31 Days in Italy

My first impulse was to suggest more time in the Naples area because the transit is so good, and you can spend time in Naples, on an island, and on the Amalfi Coast. It's a nice way to cap off a lot of intensive sightseeing.
The Emilia-Romagna cities are easy by train, as is Milan-Lakes and Liguria.
Tuscan countryside is difficult without a car, but some kind of contrast with the large cities would be nice.

They are all busy at Easter but Rome will be impacted the most due to closure of St. Peter's due to services. My inclination though, is to say start in the south and end toward the north. That way you have a better chance of warmer -- but hopefully not hot -- weather in Naples and more warmth by the time you hit late April, but again not too hot, in Rome, Venice, and Florence.

Naples is pretty chaotic. Maybe you'd be better off in Sorrento or Salerno and day trip to Naples. Depends on what you want to do but most of us -- and most travelers to the area -- are drawn to the Amalfi Coast and Pompeii, easily reached from Sorrento. I'd gladly spend a springtime week in Sorrento.

Have you decided where to fly into the out of? That will certainly be a factor if already booked, but offhand I would say Sorrento (fly into Naples) for a week, then Rome, followed by Venice and finally Florence. Take your three or four remaining nights at Lake Como and fly out of Milan.

Siena is without a doubt Italy’s most beautiful city after Rome, Florence and Venice so if spending 31 days in Italy, I would spend 2 or 3 nights in Siena. I would add the other 2 or 3 nights to the Naples, Sorrento, Capri and Amalfi Coast area so you can see all of it without rushing through it.

Leave CT, Milan and the lakes for the next 31 day trip.

In 2015, we spent 3 nights in Bellagio on Lake Como and 3 nights in Milan.

This spring, we will be spending 4 nights in Naples and 2 nights in Pisciotta, which is on the Cilento coast about 2 hours south of Naples. Our itinerary coming up allows NO time for the Almalfi Coast or Capri; we will go to Ischia as a day trip from Naples. Our final plan also leaves out both Sorrento and Salerno. IMHO Valdelphia's suggestion of more time in Naples makes a lot of sense.

I mention our two 6 night itineraries (each were/are parts of longer trips) for the reason that I think you are trying to take on a lot should you try to do "5-days" in Milan (including one of the lakes, it seems) and "5 days" in Naples. ("5-days" presumably means 4 nights.)

As to Naples, we received some very thoughtful advice from a number of others, so I will share that, here: https://community.ricksteves.com/travel-forum/italy/naples-and-environs-suggestions-per-favore As you consider Naples and environs, the advice that I received may also serve you well.

Whichever one you choose - Naples and its southern Italy area or Milan and one or more of the lakes or other locations between Venice and Milan - you will have a great time. Do consider the weather in April - that could be the deciding factor.

Is this for 2024 or next year? If 2024, what city are you flying into and which city are you flying out of?

What are you interested in seeing and doing? I have stayed in 30 cities in Italy, but I need some info to give an intelligent recommendation tailored to your wishes.

Just a short example, but no idea about your interests.
Milan
- Milan Duomo
- Opera, ballet & concert events at La Scala:
https://www.teatroallascala.org/en/season/2023-2024/index.html
- Day trip from Milan to Bergamo to enjoy the gorgeous medieval Citta Alta portion of the city.
- Day trip to Cremona

Is this for 2024? If so, I think you may be staying where you find lodging. But perhaps you're talking about 2025?

We have not booked flights yet, doing that tonight or tomorrow. Based on what I’m hearing about the weather, I’m thinking about starting in Siena / Naples area by flying into Rome (much cheaper than Naples) and finishing in Venice and flying home from there. So something like:

3/27 thru 4/4 in Naples/Siena/Amalfi
4/5 thru 4/12 in Rome
4/13 thru 4/21 in Florence
4/22 thru 4/28 in Venice

We want to do another trip that’s more outdoors and hiking so maybe we’ll do the lakes, CT, the Alps and Milan on that trip.

Because I’m on a special whole foods plant based diet we are trying to stay in airbnbs for 5-7 nights at a time to make shopping and cooking a bit easier logistically but if we need to break up the time south of Rome into two shorter stints we’ll do that.

• in Siena / Naples area

Siena is near Florence, in Tuscany. Not easy to combine with Naples and Amalfi Coast. Maybe you meant Sorrento?

Garden128, I'm really curious- are you finding reasonably-priced lodging just two weeks away and during Easter/ Spring break?
Also, be careful with booking flights out of Venice. It's difficult to get to the airport for early morning flights.
Have a great trip and please report back.
Safe travels!

I just booked round trip from Denver into Venice on 3/26 and home from Rome on 4/28 for $618 round trip on British Airways.

I’m going Venice first because there is Fiesta San Marco that last week in April and there are no accommodations available but I found some ok options for the first week.

I’m doing this on the fly and winging it so hoping for the best! I need to check accommodations in more detail in the other cities but seems being in Venice proper might be the hardest ask.

Venice, Florence, and Rome are three places I would not particularly want to return to.

All the other options you mentioned are where I would enjoy the most - the Hill towns of Tuscany, the Italian lake, District, the Amalfi coast, or Sicily. Who’s the booty which includes bologna in Parma in Medina. There is a colorful Verina with its Roman Colosseum. There’s the German-speaking areas of Italy, such as Bozzano.

You can get to Naples in one hour on a high-speed train, but from there it’s fairly large amount of time to get to the islands or the Amalfi coast. You can transform the balls, and then take a ferry to one of the two nearby islands of Naples, or even a ferry all the way over to expensive Capri. If you try taking a ferry over there in the morning, you’ll just have a couple of hours for lunch and then have to take a ferry back to Naples. Otherwise you risk getting stuck overnight.

What I’ve usually done is taking a train to Sorrento, and then stopped at Pompeii or Herculaum along the way.

Naples itself is not very true to in my opinion. He feels a little dangerous and actually a lot of the restaurants are super cheap, probably the best food deals in all of Italy.

When booking an Airbnb in Venice, I’m being told I have to pay a tourist tax on cash upon arrival, is this normal?

Yes, hosts often do it this way, but some fold the tax into the room price --- we wish they would all do this, but I see why they don't.

However, here's some news from Airbnb: https://news.airbnb.com/airbnb-to-collect-and-remit-tourist-taxes-across-italy/

I see your itinerary has you in Venice 4/22 thru 4/28? The 25th- 28th fall into a pilot registration period for daily visitation access fees. If staying in a hotel, your hotel collects that fee but according to the website you're still required to register. Day-trippers register and pre-pay via the link on the same website.

See this recent thread on the subject:
https://community.ricksteves.com/travel-forum/italy/venice-tax-exemption

And:
https://cda.veneziaunica.it/en/access-fee

Apologies if you already knew about this!

I actually had to reverse the order so we’ll be in Venice 3/27 thru 4/3, and Rome from 4/21 thru 4/28