We did 9 days, 8 nights last year (and will again this year) with just carryon.
- No kids, which does make it easier.
- I have a 22" rolling bag, and my wife has an 18" (though she'll be upsizing to 22" this year). Mine has a matching daypack that fastens on, so gives you an extra bag without having to have an extra bag. Just don't stuff it too full to fit into an overhead.
- We take extra shoes (last year I had mine + DW's in my larger bag - this year she's on her own!)
We usually plan on getting some of the clothes at the resort (last year I got a sweatshirt, which would have been bulky to take along).
- I pack enough underwear for the trip because it packs up better, and in case we don't get to laundry while we're there, it works out better. I can always buy an extra shirt.
- We always ship a box from the hotel the morning we leave, so we aren't as concerned about leaving extra room in our bags on the trip there.
- I bought one of the Scottevest/SeV vests yesterday - I hadn't heard about them until I went to the luggage store. I'll be trying it out in 9 days! It has 22 pockets, and the tag says "It's like a bonus carry-on" - you wear it to the airport, take it off to go through the scanner, put it back on. Any clothing with a pocket big enough for an iPad, and 21 left over is OK by me.
http://www.scottevest.com/v3_store/New_Travel_Vest.shtml (they make men's and women's versions).
- DW's personal item is her purse, which is a purse/backpack. Mine is a Rickshaw commuter bag
http://www.rickshawbags.com/bags/commuter-bag.html for the laptop plus everything else that doesn't fit in one of my 22 pockets.