We flew to Milan, took a train to Venice (3 nights), train to Florence (2 nights), drove to Valais in Switzerland (2 nights) via Cinque Terre and back to Milan (2 nights) via Lake Maggiore. Here are my quick takeaways from the trip:
Venice - I read tons of reports saying Venice is horrible in the summer...and it turned out amazing. The weather wasn't too hot in July, canal didn't smell, crowds were bearable and birds on San Macro not too annoying. We didn't have a set plan and spent most of our time around San Macro square, deciding what to do in the order of which has the smallest line...and saw all the main attractions incl. island excursions in 2.5 days. Our smartest decision: get an unlimited vaporetto card. Things I'd do again: glass making exhibition on Murano island (amazing), coffee on San Marco with live music and just wander around & get lost.
Florence - hot and super crowded. Lines everywhere even with prepaid tickets. It's a beautiful city and Uffizi's artwork is unmatched, but I found its exterior and organization less impressive than Louvre, Hermitage, Met, etc. Florence didn't strike me as a city that you'd want to visit over and over like Paris unless you're an art lover. What I'd do again: prepay for Uffizi/Accademia tickets (official site worked fine) and get a tour of Uffizi (Rick's downloadable tour isn't bad). They overview Renaissance history in artwork (not just individual paintings) and focus on specific pieces so you're not overwhelmed.
Cinque Terre - great to relax after Florence. Super crowded but you don't feel the crowd as much. We drove there - big mistake even for someone who likes driving - you don't enjoy the view because the road is so difficult. If you are driving, park in Monterosso (Vernazza was impossible on a weekday). It's paid but safe, all the way down on the beach and 3 min from train. You can leave the car overnight. What I'd do again: not drive and do nothing - it's hard in Italy where you're always running around but Cinque Terre is a good place to calm down. Don't get anchovies (traditional dish on every menu) unless you really like salt...
Valais (Switzerland) - this was our first trip and what struck us, aside from the landscape, was the friendliness of the locals. We met friendly locals in every country, but elsewhere they help you on your way...and here they share their lives with you. We asked a local what their job is like and got an invitation to visit them at work. We asked where the store is only to get...I'm going in 20 min, come along? I tried to park in a tight spot next to a cafe only to find the owner get out and help...and get into a 2 hour long talk after. What I'd do again: stay in a small village B&B rather than major hotel (I picked a place by map instead of town name) and try to become Swiss - I've never met more willing locals.
Milan - nothing special if you've been to Europe before ex Duomo. I got the sense you go to Milan with a purpose (shopping, business, see Last Supper), achieve your goal and leave. What I'd do again: stay in the lakes (Maggiore/Como) area and do a day trip to Milan via train. Keep the bread crumbs from breakfast to feel the birds on Duomo square - it will save you from annoying 'salesmen' who try to sell you corn for 3-5 euro and you'll still get your iconic birds pic in front of Duomo.