why not go for somewhere exotic like Bali? It has everything you have asked for including AI, although I would strongly advise against this as eating out is very, very cheap and food is lovely. Stay away from Kuta and pick somewhere like Sanur. Try to have a few nights in Ubud as well. Check the Far East forum for more info.

Here is where I recommend:-
http://www.bermudatourism.com/index.aspx

Thanks for the help, any more ideas?

How about this one?
http://www.gillscruise.com/showcruise?cruiseid=16957

I think cruising is the ideal vacation- you get to see lots of different resorts, but only unpack once,- apart from drinks it is all inclusive.- Many forms of entertainment on board, free. You can be as social and as active as you wish, as there is lots to do and lots of tours to take at the resorts, or you can stay secluded and do your own thing at the beaches etc. Takes a lot of the worry and stress out of vacation planning. It is great value for money also...
Plus the couple of days in NYC at the end will be a great change of pace. Lots of wonderful sights to see..