We always put the wine in our carry-one, 1 bottle per passenger.
I include (like everyone else) all meds, camera, charges, phone, docs, basic cosmetics and jewelry. Basically anything that I need the first few hours and anything that can't be replaced on the ship.
If we are driving in to the port, I don't worry about packing a change of clothes, but if we are flying in there seems to be a larger chance of luggage being lost/delayed and I pack one change of clothing. I will sometimes, just pack a fresh shirt or a shawl or light sweater for dinner in case the luggage is not in the cabin before dinner. It usually is in our cabin before the life boat drill.
If the carryon is a little larger/heavier by all means use a rolling bag. If not, a nice shoulder bag or back pack is sufficient.
Been there - done that:
2005 Holiday, Sensation, Conquest,
2006 Conquest, Celebration, Holiday,
2007 Freedom Grand Med, Holiday
2008 Fantasy & Sensation,
2009 Fantasy, Holiday & Dream Grand Med
2010 Fantasy and B2B Elation
2011 Monarch of the Seas
2012 Booked - Breeze from Barcelona 12 days