Suggestions for Italy itinerary

Sean, can I assume you've already booked the plane tickets? If not, it would save some time to do an open jaw flight into Venice out of Milan. Sometimes it costs the same or less than a round trip ticket.

But, if you are committed to Milan round trip, one suggestion might be to train directly from Milan to Venice the day you arrive and put all of your days in Milan together at the end instead of splitting them up. Some flights into Milan get in very early anyway, so by the time the train would get into Venice, it might be lunch time or even earlier. (If your flight into Milan is later in the day, then my suggestion to start in Venice makes a lot less sense.)

Otherwise...how much time to spend in various places is a bit of personal preference. Mine is that I wasn't crazy about Milan - one night there was plenty for me. On the other hand, I loved the Italian Riviera, of which the Cinque Terre is one part. So I'd be inclined to spend a little more time there with three weeks, especially if this were my second trip to Italy. You could see more in the Riviera than Monterosso e.g. towns like Camogli or Rapallo that are further north closer to Genoa. They may be a little more touristy in June than outside of summer, but I'd expect Monterosso and all of the CT (which I have visited a few times and still love) to be mobbed with tourists more than the other towns, at least with American tourists.

Venice is truly unique and amazing and I'd want at least a few nights there on a first trip.

I haven't been to Lake Como so can't help you there.

Perhaps you can propose an itinerary with your guess of nights allocated and folks can comment on that specific itinerary.

Since you will be there in June, any interest in attending the Jousting Festival in Arezzo if your dates line up? Then it’s 1 1/2 hours to Assisi by train.

1 night in Assisi seems short, especially since it’s a bit of an outlier. I would try to stay there two nights.

For minimums - I would give Venice three nights, Lake Como two nights, Monterosso two nights, and personally I haven’t been a fan of Milan compared to all of the other options available.

Thanks for the suggestions so far. Our flights are already booked, and round trip to Milan was the best option that I could find for us in June.

I really like the suggestion about the Riviera, and I've started reading more about all of the beautiful towns in that area. Now I'm thinking of spending 5 nights in the Riviera, and I'm wondering, can we stay in one town and easily visit the surrounding towns? Or would it be better to check in and check out of a couple different towns. Based on what I've read so far, it could be great to see Camogli, Portofino, Santa Margherita Ligure, Monterosso, Levanto, Porto Venere, etc. What do you suggest in terms of picking one town as a base, versus staying in a couple spots?

Overall itinerary is looking like:
Milan - 3 nights;
Riviera / CT - 5 nights;
Florence - 5 nights, but possibly use 2 of those nights to visit Assisi;
Venice - 4 nights;
Varenna (Lake Como, Bellagio) - 4 nights;

All suggestions are welcome, thanks!

Sean, whether you'd be more comfortable staying in one riviera town the whole time vs. splitting up your time in two nights is largely a personal preference. My inclination has been to split my nights, but some people prefer not moving so often. One thing great about the riviera is that the trains are super convenient to connect most of the towns, from Genoa all the way down to La Spezia. (Some towns like Camogli may have more limited train service - some faster trains don't stop there but plenty of regional trains do.) Picking which individual town is also more down to preference (though I know, without having been there, you may not know the difference). I've stayed in Camogli and Rapallo. Both are nice but I slightly preferred little Camogli. Santa Margherita Ligure though is a really lovely town too. It feels slightly more touristy the others, a little bigger maybe? But it wouldn't be a mistake to stay there.

There is ferry service around the Portofino peninsula (Rapallo, Santa Margherita Ligure, Portofino, Camogli) plus you can hike between some of the towns (though less rewarding, than the Cinque Terre trails, MUCH less crowded!). It's easy to hike between Rapallo, Santa Margherita Ligure, and Portofino. You can hike between Portofino and Camogli too but more difficult.

It's hard to pick a bad Cinque Terre town, either. (They are worth seeing.) I have an affection for Levanto because I've stayed there a few times as a budget solo traveler. It's a nice town, but...it's not quite the same as the five villages of the Cinque Terre that eye-pop out of the side of the hill in such a dramatic way. Levanto is a nice town but seems more of a conventional beach town. You can hike from Levanto down to Monterosso too (hike is OK but when you get to the point just above Monterosso, BREATHTAKING view south of all five CT villages!).

Vernazza is Rick Steves's favorite CT town so seems the most crowded of the five. Manarola is the smallest. Corniglia is high up on a hill, ferries don't stop there, and you have to hike up to the town from the train station, so it's less popular at night I'd say...which might be a big benefit. None of the towns is likely to be super crowded at night anyway, though.

Thanks Andrew. Great suggestions. I'm leaning towards 2 places to stay in the Riviera; one in either Rapallo or Santa Margherita Ligure-Portofino. Seems like it should be easy to take a train there from Milan. Explore that part for 2-3 days, then scoot down closer to CT. Perhaps stay in Levanto or La Spezia for 2-3 days. Seems like it would be easy to visit the CT towns from there. And also easy to take a train on to Florence when our time in the Riviera is over. I might even stop for an afternoon in Lucca on the way to Florence.

I'm assuming for these shorter train rides it isn't necessary to but tickets in advance. Probably not much cost savings and then we'll have flexibility to see whichever town we want each day.

Separate question: have you been to Volterra? I'm wondering if it is similar to Sienna or San Gimi; and if it is worth a day trip.

Also, I've heard some good things about Ferrara; maybe we should stop there on the way from Florence to Venice.

So many places to see...

I haven't really spent time in La Spezia, but between the two I would probably prefer Levanto I believe given feedback I've heard (and because I know I like Levanto). E.g. you have one easy hiking option from there down to Monterosso.

In Italy, the regional trains don't have discounts at all - they are the same price the day of departure as they are in advance. (Most "short trains" are probably regional - but if it's an IC train or Eurostar it's going to be cheaper in advance most likely, no matter short it happens to be.) So yes, I would not buy regional tickets in advance. There is a hiking/train pass that covers all of the Cinque Terre including La Spezia and Levanto (regional trains only) so keep that in mind also; if you will be hiking the main trails between Cinque Terre towns, you might wind up buying that pass so need no extra train tickets for those days in that region.

On one trip, I kind of winged it and didn't make plans far in advance and by the time I needed to train from Venice all the way to the riviera, the fast trains were all really expensive. But it was possible to take regional trains all the way across, because there was no penalty to book those at the last minute. It was not really much longer than the fast trains and probably saved me about fifty euros. Had I booked weeks or months in advance, the faster trains would have been cheaper and faster too.

I haven't bee to Volterra - but I'm sure others here have and can comment. Lucca is a nice town many people love.

I have been to Ferrara. It is a really nice town.