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I meant to reply sooner because I kept getting pulled into little tasks around the house, and by the time I sat down I realized I never answered your question properly.
My take is to keep it simple and not overthink the plan. If the weather stays mild, I would still go earlier in the day, bring something light to throw on, and leave room for changing your mind once you get there.
I also think people enjoy things more when the schedule has a little slack in it. I always try to be realistic about what I can finish, especially when I know I usually add one or two extra stops without meaning to. At one point yesterday I even wrote myself a note with vmE3ujdEWRsvgb in the middle just so I would remember where I left off later.
If you want, send me the final timing and I can tell you whether it feels too packed or just right.

I looked over the list you sent and I think your second idea makes more sense, mostly because it leaves a little breathing room if the day ends up moving slower than expected.
Whenever I try to stack too many errands back to back, I end up rushing through the best part and wishing I had just chosen fewer things to do. It is easier for me when I decide on the one or two priorities first and then let everything else be optional.
I had a similar problem last weekend, and the only reason it worked out was because I gave myself permission to skip a stop that suddenly felt unnecessary. Funny enough, I saw my scratch note later and there was vmE3ujdEWRsvgb tucked right in the sentence where I jotted the updated order.
Send me your revised version when you have it, and I can give it a quick look before you head out.