DH and I will be flying from NY to Dublin, spending a week in Ireland, flying to Greece for a day in Athens and a 5-day sail in the Greek Islands, then back to Ireland for another 5 days.
Definitely a first-world problem, but I am very restricted in what I can take to Greece. We have relatively low-cost seats and a tight connection in Geneva, so I can only take a small carry-on that weighs no more than 8 kg (about 17 pounds) and a very small handbag that isn't more than 4 inches wide (10 cm.). And all of this is further complicated by the difference of at least 20 degree F. in temperatures between our two destinations. Plus, the cruise is on a sailing ship, so we'll need both sporty for day and some smart dress for dinners.
Here's what I'm planning to take, including the heavier outfit** I will wear on the planes in both directions:
Bottoms
1 black skinny jeans**
2 pair black leggings -- one heavy; one lighter-weight with white stitching that also serves as pj bottom)
1 pair black shorts, along with a pair of very opaque Wolford tights that can be worn under them
1 cropped pant, lightweight
1 foulard printed dressy pant (purple/cream/black/loden)
Tops
7 Short sleeve tees (various colors, incl. white, loden, red) -- these also can serve as pj tops
1 long-sleeve lightweight tunic with pockets**
1 hi-low, ruffly bottom, ss pullover in lightweight black/wh/grey print
1 dress (tattoo print from Rodarte/target years ago) -folds very small
1 bathing suit
3 scarves (one large enough to serve as a pareo over swimsuit)
1 baseball cap (I get sunburned easily)
Toppers
1 black rain jacket**
1 thin zip-up black turtleneck sweater
1 tuxedo-style jacket (Isabel Marant)**
1 black shrug
Shoes
1 black leather Ecco sneakers
1 strappy black patent flats
1 cut-out black boots**
1 leather flip-flops

I can't believe that I've managed to squeeze this much into a small tote (which will have to be my purse while I'm in Greece) and a lightweight carry-on. The rest of what we're taking will stay in Ireland. But I feel insecure about this. And all the black in the Greek Isles. What am I forgetting? What is unnecessary?