Travel Shoe/Clothing Help Needed

[PorterInjax]

I have a trip planned with my fiancee' to Italy towards the end of June. We are going to spend a few days in Rome, then off to Florence, next Sorrento for a bit and then back to Rome.
I have been a "professional traveler" for over 20 years and abide by nothing more than carry on rule. The trip is for two weeks.
Most of my travel has been for business over the years and packing for international trips while on biz has been relatively easy. This is purely a vacation trip and I'm already struggling with what to pack.
I'm not worried about whether or not I look like a tourist but I do want to be a bit stylish while in Rome and Florence (been to Rome on biz a couple of times). I've never been to Sorrento which we are using as a base to explore other areas. Going to rent scooters for a bit also. What the hell do I pack to be covered and still do carry on?
The easy thing would be to pack a **** load but I don't want to do that. I certainly don't mind having clothes cleaned either.
Shoes? Clothing? Thanks

 

[Nicola]

With that schedule you'll be spending almost all your time on trains,planes or automobiles.

If you really want to hit all three areas consider an open jaw flight.


June? Lightweight jeans will cover almost all your needs. Pack a pair of linen pants. Maybe one with a light colour . Wear a light weight summer blazer on the plane. Some thing that you can wear with the jeans or other pants. Add some light weight shirts.

Basically your done. If you go some place that requires covered shoulders you'll have the jacket.

 

[PorterInjax]

Thanks. This is the first trip since my back packing journey after college graduation that is 100% vacation that also includes so many stops.
Obviously, from my post, I've been struggling with this but plan on wearing a linen blazer or sport coat on the plane. Couple of pair of linen/cotton trousers and yes, shorts. I don't want to pack more than two pair of shoes. These would be in addition to what I wear on the plane. I think it's the shoes that I struggle with the most.

 

[spectre]

Desert boots like Clarks are great. Look good with anything but a suit and are very lightweight.
Wear a dark brown pair on the plane and pack a bone pair for light coloured slacks. Add well-made flip-flops for your shorts and you won't be overweight.
Lands End has swimwear which also double as shorts.
Maybe wear one pair of cotton pants, pack a second plus shorts. One sweater for night, couple of shirts, couple of polos and couple of tees.