what to pack when one large suitcase is what i bring for a long weekend

Visiting my boyfriend in Florida for a long weekend, I might bring enough clothes for a week and a half. The real challenge for this summer: packing everything into a backpack and a large travel purse. This is to be the test, and I hope I will be able to achieve it. I still haven’t figured out which pants I’m bringing, and which long sleeved shirts…but I’m almost there. My bag is nearly full, but it’s far from overstuffed.
I’ll be from Iceland to Greece, from May until September, so a variety of clothing is necessary. Layering will be of utmost importance, and I’m positive I will smell on several occasions. Deodorant and perfume will be very helpful.
My packing list follows…

So here’s what I’ll be lugging around for the next three and a half months:
Clothes
pajama outfit
2 short sleeved shirts
2 tank tops
scarf (decorative)
6 pairs of underwear
2 bras
2 running outfits—sports bras, tanks, shorts
4 pairs of socks
3 skirts
bathing suit
sweater/fleece?
1-2 pairs of pants
cardigan
long-sleeved shirt
flip flops
sandals (with straps around the ankle)
running sneakers
Toiletries
LL Bean toiletry bag
tweezers
nail file
nail clippers
deodorant
towel
razor/shaving gel
q-tips (only a few)
sunblock
shampoo
conditioner
face wash
body soap
lotion
moisturizer
hair bands
toothpaste & toothbrush
brush
comb
woolite
pantyliners
Makeup
(I normally wear none to a little bit)
mascara
1 eyeshadow
small tube of foundation
lipstick
lip balm (a must!)
perfume samples
1 pair fun earrings
nail polish
nail polish remover pads (3, travel-sized)
Medicine Kit
case to hold it in
Tylenol
iburpofin
anti-diarrhea
band-aids
tums
neosporin
moleskin
migraine medicine
cold/flu
benadryl
vitamins
rubbing alcohol
6 asthma inhalers & singulair
emergen-c (2-3)
drammamine
seabands
melatonin (to prevent jet lag)
Miscellaneous
mini-sewing kit (with white and black thread—in film canister)
clothesline
money pouch
journal
small package shout
earplugs
plastic garbage bags
Ziploc bags
universal sink stopper
power converter
ipod
stationary
phone cards
highlighter (1)
computer disks
gluestick/tape?
small naglene bottle (16 oz)
safety pins
pillow case
dryer sheets (to keep pack smelling fresh)
sunglasses
lonely planet europe on a shoestring
smaller wallet
twist ties
camera (digital) & memory
duct tape (around a pen)
daypack/purse
travel umbrella
knife or scissors
sharpees
photo of backpack (in case i lose it)
bandana
War & Peace by Tolstoy (I’ll rip out pages as I finish chapters; I’m a fast reader so I think this will keep me occupied until Spain)