Italy advice

Any shared broader goals aside from this North-South split? i.e. shared primary focus on beaches, nature, food?

At that time of year especially, you can’t go wrong with either choice tbh.

I’m biased but from Rome going North will give you more variety, versatility and greatest hits stops, e.g.:

Rome > Florence + Siena > Bologna (if you go North don’t miss it, it’s one of premier foodie cities in Italy and the world) > Lake Garda (Sirmione) OR Cinque Terre/Portofino et al for seaside getaway in the North > Verona > Venice


If you go South I and want beachy vibes I recommend Puglia (Polignano a Mare) over Amalfi for lesser crowds and lower costs (or if you really are into the beach vibes go to Sardegna).

What Purple said.

It will be very hot in late June. If you go south, stay near water. It will be warm in the north, too, but not as bad. I can't imagine how incredibly crowded the Amalfi coast will be in late June. The Cinque Terre won't exactly be barren but it offers a similar experience in a less crowded environment. In fact, the further north you go up the coast, the better. Riomaggiore will be impossible to navigate due to crowds. Monterosso al Mare will be far less packed but it is beautiful, as well.

One last thing...I want to plug Florence. It is my favorite city on the planet. More history than you could ever absorb, less busy than Rome, cleaner than Naples or Venice, and tons of shopping for the women if they like that. My wife and daughters loved the custom leather work that can be found all over Florence. They each bought multiple purses. Anyhow, Tuscany, overall, is fantastic. Lucca is absolutely worth a day or two. So is Siena.

Wherever y'all go, you will have memories for a lifetime.

Following, planning on going in 2026 (Rome-Venice-Milan-Como) over 10ish days in May.

I have taken some version of both of those trips several times. They are both spectacular. You can’t go wrong either way.

If you have never been to Italy, I would pick the northern route first One time we went to Rome for a few days then got a rental car and drove to Tuscany for a week then turned the car in in Venice, stayed there for a few days and flew home.
We stayed at a villa just south of Florence and did Florence as a day trip. Also did the Cinque Terre, Lucca and Pisa as day trips.

Another time we flew into Florence, got a car and spent the week at the same villa, then spent three more days in Florence before taking the train to Venice.

A few years ago we flew into Naples and got a driver for the hour long drive to Positano. We spent a week in Positano from where we explored the Amalfi Coast by ferry. Then we took the train from Naples to Rome.

I would not hesitate to do any of these again.