The long-delayed honeymoon to Italy has arrived! Twelve days including traveling, ten nights: four nights in Rome, four nights in Florence, one night in Venice, and the last night TBD. I strive to be a light packer, especially in instances where I won't be seeing familiar faces. While I hate lugging and maneuvering suitcases, I'll be bringing a small wheeled carry-on, and either my Timbukt2 laptop messenger bag or my large dropped-shoulder Longchamp.

In addition to the usual suspects plus electronics (laptop, camera, Kindle, phone), I've packed the following:

Wearing on plane:
Cocoon winter coat (not down, good for the 0-10C range)
Cashmere travel wrap
Theory navy leather trousers
My Adea navy fitted 3/4 sleeve microfiber top
Ugg suede Chelseas

Packed:
Taos gold studded sneakers
Tieks black leather flats
Theory black leather pants
Kookai black leather knee-length A-line skirt
Everlane black collarless silk blouse
Equipment black collared silk blouse
My Adea black fitted 3/4 sleeve microfiber top
Equipment black flower print short-sleeve blouse
Wolford blush fitted 1/2 sleeve microfiber top

Gym shoes
Gym pants
Gym top
Gym bra
Merino wool zip-up

Questions:
a) Does this seem too much? I am planning on washing when necessary.
b) Will I need to check my Timbukt2 commuter bag at museums? It's smaller than my large Longchamp, but museums seem more accommodating of large "purses." The messenger bag is more functional for carrying electronics, and leaves my hands free, while the Longchamp is more stylish.

Other comments welcome.