You are right multi purpose trips are difficult. I am going on a 3 day multi trip , but not as extensive as yours. I need one business outfit, a more business casual outfit, two days of some sightseeing and a bit of shopping, and one formal evening event. also need my exercise gear for morning at the gym, and an outdoor run/walk.
First off I am narrowing down the shoes..will wear my loafers on the plane, and for the business casual event, the same cotton ankle pants and white denim jacket. Then need for the business a pair of dressier pants and my navy blazer, navy pumps, dressier t, and have a sequin black and white top with a floor length silk crepe skirt and higher heel black sandals. rest of the clothes will be extra t's jeans, and my navy print bomber jacket. My new black and white sneekers will have to do for the gym and with the jeans for the other daytime activities. For the gym I have track pants that can also be worn the new "sporty Luxe way with any of the t's and jackets.for other daytime activities. I will also throw in a cardi and if I have room I toss in extra t's as they do not wrinkle if rolled and take up little room.
You seem to be taking a lot. maybe others will have some good ideas on editing-especially taking so many shoes, as they are heavy and take up too much suitcase room. I love road trips as you can toss a lot more in the car.