Hi Jmeilike, welcome to Cruise-Chat! Congratulations on your up-coming cruise! We've sailed many times in October, and are going again this year (my hubby's birthday). So far, we've been VERY lucky with weather. The southern is my favorite, in fact, I try to book it as often as possible. We've even gone down to Trinidad on one itinerary and Tobago on another. Grenada is another one of my favorite ports as well as Dominica and Barbados. We had one that went to St. Vincent, it reminded me of what the Caribbean ports used to be like. The steel pans with dancers greeted us at the pier, they had rum punch awaiting us inside the small shopping area, and the locals were so very friendly (not pushy).
Please let us know which ship you select! Best wishes!