5 or 6 weeks to tour Italy

I think it may be best if you read a guide book and put together an itinerary. There are many different options here, its like us trying to predict the lottery numbers for you.

I would recommend you find a "base area" for each week. Then plan trips from that.

Also figure where you want to fly into and out of. You should consider flying in and out of different cities.

For our 4 week tour earlier this year, we chose the following as bases

Varenna - Lake Como
Verona (Quick Stop)
Venice
Florence
Salerno
Rome

However what I did was catered for my family, with many side trips.

Again, you have many options. Have a go at putting together an itinerary and check here for validation.
Grab a book and get reading..

I've been traveling to Italy since 1970, and we've been there the last 3 years. I never get tired of Italy, but the big cities and the most popular tourist sites are just too crowded in high season. There are plenty of places off the beaten path that suit our needs.

I have been to most tourist sights in Italy and I would have difficulty visiting Italy (or any other country) for 5-6 weeks. I'd like to spend time in Lake Como area, Tuscany south of Florence and the Amalfi Coast.

Otherwise, I'd prefer to go places we've never been to--like Slovenia which is a short bus ride from Venice. And I'd like to return to Croatia and Montenegro that we adored. I also never get tired of Budapest.

Note: I'm not a Naples fan, and we don't care to return to Pisa

Venice, Verona, Ravenna, Pisa, Sienna, Orvieto, Capri, Amalfi Coast, Sorrento, Pompeii/

Be sure to spend several days in Rome, lots to see there.

Start south and work north to maximize your chances of good weather. April could be cool and wet in the north and early June could be hot in the south. If money is an issue, it would be smart to take a look at lodging rates on booking.com as you begin to organize your itinerary. I don't know when the big fashion events take place in Milan, but I bet they drive up hotel rates significantly.

I always say Sicily alone needs about 2 weeks if you're willing to rent a car for part of the time; add a few days if it must all be done by public transportation. So, though 5 or 6 weeks seems like a long trip, a solid visit to Sicily could leave you pinched for time on the mainland. A week wasn't long enough for me in Naples, and I still have places to go (including St. Peter's!) after 20 days in Rome. But I spend a lot of time wandering neighborhoods in addition to going to specific tourist sights, so I always spend a lot more time than average in the larger cities.

An add to my post for all, thanks for the replies. This is a one time and done trip to Italy so yes some of the “tourist” places are a must. Because of financial constraints, at this time to my knowledge, this trip will be it. Because of budget I shall use Monastery Stays as much as possible with maybe, if I can find a reasonable hotel or airbnb in the mix..

Someone in a recent thread said it's best to book stays at convents and monasteries directly rather than through the Monastery stays website.

There’s the thread about monastery stays https://community.ricksteves.com/travel-forum/tourist-scams/monasterystays

As for an itinerary, get a guidebook AND a map. Lay out a route you want to travel and where you want to go. Then use the guidebook, websites and forum to fill in the blanks as to what to see and do.
Write out your itinerary. Make a list of “A” sights, then “B” and “C”. Just because I want to see something, you may not want to.

Admit you can’t see and do it all. Give yourself time to relax and enjoy your time in Italy. Remember that every time you change location, you lose at least half a day checking out of the hotel, transport to the new town, checking in to the new hotel, getting oriented.

I travel on a fairly tight budget. Make a budget. Keep it flexible. Good chance you will add things on the trip to see and do. You don’t want to miss something you really want to see if you worry about nickels and dimes. Sometimes it’s a trade off. I stay in cheaper hotels and eat in cheaper restaurants so I can afford concerts, exhibits and museums.

Are you traveling solo? I find that food tours break the loneliness of eating alone. https://www.eatingeurope.com/
I add a Rick Steves tour in the middle of my trip. I try to use it as a way to see places the may be difficult to go to on my own. Example: next September I start in Venice solo for 5 days; go on the Village Italy tour to see Tuscany and hill towns; then solo 4 days in Florence; ending in Rome for 5 days.

Take trains instead of renting a car. Trenitalia will get you most places. https://www.trenitalia.com/en.html
Day trips can get you to out of the way places.

There are city tours that work for tips. GuruWalks is an example. https://www.guruwalk.com/. Use the city walks in Rick Steves guidebooks or on his app for free.

Have you traveled to Europe before? After you do your research, ask lots of questions. Many things have changed over the years.