You are NOT crazy!!
We're going to Europe for 5 weeks September through October, which means it will be hot when we get there and might be cooler at the end. I've already started on my capsule wardrobe just to make sure everything (still) fits and that the colors go together. Plus shoes.
If you don't like shorts then try capris. I would advise against skorts, unless you wear underwear and not use the panty option. I tend to wear my bottoms several times before washing and skorts can be iffy. Because we're going into many churches, I won't take any sleeveless shirts, just to keep it easy. I have three long sleeve "travel" shirts from EB that have roll-tab sleeves and drape nicely, 4 short sleeve button up shirts (2 from Orvis, 2 from Costco, all shirts fold compactly), and two t-shirts (one striped). I love my Athleta Brooklyn Ankle pants which can be dressed up or down-plus a lighter color pair of pull-on ankle pants form LLBean, and probably one pair of shorts. I'd like to take a skirt or dress but am having trouble with that one. Now to figure out the sweater/jacket option. I have a beautiful Pack-n-Go Jacket in spice from Orvis but it's water resistant, not water proof (maybe this doesn't matter?) and I have a couple of golf jackets to choose from that are lightweight and easy to pack.
I'm taking Keen Elle Backstrap sandal in Brindle/Birch, which are comfortable and cute, and am thinking about taking my Naturalizer Selah slip on tennie in turtle dove. They are leather/suede and are waterproof, but, heavy. Still thinking on this one.
To help overall packing, I create lists and add to them when I think of it. I'll have the wardrobe finalized by the middle of August. And all of this will fit in a carry-on plus one day backpack.
Hope you have a great time!