How do two single hetero guys in their 50s decide on a resort or property to stay at where we will not feel as outcasts being single, but at the same time ... be amongst single adults (maybe 40s/50s) who are into having a good time/fun ... and also NOT be amongst a lot of "craziness" that is more commonly associated with younger singles?

Club Med Turks and caicos

In the most general way I think it has a lot more to do with which specific resort you choose, rather than which island.

Thank you. Any recommendations on specific resorts then ... for our specific scenario?

No sorry. I'm single and have traveled to Jamaica a few times but more often to Puerto Vallarta, Mexico. But I don't stay in resorts. I just find local hotels or apartments to rent. That suits me better.

But there are plenty of straight 40 & 50 year old guys who vacation in Cabo San Lucas (fishing is big there) on the Baja or PV... just judging from who I see out and about at the beach, in bars, etc. in those places.

Thank you very much, Suze. Really appreciate it!

The Caribbean place I've been most often and most recently is Negril Jamaica. Take a look at www.negrilonestop.com and see if that might appeal to you. It's 90 mins. outside Montego Bay (where you fly in). And shuttles are ~$30usd pp to get you from MoBay to Negril, where there's a dropdead gorgeous 7 mile beach and also places to stay up on "the Cliffs".