Hello DJ -
My name is Emily Roy and I work in the Program Coordination Department here at Go Ahead Tours. I've been a couple of our tours and have also traveled quite a bit independently. As someone who loves clothing, outfits, choices - I sympathize with your concerns about the one bag minimum! When planning a trip and packing my bags - here are some tips that I try to adhere to:
1. If you're not going to wear it more than two times, don't pack it! Every piece of clothing you bring should complement every other item or have at least two uses.
2. Stick with dark/neutral colors - (black, beige, navy) they look more European than bright colors.
3. Shoes – (admittedly the hardest part for me) – I usually pack one pair of walking/athletic shoes, an inexpensive flip flop, and a nice sandal that can pair with jeans or a dressier outfit.
4. Accessorize, accessorize, accessorize! Scarves/earrings/a neat piece of jewelry give your limited wardrobe just the color it needs. They dress up your outfit, are lightweight and easy to pack!
5. Buy fantastic items/accessories in Italy! The good news is - you can take two bags back on your return trip - I usually pack a collapsible duffel bag for souvenirs, shoes, clothing that I purchase abroad.
Additionally - here is helpful article from Fodors about packing light:
http://www.fodors.com/news/story_1901.html#
Let me know if you have any other questions!
E