First time planning a trip to Italy

You already have far too much here for a three-week visit, but it's a great start.

i would not recommend driving from Rome. Rather, take the train to your first region after Rome. And rent the car at the train station or, after your stay in the destination city. Cars are most useful in the rural areas; they are a huge hindrance IINSIDE cities and towns.

For example, from Rome, take the train to Florence. Send about 5 days there and only then rent the car and drive to the Valle d'Orcia area of Tuscany....use the car to dawdle around the various villages and towns and wineries. Then return the car to Florence, take the train to (maybe) Turin, spend a couple of days there and then rent another car to cruise around Piemonte.

End the trip in Milan and fly home from there.

But you really need to delve into a good guidebook and return here to ask questions after sorting out a basic plan..

I'd leave out the Dolomites for May..it's not a good time to be there.

If wine is a focus, and maybe food as well, maybe narrow down your trip to Rome, Piemonte, and Tuscany. Even a brief visit will fill up three weeks, easily. And May is a good time of year for both of those regions.

I second the previous reply.

Consider taking the train down to Naples and base out of Sorrento for 3-5 days to see Pompeii, the Amalfi Coast and Capri.

I would break three weeks down as follows:

Train Based:
Rome - 5 days
Naples/Amalfi - 4-5 days
Florence - 2- 3 days

Car based - renting from Florence
Tuscany/Umbria - 5 days

Return car and train to Lucca and or Cinque Terre - 3 days

Train to Milan for return flight

...a day trip to see the ruins in Pompei.

It can be done as a day trip, but, it will be a very, very, long and tiring day with an early start and late return. You might want to consider going to Ostia Antica instead. It's very close to Rome, can be accessed using public transit, and by leaving around 8 a.m. you should be able to see it all and still be back in Rome by mid afternoon.

With regard to the rest of the trip after Rome, I'm tired just reading about it. Italy is definitely a case of "less is more". Slow down and savior it, not gulp it.

Remember, you will lose at least 1/2 to 3/4 of a day every time you change locations.

As to specific suggestions, Venice is without a doubt one of the most unique places we've ever been. And Florence is another city that has to be experienced to be believed.

Perhaps a week in each is something to consider. Don't mean to be Debbie Downer, just suggesting some things to consider.

I would agree that for your first trip focus on the Big Three - Rome, Florence and Venice, and do day trips from each base. With a full three weeks you can certainly add the Amalfi Coast and nearby sites such as Pompeii.

in your original post - Welcome to the Forums, by the way, you'll get loads of help here - you said

I am interested in seeing the off the beaten path places, and interested in the culture, small towns/villages and less touristy areas if possible

but then your list was of many the exact opposite, then folks suggested for a first trip (my first trip got me hooked and I've been back many times) to consider the big three, which I agree with.

How does that sit with you off the beaten path, small villages, less touristy?

How do you feel about that?

Hi Susan & welcome to the forum!

I absolutely love Italy & have now stayed in 49 Italian cities. I could give you some itinerary options, but seeing your list of wishes, I really think the best option would be to take the Rick Steves 17-day Best of Italy tour. My husband & I took that back in 2006, and I’ve travelled to Italy subsequently 9 more times. But that tour was the foundational springboard to acquaint me with such a nice variety of Italian experiences and how to navigate the country with ease.

The tours have lots of free time; you’re not walking around following an umbrella leader. : ). And the extra unique experiences in the tour are so much fun, plus lots of great food.

If that’s something that interests you, reply and I can give you some nice options to either do your extra week before the tour or after the tour. By the way, I’ve never needed to rent a car in Italy (travel by train), but you’re welcome to do it.

(Personally, I wouldn’t steer you towards just the Top 3 & Amalfi. You recognize value in a less crowded experience.)

You need to be more realistic about you plans. You have enough in your plate to keep you there for 3 months not 3 weeks.
My two cents.
ROME
You need a minimum of 4 nights in Rome to see everything in your plans with comfort. If you also want to add Pompeii on a day trip from Rome, then you need to add a 5th night. It will take you about 2.5-3 hours and 2 trains (each way) to go from Rome to Pompeii (via Naples). If you fly out of Rome, then leave Rome as your last destination (like your last 4 or 5 nights of your trip).
TUSCANY
If you are interested in the villages of Tuscany, they are located between Rome and Florence. Renting a car for this portion is more efficient, however a car is a hassle in Rome or Florence, therefore you should rent it as you leave Rome and, after visiting the villages, return it in Florence as soon as you arrive. You would need to find a base (maybe in or near Siena) and visit places from that central base. If staying in Siena choose accommodations accessible by car and with parking available. Siena has traffic restrictions in the historical core. 4 nights would be the minimum I would stay for this driving portion of your trip.
FLORENCE
No car advised. Basically cars aren’t allowed in the historical center. You need at least 3 nights for the basics of Florence alone. From Florence you can comfortable visit Pisa and Lucca by train (even both on the same day). In that case add another night for that day trip.
CINQUE TERRE
Train from Florence is the best option, but it requires a couple of trains and 2.5 hours travel at least, so it is best to spend at least a night or two there, although some do it in a rushed day trip from Florence. Don’t drive there. The train is best, just as fast, and parking not that great.
VENICE
At least a minimum of 3 nights would be ideal. The fast train from Florence is the best way to get there. No car needed of course, cars can’t float.
LAKE COMO
It’s north of Milan. Best way to reach is by train (via Milan from Venice). 3 nights would be also ideal. Varenna, Bellagio, or Menaggio are the best towns in the Midlake and only minutes from one another via ferry.
PIEMONTE
I think you should leave this one for another trip, we are running out of days if the limit is 3 weeks. Also this is another place where a car is useful.
Rather than Piemonte, if you have a few nights left, I would expand on the areas you are already visiting. For example from Venice you could visit Padua or Verona. Bologna is also a place to consider only 40 min from Florence by train. Pompeii is near Naples and the Amalfi coast. If you stay in Sorrento a few nights instead of doing a day trip from Rome, you can see that entire area instead.

None of the places you intend to visit are off the beaten track. They are packed with tourists, especially from April to October.

I agree with the focus on the "big three." On my first visit to Italy twenty-five years ago, I did Venice (3 days), Florence (3 days), and Rome (5 days) by train. I didn't add day trips outside the cities, partly because I was a broke student but also because there's so much to do in the cities themselves! All the other spots you mention are wonderful, but you don't want to do them a disservice by rushing through them.

I had trouble this month bookings rooms in Italy for April in Rome, Bologna and Venice. Of course my budget of €150 maximum maximum may be a good deal lower than yours. So I urge you to start booking your hotels right away (I only booked with free cancellations). I believe May is a more popular time for tourists.

As for driving in Italy, I refer you to my trip report. I had driven trouble-free in Sicily and the Amalfi Coast as well as other European countries, but Tuscany and Umbria were trial and tribulation. A few other posters added their experiences too.

Since this is your first trip, I recommend the "big 3", that is, Venice, Florence, and Rome. And I would fly into Venice and home from Rome. You have enough time to do side trips from each of them. Venice needs at least 3 days, especially if you go to Murano and Burano. You could then train to Cinque Terre for a couple of days. Train to Florence a few days, get a car to visit more of Tuscany (do not drive in Florence!). Return car and train to Rome for remainder of your time, including the side trips.
Also, get your hotel rooms ASAP. I am also going in May, and booked mine last July and found slim pickings, but could be the type of places I wanted :)