Actually I was thinking about customs on the return, when reentering the US in Miami, which can be a nightmare.So it doesn't really cut into your time in Jamaica, just lengthens the trip home. I still vote for P.R. as the easiest trip for a short hop.

Yeah, I was thinking about the customs return back in the US. Cancun airport was not even half as bad as Philly with its "computer slowdown". And when we returned from France in March, the customs guy at Philly decided to unpack *every* single item in our suitcase. He even opened vacuum sealed packages of jams and smelled them (and no, we could not give them out as gifts since they were now opened).

A quick trip is a real treat. I do think a nonstop flight is easier and allows you more time. The easiest thing is to look at every nonstop from your nearest airport(s). By the way, Philly has expanded and the customs/immigration hall is now huge with lots of staff, I doubt it would be a problem anymore. I would avoid Miami like the plague.

I agree with Cartera45, I too was amazed at how short of a time it took to get through Jamaican customs... apparently it is the only thing not operating on "Jamaica time" on the island!

Return customs back into the US is also a breeze at Charlotte-Douglas Int, so short trips are no problem for me!

A three day trip is not unreasonable IMO if you can fly there in 4 hours our less. Where are you coming from?

As for destinations, take a look at weatherbase.com. As noted above, October is the height of the hurricane season, and it is also rainy in most of the Caribbean in October. I would choose another place which is not on the East Coast of the US or the Caribbean. A place like Acapulco would be warm, but could be rainy too (no hurricanes though. . .)

Agree with Cicerone that the rain/hurricane risk is not good in October in the Caribbean. If you want warm/hot weather, no rain and great golf, go to Arizona! Phoenix and Scottsdale are great that time of year, and a non-stop flight from EWR in 5 hours (but with the time difference you will arrive 2 hours later on your outbound which kinda makes up for the longish flights). Check on the Camelback Marriott, the Mountain Shadows Marriott and the Phoenician. All have spas for pampering, the one at Camelback is really world class. You should be able to find some deals, as school is back in session and it is too early for the snowbirds (December and later).

Santa Fe would be nice too.

You can also do Nappa Valley....if you are into wine. There are some wonderful intersting places to stay. Explore, get Spa'd, eat great food and divine wine. Very upscale, very romantic perfect for a long weekend.

For a quick trip out of Neward, I would definitely recommend Bermuda ... flight will be short and October weather will be beautiful ... perfect destination ... love those pink sand beaches!