traffic, so if you decide to base yourself in Siena, you need to choose a hotel outside the pedestrianized area.
Drive to Dolomites, about 4 to 5 hours all freeway. Base in Ortisei.
- Ortisei (3) with driving around the mountains from there.
Drive to Venice, about 3 hours if you take the Pordoi-Cortina scenic route, and return rental car at Piazzale Roma upon arrival
- Venice (3)
Fly home
The total is exactly 21 nights. Your car rental is limited to about 8 days, and only where it's really needed. Adjust a night up or down according to your preference if you wish.

I agree that from Rome you should go to Orvieto and pick up your car for Tuscany/Umbria, then drop the car off before you go to Florence. You could stay in an agritourismo or two and day trip from there, one near Orvieto and perhaps one near Siena or Lucca.

EDIT: I just saw Robertos advice, and its good. Definitely consider his plan.

Another alternative to the itinerary above is to do Florence before the Cinque Terre and rent a car at the Cinque Terre (La Spezia) to return to Tuscany and then drive to Dolomites. In other words:
Rome > train to Florence > train Cinque Terre > Rent car in La Spezia drive to Tuscany near Siena> Tuscany > Drive to Dolomites > Drive to Venice and return car.

Thank you all for the information. Roberto, I think your second suggestion looks very workable & we will probably use it as a template for our trip. All of your help is greatly appreciated.

Well, don't I feel silly. It appears that we might be a little early for the Dolomites. Looks like most (if not all) of the lifts won't be in operation yet. Does anyone have any ideas what area we could visit to replace the Dolomites?

Thanks again for all your help!

Dolomites are beautiful in April. Just be careful for winter conditions, sometimes winter lingers a bit longer upthere and it could snow. April is low season (in between skiing season and summer season) so you will save some money too.
Otherwise in that area, Lake Garda and Verona are nice alternatives.

Hi drpah 111,
1. I would download app TRENIT where you will find details on time spent by train from a city to another. You will also find the cities you will pass through and the price of the ticket which you can order online (should you not have an address aly, just put the address of one of your hotel, that will do).
In that way you will be able to decide how you want to organize your vacation.
For example, you might want to visit the toscan Isles and the Isle of Elba and take the traghetto at piombino, spend two or three days on Elba island, then on your way back continue to the mainland, go from Cecina to Volterra for instance. You could also rent a car, do all the hill towns, etc . Do not miss Volterra.
I would go to Cinque Terre by train( Monterosso) as the best way to see these villages are either by walking or better - if you can sail- rent a sailing boat and discover these villages by the sea.

I would have left Venice and the Dolomite for another vacation, so as to concentrate on two regions, Umbria and Tuscany. There is already so much to see.
Keep calm and enjoy your time.
I would instead add Perugia and Gubbio.

Roberto has given you excellent advice. Ortisei is a delightful little town nestled in the mountains. While it is early for the Dolomites, it is still beautiful. With a car you can get to several lovely valleys and towns easily. For hiking you may need to stick to lower elevations, and there are several you can take without taking a lift. In the Val Gardena/Ortisei, on arrival consult with the TI and the Val Gardena Active/Guides Catores for what is open and possible. I would go there any time of the year in a heartbeat.

Arrive Rome for 4 day visit. Train to Cinque Terre for 3 day visit. Train to Florence for 2 day visit. Rent car last day in Florence. Drive to Siena. Use car to travel Tuscany/Umbria. Maybe a wine tour day to Montalcino and Montpulciano. Or down to San Gimignano and Cortona. Volterra on a week day. Keep car and spend a night in Verona on your way to Castelrotto/Val Gardena. From Castelrotto, you can drive the Great Dolomite Road through Cortina d Ampezzo to Mestre/Venice. Drove this route the opposite way, from Mestre to Castelrotto, in late May 2 years ago. What a fantastic drive. Do expect snow in the mountains in April but it should not affect the strada too much . Drop car off in Mestre, spend 3 nights in Venice before your flight home.

I should have said "drop your car off at Marco Polo"...Mestre would be the end of the line for train travel.

