Italy in April need help with Itinerary!

Cut out Rome save for another trip. It is too far from your departure port Milan.

Sounds like a great trip! You have mentioned six areas - Milan, Lake Como, Venice, Florence, CT, Rome. They are all great, but you won't have time for all. For me, I would pick Venice, Rome, and CT, even though they are spread out. But that's just me - I'm not an art / museum lover, and everybody will have different priorities. Suggest you read Rick's Italy book and decide which 3 are your top picks. Any 3 of the six will work, since the trains are so fast and easy. Also consider weather, especially if going in early April, the northern spots (e.g. Lake Como) may be cool or rainy. Enjoy your trip!

To save packing up and moving from hotels every other night, I would pick 2 home base towns and do day trips from there. High speed trains are frequent and can be very inexpensive if booked ahead. For example, if you stayed in Florence, you could see Venice as a day trip and then explore one of the many beautiful hill towns in another day trip. Rome also makes a great home base as there is just so much to see and do there. Have a great trip!

I would agree with the person who said leave a Rome out. It’s probably tied (with Paris) as my favorite city in the world but, if you’re flying in and out of Milan, I’d leave it for next trip to Italy (and yes, you will want to return!). While there is plenty to see west of Milan- in the Piedmont region- I’d also leave that for another time. With nine days I’d look at exploring from Milan to the east, with Florence being the southernmost city of that swath. Are you planning to travel by train or rent a car? For this trip, I’d suggest train.
I would go from your arrival in Malpensa into Milano for your first day and night. Assuming you’re arriving in the morning, take bus or train in and check in (or leave your bags if too soon for check-in) to your hotel. I’d spend time taking in the Duomo, the Galleria, possibly seeing DaVincis Last Supper (advance reservations required, follow Rick Steves). Since you’ve never been to a Europe trust me to keep moving OUTDOORS that first day - if you’re really tired take an hours nap in the afternoon but not more or you’ll not adjust to the time change. Have dinner on the early side (by Italian standards), about 7:30 but don’t go to bed before 9:30-10:00. After an overnight in Milano, you could take the train to Florence where I’d stay 3-4 nights - spend at least two days exploring Florence (follow Ricks advice, especially making reservations for the Uffizi Gallery and the Accademia/David), and one day for a day trip to Lucca (from which you can also take a less than one hour jaunt by bus or train to Pisa if you’re wanting to see the Leaning Tower - again, follow Rick’s advice). Train to Venice and spend two nights in Venice. It’s fairly expensive to stay IN Venice but worth it because most of the tourists will be gone in the evening and early morning when it’s most magical.
After Venice, many great options nearby. I would consider Padua, a beautiful small city with the Cathedral of St. Anthony (many people go there to touch his tomb). Also Verona is beautiful. As you suggested possibly a night or two in Lake Como as you head back to Milan (although, as someone pointed out, it might be a bit cold there in April). Still, Lake Como is beautiful - Hotel Milano in Varenna is a very good value in a beautiful spot.
Final advice, again to quote Rick: PACK LIGHT. If you can manage with a carry on suitcase, great. Otherwise take a SMALL checked suitcase and day bag you can sling over your shoulder - no more. Train travel in Italy is no fun with a lot of heavy luggage - trust me!

Take the train or bus from Malpensa to Milano Centrale train station. Take the train to Venezia S. Lucia (Venice) for 2-3 nights. Take the train to Firenze SMN (Florence) for 3-4 nights, train to Lake Como for the end. I haven't been to Lake Como so I'm not sure of the trains or if it's convenient to Malpensa. You say 9 days, so I'm assuming 8 nights in Italy, morning arrival. Make sure you have enough time to get to Malpensa for your flight home. Allow for traffic and 3 hours at the airport.

The Cinque Terre are more out of the way than Venice and if the weather isn't good, it's not enjoyable. If you are traveling around Easter, check for closures of sights, shops, etc.

Unless you want your trip a mad dash from place to place I suggest you narrow down the number of locations. Venice, Florence, Lake Como is a good variety and fairly compact geographically to accommodate your flights in/out of Milan

With your limited time trying to do both CT and Lake Como is probably not the best idea.

My first thought was 'way too many places' and I still think that. I was going to suggest just two bases with day trips but a few years ago I took a trip about that length with a friend who had never been to Italy and we ended up doing the 'classic Venice, Florence, Rome' and loved it. But the only reason it worked well was because I had been to all those places, some of them very recently and knew the cities, even the hotels we stayed in. That saved enormous amounts of time over someone (like you) who have never been. Just getting oriented, finding the hotels, figuring out the transportation, etc. That takes a huge amount of time and people who try to do too much on a first trip often end up not really enjoying it at all.

So my first suggestion would be to really cut it back. Take the train on arrival day to Florence and spend 4 or 5 nights and plan some day trips - to Siena (easy by bus) and to Pisa/Lucca (easy to do both in one day, by train). You could also take an organized day tour to some smaller Tuscan villages (hard to do on your own without a car but there are tons of group tours you can join for a day). Some people do go to the Cinque Terre as a day trip from Florence but I don't encourage it - too far and in April weather too unpredictable. But if it's very important to you and you get a good day weather wise it is possible. Then go back to Milan for the rest of the trip and do more day trips. You can easily do Lake Como, Lake Lugano (switzerland), Bergamo, Pavia. All very easy by train and all make great day trips. This way you have only two bases (hotels) and you can take or not take the day trips once you are there when you see what you feel like - and also depending on weather. That is what I would do if I were you.

On the other hand, if you are really set on Venice and Rome, and you are really energetic, and have a good grasp of public transportation and traveling - then you could do this - head to Venice, spend 2 nights, then Florence, spend 3, then Rome for 3 and back to Milan for the last night. You will only get the briefest look at each place and to get anything at all out of the trip you need to spend a LOT of time before you go researching what you want to see, mapping it out, etc. But here is my trip report on that fast paced trip I took a couple years ago - https://andiamo.zenfolio.com/blog/2017/5/italy-through-fresh-eyes---chashing-the-sun-in-italy-in-march

Chani has given you a very realistic plan for the time you have. She is a wise and experienced traveler. You accnot do it all, so do a small portion well and plan to return.

I agree with Chani. Good advice. You will be able to see a lot using public transportation. It is easy to negotiate Milan to Lake Como.
It is a beautiful area, unfortunately the 3 days we spent were rainy.

Thank you all for the great advice and recommendations! :)

I would go straight to Venice for 2-3 nights. Then Florence, maybe 3-4 nights and you can do day trips. You can still go to Lake Como, most people recommend Varenna, for a couple of nights. Depending on what time your flight leaves Milan, you probably want to spend the night there before you leave, to be safe.