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Packing for Croatia (23 days Sept-Oct)

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I always bring way too many clothes when I travel, but for an upcoming trip to Croatia (leaving Sept 21 for 23 days) I want to Pack Smart!
I need big time help!
My first dilemma was shoes. Rick Steve's books say bring one pair of shoes. Really? What kind of shoes would I bring for those times I wear a dress? And we want to do mild-moderate hiking as well, and I anticipate doing a lot of walking down cobblestoned streets or the like…. and if we do any water activities, I think I read somewhere where water shoes are recommended.
I am 5.4 and plan to bring mostly capri and long pants. When I wear shoes such as sneakers or something other than a a low-cut shoe (or flip flops), my legs look ridiculous - clunky…
So I bought some beautiful leather ballet shoes (Tiegs?) to try and they are really cute, but they're completely flat, and I think I need some kind of heel to do all day walking. My lower back got that old familiar ache after a day of walking in them to test them out.
I also bought a pair of Go Walkers. They seem like they'll be "ok", even though they are not low cut, they may be passable with dresses since they're a light color. I have a high instep, and shoes that come up too high sometimes really bother that bone on top of my foot. With the Go Walkers, I can "feel" the fabric there when I put them on so I'm not sure if they'll work out. (Maybe moleskin will help).
As for pants.. I've been hoping to find some really comfortable wash and wear (wash in the sink and they'll be dry in the morning) pants and capris that are no wrinkle, hopefully. I don't like really WIDE legs, but I don't want leggings either…. flat waistbands work best for me - no bulk at the waist, more flattering.
Are pants and capris what I should bring to Croatia for late Sept early Oct? No shorts, right? Would it be mostly capris? How many pair of each would you suggest?
I tried a pair of Lucy's Walkabout Capris in Small but the legs were a little wide, the pants a little too long and the rise (14 1/2 back rise, 9 1/2 front rise) was a little too short, surprisingly, so I think I will have to return them.
I never tuck my shirts in and I never wear shirts with collars, and my shirts I like on the little bit of the longer side, to cover my hips and fanny… Can anyone recommend a website where I might find cute shirts that are again, wash and air dry?
Any other suggestions for packing for this trip?
I understand that there are probably lodgings without elevators, so we should be able to handle our bags easily… and getting off and on busses and trains will be so much easier if we can limit the size and weights of our suitcases, and I really want to do it this time.
Another thing that seems to take up a lot of room and space in my bags are just the toiletries themselves! I have problem hair and use special shampoos conditioners and masques in addition to serums and stuff like that to try to quell the frizzes.. then theres the sun tan lotion, moisturizers (face and body), electric toothbrush, toothpaste, q tips, sleep mask, vitamins, ear plugs and sleep sound machine (my son brought a sound machine to Italy last year and though he used an electrical adapter, he said it smoked, and I'm not sure if it killed the machine, but now I'm wondering if mine will be safe? (and extension cords)…
Books to read. Hiking shoes?
Can someone help me? I know I need it. I envy those who can do it so simply. I have many clothes, so you'd think I could pull together a few outfits easily, however many aren't the kind I can wash by hand and that will dry overnight… they're heavier, and take up too much room in a suitcase… I feel like "travel clothes" are in order, and that I have to buy a few outfits.
I do know it's best to select a color scheme, say black and white or brown and white, and stick with it the whole trip and have everything coordinate with everything… the sweater for the dress should also be the sweater for the pants and top….
I find it all overwhelming.
Tips on suitcases and carry ons would be helpful too… backpacks even…
I'll take any help I can get because I'm not sure where to even start.
Thank you!

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