We did the opposite itinerary and arrived in Venice and flew out of Rome (but did not do the Dolomites). We used the train to get from Venice to CT to Florence and once we were done in Florence, we got the rental car to drive into Tuscany. Our base was an agriturismo outside of Pienza that we got from the RS book (Fonte Bertusi). We thought it was a great central location for most of Tuscany and Cortona wound up being the farthest we drove -- about two hours one way, but we were also able to get to Siena, Montalcino and Montepulciano quite easily and stopped at towns on our way down from Florence and on our way to Rome (we really enjoyed Civita di Bagnoreggio).

We dropped our car as we arrived in Rome near the Borghese. There are always a lot of people that say to pick up/drop outside of town, but when we looked at the pricing, it was far cheaper to do it in the cities (esp. when factoring in the costs of the train to get to/from the hill town) and while the traffic was a little busier than what we were used to, my husband said it was manageable for him to save the costs.

The one thing I'd caution is that the hill towns are true to their name and the roads are quite steep and hilly, so you need to be fairly adept at driving the manual stick -- for us, the burden of driving was mostly on my husband. You can try to get an automatic, but I've heard that isn't always a guarantee.

I posted this elsewhere but maybe it will help.

Our 2nd trip in 2012, we stayed at Agriturismo Cioccoleta Orvieto just 3 miles or so out of Orvieto. In fact, while there, you're looking across the rolling hills at Orvieto in all its glory. When you arrive at Orvieto by train, cross the front parking area, then a street, and Hertz is just across the way. Rent a car to get to the agriturismo, and take the opportunity to visit other areas nearby, such as Civita di Bagnoregio like we did. When visiting Orvieto, there's a nice parking garage with escalator or elevator on the north side of town. Or park near the stazione and take the funicular. We parked north of town and just took our time.

Spring 2014 we based in Firenze for a week and just took rail and bus to various places for day trips, like Lucca, Siena, for example. We also toured with Rick Steves buddy Roberto Becchi into Montalcino and Torrenieri, etc, all day. And of course visited sites we hadn't visited in Firenze on previous trips.

Then we stayed a week in Cortona. We ventured out into the Val D'orcia, Montisi, sites where Gladiator and English Patient were filmed, Pienza with our friend Luca Garrapa who runs Hills and Roads car or van tours out of Siena.

I didn't do this but was ready to- take a train to Chiusi just SE of Montepulciano. Cross and go up the street a little from the stazione to Hertz and you're now free to visit Pienza, Montepulciano, Montalcino, all over southern Tuscany, stay at any of the many agriturismos, and then return the car to Chiusi and hop the train to wherever. My next trip will include this so we can stay at Sant'Anna in Camprena where English Patient was filmed (90 euro night, and 20-25 euro per person for dinner with wine), and home base there a few days, and then stay with our friends in Cortona.

I try to avoid having to drive in Italy but in rural areas of Umbria and Tuscany it's no problem. Just get the super cover insurance supplement to get the deductible down to ZERO. Otherwise, any damage will still incur a significant chunk of change.

You have all been extremely helpful and so forthcoming with all your knowledge. After much research and consideration, here is the itinerary we have decided on:

Rome (4) We may decide to use the extra day for a day trip to Pompeii
Florence (4) With a day trip to Sienna
Cinque Terre (2)
Pick up car in La Spezia or Pisa
Then drive to Orvieto - home base (4)
Verona (2)
Ortesei (2) Roberto & Lauren were very persuasive in their arguments for the Dolomites in general & Ortesei in particular
Venice (3)

How does that sound? I know that Orvieto is a little south for a home base, but I just have a thing for the town.

You're really backtracking going back to Orvieto. This is a better path.

Rome 4 nites

Train Rome to Orvieto. Rent a car here for 2-3 days. 4 nites.

Train from Orvieto-La Spezia 2 nites.

Train La Spezia-Forenze SMN. 4 nites.

Rent car 4 days

Drive Firenze-Verona 2 nites.

Drive Ortisei 2 nites.

Drive Venezia drop car. 3 nites

Looks like a nice trip coming together.

I think going to Orvieto after Rome just makes sense and you'll appreciate the time you save not having to backtrack. I love Orvieto too, and the reality is that you could run out of time and decide you can't backtrack to visit it.

Time is precious when traveling. Make the most of it I say.