Please help with Italy itinerary for 3 weeks in June 2022

A very busy itinerary, but doable. However I think youre making the usual mistake of first timers in trying to see too many places in the time available. You've really given yourself no down time and may find yourself hitting the wall before the end. I'll offer the advice that is often given - choose either the CT OR the AC, not both. They're both seaside areas. Personally I'd choose the AC as there are more things to see and do there (and the CT will be inundated with thousands of cruise ship passengers just about every day). Allocate those extra days to some of your other cities. You could use them to relax in Positano, possibly.

Seven hotel changes (plus 4 day trips ) in 21 days sounds exhausting. But when I was younger I used to travel like I was on the Amazing Race. Now I’m old(er) and enjoy a slower pace (and fewer museums!)

Do you have to travel in June, since you don’t have kids? If so, I would go as early as possible to beat the heat and crowds. If you could go in May, the trip would probably feel very different.

You can travel with kids, so don’t think of this as your only chance to see “everything”. This may be your last chance to travel leisurely without kids!

Had you considered stopping at Pisa on the day you transfer to CT, rather than making a separate trip to/from Pisa?

That would free up a day to use for something else or add a day somewhere else.

That's my thought. Use it ( ignore it) as you see fit.

My fiancée (now husband) and I did a similar trip to Italy before we got married and had a kid. I wanted to make sure he could hang with my travel style haha. This is an ambitious itinerary, but looks perfectly reasonable for two young adults looking to go-go-go.

Our kiddo just turned 5 and he's been to Europe on three separate trips (five if you count the two trips we took while I was pregnant), and we're going to Italy for two months this summer. So traveling with kids (even young toddlers) is totally doable, but it IS different. Mainly in the amount of time you will have for museums and art galleries, plus the overall ease of travel.

So, I will advise that if you're museum people, to prioritize the big cities (Venice, Florence, Rome) where there are a lot of indoor, adult-focused sights. If/when you go back with kid(s), it's going to be harder to see things like the Palazzo Ducale, Uffizi, Vatican, and other blockbuster museums. Places like Lake Como, CT, and the Amalfi Coast are more laid back and will be easier to do later with kid(s).

Personally, I would keep Lake Como and eliminate Cinque Cinque but I have to admit I haven’t been to Cinque Terre. We chose last summer to go to Lake Como over Cinque Terre. I think there is more to do there with the lovely gardens and there are numerous hikes you can do as well. It also isn’t as crowded. To me there is nothing like the view of a lake with mountains in the background.

That said, here are a couple other thoughts I had. If you keep Lake Como consider going there upon arrival. You can take the train into Milan and then transfer to a local train to Varenna which is on Lake Como. It is nicer to get over jet lag outdoors and good to travel further on arrival day . We did this but stopped in Milan on the way to see the duomo (left our luggage in the train station). The other advantage is you can get to Venice quicker from Milan. We ended up with a fair layover in Milan coming from Lake Como.

It would be much faster to get to Rome from Florence than Cinque Terre.

The other suggestion I had is to stay in Positano and visit Capri from there. We did that and left our luggage near where the ferry docked. We then took the ferry to Naples where we spent the night before flying out the next morning.

If you include the Cinque Terre skip the Amalfi Coast. We went to Italy many times before he headed south of Rome.
Italy will be there when you want to plan another trip. Do not plan too many locations as it will be a blur.

I agree with the poster who said to skip the Cinque Terre and go to Lago di Como. And the idea to go straight there instead of staying in Milan is also a good idea.

I've been to all those places you listed, and Cinque Terre is my least favourite. It's fine, but the Amalfi Coast and Lago di Como are much nicer and there's more to do.

For your day trip to Pisa from Florence, go via Lucca. Buy a picnic lunch and stop somewhere on the walls to eat it. You can walk the walls, or rent bikes and ride around on top of them. Then go on to Pisa to see the tower and duomo.

Have fun! We traveled Europe before kids, and then took them when they were babies, young children, and teenagers. Now my oldest daughter lives there, so I always have a reason to go back.

I can vouch for the fact that your itinerary is entirely manageable, because I did an almost identical trip with my wife ten years ago- and we were already retirees by then. We spent 24 nights on the ground, and stayed in each of the cities and towns in your plans (Varenna on Como and Riomaggiore in the CT), except for Naples. We also spent a full week in one agroturismo in Tuscany, so in fact covered the rest in 17 nights. Yeah, it was busy, and our preference now is a slower pace, but we thoroughly enjoyed every stop we made, and we’re glad we got to see them all. That being said, I would agree that the CT may be expendable, as it will be very busy, and is, I think, overrated. I found the Amalfi coast to be just as beautiful, and there are great hikes that can be done there as well. If you are travelling by train (we did it all by train), it is essential that you follow Rick’s Rule and TRAVEL LIGHT.

I would say flying into Venice first, then Milan -> Lake Como -> CT -> Florence and so on. It would save you some redundant trips on train.

Looks like a great trip. However, even considering you are both young and it being your first trip, it doesn't give you much time to really soak in the places where you are going. I agree with the suggestion to drop Cinque Terre and add elsewhere---for me it would be Positano since you are headed that way. At that point in your trip you might be ready to have some down time. Maybe do some hiking on the Path of the Gods, visit a mozzarella farm and just do some fun stuff. Between Ravello, Amalfi town and Positano you can easily spend 2 days.

It will be your first trip of many.

Enjoy!

From Malpensa airport you can take a direct train to Milan’s central station and hop on a direct train to Varenna (1h 15m) and sleep there your first two nights.
When you’re ready to go to Venice you’ll need to connect in Milan so leave your luggage at the station and see what you want to see in Milan before going to Venice.
I agree with Joe and would stop in Pisa on the way to the Cinque Terre. It’s possible you’ll have to connect there anyway and you can lock your bags in a locker while you sightsee.
If you’re going to the Amalfi Coast you will not see it while staying in Sorrento. I suggest taking a bus to Positano if sleeping in Sorrento and a ferry back. If you spend a couple nights in Positano you can take a bus to Amalfi and a ferry back to Positano. You can then take a bus to Salerno and a direct train to Naples.

Less, Less, Less!
Extend all the times in each of the major stops (Milan, Venice, Rome, Venice) which result in the loss of one. Add a smaller town in Tuscany . Leave something to come back to. 33% of your trip is moving from point A to B. Can be exhausting. More is less. Enjoy your trip.

Thank you so much for your help everyone! It's really appreciated and was very insightful.
We have decided to head straight to Lake Como for a few nights once we arrive, cut our Cinque Terre so we can spend more nights in Florence, Rome and the Amalfi Coast :)

Just to add, as another poster suggested, with your changes you can easily spend the day in Milan en route from Lake Como and Venice. I did that going from Lake Como to Florence. Take an early train to Milan, leave your luggage at the station, and you'll get to the cathedral just after it opens, which avoids waiting in line. You'll have time to see a few other sites as well as the Last Supper (if you can get a reservation), and then continue to Venice in the mid-afternoon.

I understand wanting to check Capri off the list. Blue Grotto was cool but island was very crowded in June with lots of high end shopping. We MUCH prefer Ischia, another island nearby. You can take a little bus around the island. There are many places with thermal pools. Not nearly so crowded as Capri. One of our favorite places in Italy.