I'm planning a trip to Italy...any opinions on how to best spend a week there? (no rush)

Not sure why you keep adding Milan in the must see bracket - it’s mostly a business city. Doesn’t have anywhere near the attractions or charm of Rome, Florence and Venice. I’d drop that from your list.

Note that most of Italy is pretty much tourist heavy, so I wouldn’t worry too much about that. Rome will likely be very hot, so you might want to skip there.

Hot so I recommend Lake Como, Lake Garda (wonderful ferry rides around the lake stopping for wine, cheeses, breads, snacks then back on the next ferry - rinse/repeat. Verona is nearby. Amalfi coast with the small villages crammed by the sea connected by a rail line. Eat light and often. I’d skip Milan and Rome.

Florence was definitely our favorite. Milan had a couple of good attractions (like The Last Supper) but we found it very similar to New York City.

Moved from The Café to IMHO.

This point is very important. If you’re visiting big sites in Rome or Florence, you can often pre-purchase tickets online and skip the looooong queues (eg Vatican Museum, Uffizi).

So, let’s get down to details. What are you interested in? How do you like to spend your vacation? What is the romantic vision you have of Italy that you want to tick off (eg driving the Amalfi coast, taking a boat across an Italian Lake, gazing upon vineyards and cyprus trees in Tuscany, wondering through the back streets of an ancient village on your way to a cozy trattoria, catching an opera, going wine tasting, visitng a monastery) - if you can give us a bit more of what’s in your head and heart, we can help you plan a route. BTW a week isn’t very long at all, so dial back your ambitions a bit. And don’t just do cities - Italy is vastly more besides.

Oh, and where’s the wedding?

The lakes are lovely, I preferred Garda to Como.
Verona is nice, I enjoyed my weekend in Pisa and Lucca. Milan is fine but I wouldn’t rush back.
Top of my list will always be Rome, I think it is a fabulous, dirty, busy hot mess with a billion things to see and a treasure round every corner on any random walk.
One gem that can be reached by a commuter train from Rome is “Ostia Antica” which is the old abandoned port west of the city. It has the benefit of being peaceful compared to Rome.
A close second would be Pompeii and Herculaneum. The former is the single most exciting site that I’ve ever visited and the latter not far behind (I’ve been twice to both)
Our last trip had us flying into Naples, staying in Sorrento and then getting the train up to Rome and flying home from there. The trains are excellent. Apparently they run on time.
My top tip for anyone staying in Sorrento (and sorry for mentioning this for the umpteenth time) is to eat at Porto Marina.

My wife and I had our honeymoon in Garda, and loved it. Wonderful part of the world.

My suggestion would be a trip into the Dolomite mountains. They’re in Italy, but the area is historically Austrian and it feels completely different to other parts of Italy. We went up the Sass Pordoi mountain in a cable car, and it was amazing (as long as you’re OK with heights). There’s a restaurant at the top, and some of the most stunning views you’ll find anywhere. I expect you’ll find coach tours that offer transport, cable car and a meal in the restaurant as a package.

I’d say pick one of the flagship cities, Florence or Rome (other one being Venice, but you’ve already been there) and build your trip around that. If you’re concerned about the heat, northern Italy in June shouldn’t be too hot. I’d expect Florence to be crowded, but it’s definitely worth a couple of days. After that, decide what you’re interested in. If it’s wine, Tuscany’s to the south. Siena and San Gimignano are both beautiful small Tuscan cities that are easy to get too, and give you access to the Tuscan villages if you want to see the countryside. (I haven’t been to San Gimignano myself, but know about its reputation.) If you like food, head north. Bologna’s beautiful and gives you access to Parma and Modena. You could do a day trip from Bologna to San Marino by taking a train to Rimini and then getting a bus, but I wouldn’t bother unless you want to add it to the list of countries you’ve visited. Or if you want the coast, head west to Pisa, see the sights and then start working your way north. If you like hiking, there’s a wonderful but hilly trail called the Cinque Terre. Also, some pretty nice seaside villages with small beaches.

Keep in mind that the events surrounding the wedding will likely take up a couple of days. Where is the wedding going to be? Knowing that would help identify what’s near enough to get to comfortably. Italy is smaller than the US, but not small. It’s easy to fall into the trap of non-US travelers going to the US and wanting to see too much, “I figure I’ll check out New York, then pop over to the Grand Canyon in the morning, and see San Francisco in the afternoon…”

The wedding is in Passignano sul Trasimeno (Umbria). But I am happy to zoom all over Italy before I arrive there.

As for the rest…I kinda like it all. By which I mean, I want to find a must-do list given a relatively short visit. I know I can come nowhere near seeing all the things in a week but, if this is my one and only ever visit to Italy (technically second but only saw Venice the last time), what is not to be missed?

Ok! So that gives us an end point. Are you flying home from Perugia? If we know where you’re flying back from, we can suggest an open jaw route which will maximise your stay.

I would not try to see multiple regions, but stick to Tuscany, Umbria, and Rome for the week. There’s really just not enough time to really enjoy these amazing places by rushing through them. You could easily spend a week in Rome alone.

