In briefcase/laptop bag:
government issued ID (driver’s license if necessary)
all confirmations for hotel, restaurant reservations, car rentals and flights.
list of restaurants and sights
map, if I have one
laptop/charger
Cell phone/charger
Canon G11 point & shoot camera with case, battery and memory card (optional)
Kindle, book or magazines
cosmetics (2-3oz Nalgene bottles in 1 quart ziplock)
pills in a small Mon-Sun organizer
makeup
1-2 granola bars
shawl
wallet
sunglasses
business cards and paperwork for meetings
pens
In roll-aboard:
small black handbag
brush or comb and non-liquid items like deodorant, toothbrush, razor
1 suit with 2 matching tops
1 dress
1 skirt with 2 matching sweater sets
1 pr black jeans
2 nice t-shirts
1 casual skirt
bathing suit/cover up (optional)*
1 pr dressy black mid-heeled sandals that can go day to night
flat black nice sandals
flip flops and hat (optional)*
underwear
workout clothing (optional)
hose and knee high hose (based on destination)
umbrella
Eagle Creek cube with first aid kit, extra TSA lock, alarm clock, Tylenol, Tylenol PM, blister protection, rolling tote bag and other assorted necessary items
On plane: wore ballet flats, jeans, tshirt, fleece
This is a list prepared for a 5 day/4 night trip to San Diego in warm weather where I was seeing clients who would notice if an outfit was repeated. Add a coat/scarf/gloves/heavier shoes if necessary. *After San Diego, I spent 4 nights at a beach resort in Mexico – and fit everything in a carry on and tote bag.