1. Trousers, I would think. I can't remember anything else being worn in the evenings but not sure I'd notice.
2. Usual mix of glasses if you mean the drinking kind. Standard wine glasses, beer tankards and shot glasses, both in the restaurant/bar and on the terrace.
3. Baileys and many other familiar brands are indeed served at the bar, together with other labels unknown to me but well worth a try. The House red and white wines are available from help-yourself pumps scattered around the hotel in the restaurant and other bars. There is also a wine list for which an additional charge may be made.
Have fun and don't forget the Greek Dancing lessons from the Animation Team. Yes, I was bullied into them by my wife. Made a change from the archery, shooting, theatre, cinema, water sports, body trim (??!) etc etc.