Are you flying into Rome? If so, Vatican City is certainly worth a visit. If you’re going to be in on a Friday night, look for the summer tour hours of the Vatican museum on Friday evenings. It’s a way to see the wonders without huge hoards of people. St Peters Basilica is a great visit, buy a tour to save time waiting on line but you can wander around after. There’s so much in Rome that it’s hard to know what else to recommend for a brief visit.

It will be hot, so be prepared for that. Mid-day gelato is critical for survival.

I have not planned my visit yet.

Hopefully Covid won’t eff you all up. We’re not considering any plane travel until this shat is more cleared up.

My trip is not for a long time yet.

My experience of foreign travel and covid so far is that you’re pretty much ok if you stick to the summer months, when the infection rates seem to drop in tandem with most countries’ desire to save their tourist season.

Looks like that would make a very easy trip to Siena, and up to Florence, to start with. Then over to Pisa, if that floats your boat.

I strongly endorse this - these regions alone are stuffed to bursting with possibilities.

I would fly into Rome, and spend AT LEAST two days there. You’ll barely scratch the surface, but you can at least see the Vatican Museum and the Colisseum/Forum, and whatever else floats your boat. Everyone should see Rome at least once in their lifetime. Then train it to Florence for a couple of days (in my experience, Italophiles are strongly split about which of these two great cities they love the most - you’ll either be Team Rome or Team Florence for ever).

Then hire a car and wind your way to your wedding - you’ll have multiple options for iconic Tuscan and Umbrian towns and villages to explore - Arezzo, Cortona, Siena, Montepluciano, Montalcino if wine is your thing, San Gimigniano (obviously not all of these, just pick a couple en route) - by which time you’ve barely skimmed the surface, your week is up and you’ve arrived at the wedding.

I think getting a good soaking of Tuscany is ideal for someone who hasn’t seen much of Italy - the landscape and sites are truly memorable.

Having your own car gives you more flexibility and allows you to explore the amazing countryside and tucked away hill towns.

Fly home from whichever nearest airport goes your way (Perugia is the closest, but you could possibly fly out of Florence or Pisa. Maybe even Ancona. Rome at a push).

I’d say that Rome is a must-see, especially if you have any interest in historical stuff. I mean, it was the capital of the Roman Republic/Empire for about a thousand years, and then the center of the Catholic Church for two thousand years.

I’m definitely in Team Rome; Florence had great art museums, but that was 99% of what’s in Florence (I liked the Bargello the best, FWIW). Rome has art museums, cathedrals, historical ruins, historical cathedrals, and so on. And they’re on every block it seems.

Central Milan is cool enough when i got stuck there for 3 days waiting on a rescheduled plane flight during the 2010 European winter storm., but I’d have been disappointed had I actually gone their intentionally for tourist purposes.

We recently had reasons/opportunities to go to Italy twice in the space of a year (November 2018 and June 2019).

On the first trip, we were there to see our son, who was spending a semester studying in Florence. We spent the whole week in Florence and Rome and went to a fair bit of stuff in both cities. From Florence it’s easy to get to Sienna and Pisa. Pro tip: the Pisa airport is bigger than the one in Florence, so has more and cheaper flights, and is only 45 minutes by train from there. It’s also cheaper to fly to than Rome, though probably not Milan. There are museums in both cities that are very good but much less crowded than the more famous ones. For example, the Castel Sant’Angelo in Rome and the Hopital degli Innocenti in Florence are relatively quiet and have unbelievably wonderful rooftop views of their respective cities.

On the second trip, my parents were renting a place in Florence for 3 weeks, so we went for about 10 days, most of which we spent in Florence, but we spent the first couple of days on our own in the Cinque Terre. That is an amazing place. On the coast, it wasn’t extraordinarily hot in early June. Yes, it’s very tourist-packed, but if you hike the paths between the towns, you’ll get some relatively uncrowded vistas that are quite spectacular. We stayed in Levanto, which is north of the towns. It’s much quieter than the place most people stay to the south. The regional cuisine is anchored by pesto, anchovies (not just the salt-packed ones) and focaccia, which are 3 of my favorite foods, so I was really, really happy there. There’s a paved bike/pedestrian trail that runs north from Levanto along the water that is a rails-to-trails project that runs through old train tunnels (so has long stretches of shade). It’s just a 2 mile walk to the next town. Makes for a very easy, pleasant walk.

We have loved every moment we’ve spent in Italy, despite the crowds. Have fun!

PS: Never eat dinner in a restaurant that is serving food before 7PM–it’ll be a tourist place and will be mediocre. I wish I remembered the name of the place we ate the last time we were in Rome–it was recommended to us by a bookstore clerk we spent some time chatting with. I think we were the only native-English speakers there, I was bumping elbows with the guy at the next table, it was so intimate. We witnessed a group coming in where the host asked them over the crowd noise “Tre?” (3?), and they responded “Nove!” (9!). And he just shrugged and started moving chairs and tables around the already packed place. And the food was excellent, too.