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Any suggestions somewhere warm to go in October

My fiance and I are trying to decide where we want to go for our honeymoon.  I feel like we are totally lost and just kind of wandering with the whole idea.  He has never been south anywhere (by that I mean the Caribbean).  I have only been to Cuba almost 8 years ago, with a girlfriend of mine but we went in Feb.  Also we were told we were booking a 4 star but in actuality it was only a 3.  I don't know where are good fun romantic places for couples to go.  We know we don't want a family resort and we do want all inclusive.  Any suggestions?
Also are we better to book through a travel agent or will we do better on pricing if we do it ourselves online?  We are trying to stay on a budget and from what I have seen so far I think we can do it for between 1600$-1900$. 
We just feel lost. Please help.
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