Weather in October
 

OK, bottom line, where should we go for the best weather for a 4 day/3 night jaunt? We want #1) sun and #2) nightlife. Puerto Rico? Bermuda? Aruba? Mexico?

Simply because of the time frame I would be safe and choose Aruba. It also depends where you flying from. Try for a direct flight as much as possible.

It's rainy in October. We were is Jamaica last October for 5 days and it rained three. We go every April and have never seen rain for more than a few minutes.

And I still say South Beach

Keep in mind the location of Aruba. It is about 70 miles from Venezuela. If you are only staying 4 days, you may spend most of your first and last day flying. It is worth it, but just something to consider.