Now that the Summer vacation season is over, we are starting to see some great travel deals. Here is one from JetBlue: Book a 4+ night vacation in Puerto Rico and get $100 off. Book a 4+ night vacation in the Bahamas and get $200 off! Check out this page of JetBlue Coupon Codes to get access to these deals.
I've never been to the Bahamas or Puerto Rico, but I did visit the Virgin Islands as a kid and I have fond memories of that island paradise, I'd like to go back. It's like spending a week of your life in a Beach Boys song.
This really is the best time of year to travel to the Caribbean islands. Although the Summer season is over, there is still very warm weather in October (it's 88 degrees in Nassau today) and you really get the royal treatment when you travel just after the tourist rush. You'll find that prices of things are much cheaper and places are just less crowded. Everyone wants to travel to the islands during the Summer when kids are off school, so going just after school starts will let you take advantage of the hot island weather without all the crowds and kids around.