90 Days in Italy

Sounds like a good problem to have.

What time of year is probably the most important question since their stay will span am entire season?
If they've never been to Italy what is their other European travel experience?
What are their main interests in travelling and staying places?
Do they speak any Italian?

And lastly I'm obligated to mention the importance of staying no more than 90 days in Schengen - including all travel days - assuming they are there on a tourist visa from somewhere like the states. The penalties for missing this number are very high.

Let everyone know because these are the details I would start with,
=Tod

Make sure they check out travel.state.gov for passport and medication information: https://travel.state.gov/content/travel/en/international-travel/International-Travel-Country-Information-Pages/Italy.html. When traveling more than 30 days within a country it’s best to follow the rules. To learn how much medication is allowed to bring into a country they may need to contact the embassies and consulate office.

I always give myself a handful of days for breathing room. All of a sudden a rail strike, or just anything unexpected, it’s not worth risking a violation of the 90 day restriction. Fines are ‘just’ money, however I want to be allowed to come back!

I have stayed in Italy for up to 7 months at once (I have citizenship which I mention only because I know the folks will question the allowed length)...Anyway, I usually plant myself in one town/city and go from there. Once, I did split my time over my 5 month stay to 3 months in a town near Florence, then a month in Genova and a month in Chiavari which was lovely but was not crazy about moving around so much and relocating. I like the benefit of staying put and getting to know the area and local culture. Being close to Florence was perfect for transportation for any day trips and I was close enough to the sea to be in Viareggio in about an hour. And visiting other areas is economical for weekend away....last year (only stayed 3 months) I visited Sicily for 5 days and flight plus hotels under 200 euro...bargains available w/Ryanair. What ever works for your friends tolerance for packing up and relocating as well as the time used up in the process. It will be a wonderful adventure either way! Enjoy.

Time of year is really critical here. So much of Italy (including Florence) is likely to be miserably hot in the summer.

First let me say: TAKE ME WITH YOU! Now that I have that out of my system, I do have some thoughts. They can do a lot of sightseeing in 90 days. But they can also do alot of cultural experiences in the same 90 days. By that I mean, besides seeing the main tourist sites, spending extra days in a location can be a wonderful experience. And some great places are great because there isn't that much to do there after a couple of days: Spello, Agrigento, Perugia, Assisi, Padova, Trieste, Viterbo . . . I could go on and on. These can be places where you feel like time has stopped. Maybe suggest they do 3 or 4 nights in those kind of places while spending a week or two in Venice, Florence (not if it's during the summer heat and humidity!), Rome, Sorrento, Ortygia, Palermo, Naples. With more time they can see lots of sites more than once - second or third time can be just as amazing. I'd also suggest VRBO apartments when possible. Much easier to unpack, do laundry, fix meals with great local produce, or just enjoy being in a neighborhood.

A few years ago we spent 31 days in Lucca and loved just fitting in with the locals, being recognized by merchants and restaurants. You can do some days trips by train or bus and we walked the walls every day. We had a great vrbo across from the music school and woke to music each morning.

"First let me say: TAKE ME WITH YOU! ......... Much easier to unpack, do laundry, fix meals with great local produce, or just enjoy being in a neighborhood."

Well....I am having lunch with them tomorrow and I have shared a bunch of my Italian adventures with them so their excited to get my advice, but I'm like "I have no idea what to do with 90 days!".

Thanks for your advice (and to everyone else as well). As far as dates, they will arrive in August and leave in October. I'm going to recommend they travel north to south over the course of their trip with their flight arriving in Venice and then likely leaving from either Rome or Naples. Would you encourage them to Hub out of Venice and cover the Veneto from there or would you spend a few nights and Venice and then hub our of Verona, Vicenza, or another?

Fly into Venice and out of Palermo.

There's a lot to unpack here.

Venice is not a good base to explore from because getting to the train station can be slow/difficult and you need to get to the mainland before you can even start to head to another city. Verona is a good choice but August is season there - operas in the Roman Arena and music in the old Roman Theater.

First off: Summer in Italy is both hot and high season. The idea of staying 3 different places for a month each becomes much harder in high season. Every place has its special days, conventions, festivals and so certain days are hard to book. And if your visit falls across that time you will be limited in what you can rent or it will be very expensive. Unless they are "money's no object" people mixing cities can help defray costs for what will be an expensive trip. Also because it is in season they should book ahead of time which will limit their flexibility but I wouldn't want to show up in Florence in September with no reservation and wing it trying to book a week plus.

I would advocate for breaking up the big cities and tourist sights with smaller and more out-of the-way towns. But smaller towns and really getting into conversations with Italians brings up the language barrier. English is relatively prevalent in hospitality in larger cities but can quickly diminish outside of those places. I remember one (older) study that surveyed Italians and 80% of them rated themselves as speaking "some English" but on 20% did when actually tested. Italians love to talk and they love it when people are really trying to learn the language but no understanding the simple conversations of people around you can be alienating after a while.

Anyway here is my 88 day blind swing at a schedule that mixes big cities, small towns, allows time for side trips and exploring.
It includes north south and some east, west as well.

Place (Alternate) Days
Venice 5
Verona 6
Malcesine 5
Bologna 7
Florence 10
Lerici (Chiavari) 7
Siena (Arezzo) 7
Cortona (Orvieto) 4
Perugia 7
Rome 10
Pescara 5
Bari 5
Naples (mixed with Salerno) 10

To be clear I'm not advocating they sit down and book this I'm just trying to illustrate what that many days spread between a bunch of different places might look like.

It sounds like they still have some large and fundamental questions to be answered but if they embrace it there's a real adventure to be had.

To them: Buona fortuna per la tua grande avventura,
=Tod