October is still right smack during hurricane season...though they'll tell you it's the tail end the hurricanes don't know that so they still keep comin'. Having said that, some years Jamaica gets one...or a few ...and some years they get none, no way to predict ahead of time just like no way to predict how much snow you'll have at home or how soon spring will come. We go every year in either October or November (a matter of a couple weeks difference) and out of 15 trips we've only had 2 with shall we say less than ideal weather. Neither trip was totally rained out but we had a couple days on both that were rainy and not full sun. This last year was probably the worst as they did have quite a few tropical storms as well as the hurricanes, temps seemed cooler though we weren't cold at all and actually it was nice to cool off in the evenings.
It's the reason the prices are cheaper that time of year. We'll keep going that time of year and wouldn't steer anyone away who wants to chance it. We recommend trip insurance for any trip of this expense and particularly this time of year. We always use a travel agent also so we have someone to contact should we need help getting flights changed to get home early if a storm blows up or any variety of other reasons too. Also, they can verify what you are covered for as there are various types of policies. I say book the trip!
We just went this past October it only rained once. It shows that it is the rainiest month and it is still in hurricane season but, you just never know. We took a gamble and it worked out great. We actually went snorkeling the day it rained. Your in the water anyway right! Have fun! I will say....we went the first week of December 2009 and it didn't rain but for 20 minutes. Maybe that's a possibility?
We have been to Jamaica 4 previous trips and they were all around the time of year you are thinking of going. For the most part that is a great time of year to go. The weather is beutiful and the prices are better. But! It is hurricane season . We never had a problem. (UNTIL LAST YEAR). I can tell you we were in only a tropical storm last year not a full blown hurricane. I am from Louisiana and I know only to well what they can do. This tropical storm was no fun at all. You have to make up your own mind if you want to take that chance. Like I said one out of four trips we got caught. GOOD LUCK.
October is THE RAINIEST month of the year. We experienced that first hand. The resort was flooded but we still managed to have a good time. We were in a tropical depression. But we now go every year but earlier in the year.
We always travel to the Caribbean in October. After all the prices are always cheaper due to hurricane season. Plus the resorts are usually only at half capacity. Jamaica has not taken a direct hit for a few decades. That is partly due to the mountains on the eastern part of the country. In fact you are much better off traveling to Jamaica instead of the Yucatan Peninsula (Cancun Area). That part of Mexico has taken many direct hits the last 20 years during that time frame.
We stayed at Sans Souci from October 3 till October 10th of last year. It rained 1 morning for about 2 hours on our second day. That was at 7AM. So it did not effect us 1 bit. They do say that it rains nearly daily up in the mountains, during that time of year. But we were not affected at all.
I will say that the week before we went, that the Negril side took a beating from a strong Tropical Storm. I believe CSA had some flooding issues in a few suites. Overall it is worth the risk in my opinion to travel during that time of year. Even if it is to the Gulf of Mexico in Florida
We were there Oct 22-29, 2010. It was perfect, resort was not crowded, sun all day long, with an occasional rain around 3 o'clock, which only lasted an hour tops. Soon as the rain was over, everyone was back on the beach like it never happened. It did rain one night and they canceled our beach dinner, but we ended up at the rockhouse restaurant and it was awesome. I would get trip insurance though just incase there is a hurricane or whatever. Wife and I still agree that when we go, we are going in October. Good Luck.