Quote from retaildaytrader:
It would depend upon if you have a family or not and if your idea of a good time is spending it by yourself. An island is just that...an island with limited people and resources.
If you go to any 3rd world country like Jamaica then you expose yourself to the usual scam artists and drudgery of the third world. I would not pick anywhere in the Caribbean because once you get past the "all inclusive" resorts then you have to deal with the real world Caribbean which is not pleasant. Ever walked through downtown Montego Bay? You will find out what I mean once you have done so. Montego Bay is nice if you stay inside the resort, but take one foot out and the realities of the third world become apparent. I was happy to leave that place.
In the United States, San Francisco, New York City, and Washington DC are the ideal places because they are big cities with a lot of things to do, people to meet and you can have an actual life at the end of the day. I guess we could argue other locations as well like Austin. Austin has no state taxes, a booming economy and is a college town. It has an awesome nightlife and you will not get bored at night, but by day is a different story. Los Angeles isnt a bad place, but there is no way to get around without a car. You can get around without a car in SF, NYC and DC easily as long as you know the trains and right buses to take. Los Angeles also seems less people oriented. Florida is cool, but it doesnt seem to be either culturally or career oriented. Its like a cool place but without a purpose or reason. I hated Seattle because it rained all the time and didnt seem to have a nightlife. Portland was nice if you like to relax and it wasnt hard finding the ladies.
Pattaya City in Thailand is a beach-community with lots of things to do. If you are a single guy, there is no issue in hooking up in Thailand or having fun. Lots of places to rent on the cheap. Cancun is a lot of fun, but again, once you get past the resorts then all you have left is Mexico.
I think you will find that once you get beyond the vacation-oriented activities of the various islands and other such spots that there is nothing more to do. You should just stick with the large well known cities in America like New York and San Francisco.
Hong Kong was mentioned earlier in this thread. I like Hong Kong, but there is a great amount of pollution all over China. It looks like the worst days in Los Angeles when the smog was really out of control. Its a nice city and you should go there at least once in your life.