Have done a similar trip. My top tips:
1) Wear your bulkiest items on the plane, if you can--sweater, jacket, scarf, jeans, heavier shoes. Pack the light stuff.
2) Roll up everything very tightly. I love packing cubes from eBags. Or just cramming stuff into every nook and cranny (socks tucked into shoes, etc.).
3) Pack as few shoes as possible. Maybe wear your walking shoes and pack your dressier shoes or sandals.
4) Think in terms of a color palette of things that you can wear with anything else you pack. I like to stick with navy and brown, and a few things with colors. A scarf that matches everything can work great for rainy or colder days, to keep warm, to jazz up a one-color outfit, etc.
5) Cross-body bag for your daily purse/tote. I use a LeSportSac or similar bag that can hold most of my entertainment items (phone charger, a book or tablet, medications, makeup and other liquids for airport, etc.) and then use it for my purse when at the destination. I like cross-body because you can keep your hands free, and keep the purse in front of you in areas that may attract thieves, etc. You can also rest your arm on it. Something like this:
https://www.amazon.com/dp/B002A7WG3A/ref=twister_B001GNBJ8M?_encoding=UTF8&th=1