I just finished putting together my luggage for my Italian trip. I try to keep things simple when I travel so I don't tend to lug around too many makeup or beauty items.
Regardless of the destination, I always bring sunscreen! Being both pale and having sunlight sensitive skin means that I need sunscreen whenever I'm planning to be outdoors for more than half an hour or so. I've been using this particular line for a while and it has a nice dry feel. I realize that I'm probably going slightly overboard with SPF 70.
The moisturizer I'm using at the moment is the Hadanomy collagen line from Sana. It has a really nice light and watery texture. For night time I have Body Shop's seaweed essence which I have been using for a really long time now. (I think this is my 7th bottle.) It's especially good for calming my skin after a day in the sun. For washing my face I'm going to bring along Shu Uemura's cleansing oil. This one is amazing at melting makeup and sunscreen for an easy rinse off, and leaves my skin feeling incredibly smooth and moisturized. And of course oil blotting sheets are never far from my side in any situation.
To save space, I buy little travel sized containers from Daiso to fill so everything barely takes up the space of a coin purse. I generally leave my hair up to the mercy of the hotel shampoo.
For travelling makeup, I prefer items that can fit in a small cylindrical pencil case. BB creams keeps everything simple and I can just apply with my fingers right after sunscreen. I really like this one by BRTC, in part because it has broad spectrum SPF 50. Despite looking dark in the tube, it matches my skin tone much better than foundations that look light but somehow ends up yellow or darker on my skin.
The pink lip gloss tube looking thing is actually a cream eyeshadow from Jill Stuart. Also for eyes: two gel pencil eyeliners in brown and black, and a brown eyebrow crayon. For lips: Dior's Lip Glow balm and a natural coral lipstick from Jill Stuart. I'm not planning on wearing mascara but I brought along a small sample tube of Dior. The perfume is a miniature bottle of Dior's J'adore. I chose it because it has the toughest lid to pry open out of all my miniatures, which I figured means it won't spill. (In case you haven't guessed, Dior and Jill Stuart are my favourite brands.)
I didn't take pictures but I also always take along a small "first aid/medicine" bag filled with Tylenol, band-aids, safety scissor, cough drops, vitamins, and single use eye drops and moist disinfecting towelettes.
Added bonus: accessories!
I always try to bring one each of clip, hair band, and scrunchie for flexibility. These ones seem to fit the Italian theme. (Marine and Venetian lace?) I'm generally not fond of wearing jewellery since I have to be constantly cognisant of them to prevent snagging on something, or when washing my hands. Just a simple (and cheap) bracelet and a cross (from my Gothic Lolita days) because "when in Rome...".
My friends are still convinced I'll spontaneously combust when I try to step over the threshold in the Vatican or turn into a bat/cat/black-pool-of-goo. I maintain that I've been in plenty of churches before and I haven't yet attempted immolating any clergymen.