I see there are a lot of seasoned travelers on here so rather than stumbling through a million top 10 lists I put it to you experts. My best friend and I (both divorced, active 40+ males) are trying to decide on a vacation spot for mid-Oct. Will probably do a last minute thing but hope I can get some feedback around where to go. We are interested in beaches, bars and hold out hope that we may meet some female companions along the way to hang out with. Nightlife and great beaches are the priorities. I would also like to do a little surfing possibly. Not planning on breaking the bank if possible so have considered places like Jamaica, Dominican Repub, Puerto Rico, Cuba (I'm Canadian), or even Aruba. Any suggestions would be appreciated.