San Juan, Puerto Rico

A rough around the edges neighborhood. San Juan has some nice areas - but crime rates are high as is poverty. Not the most vibrant urban life. But at least some gay life. And a beach in the city is a rare thing. Not glamorous, not overly safe, not convenient or easy - but hot PR dick.

In the late 1960s, it seemed every Eastern Airlines flight from JFK to San Juan was hijacked to Havana. It became a badge of honour. I think the Havana airport would be notified, the plane would land, the hijacker would be arrested, and the passengers would disembark and mill around before reboarding and continuing on to San Juan.

I know a boat you can get on! (Bye-bye!)

Why would anyone want to hijack a plane TO Cuba?

Way to hijack a post, actually looking to here from people who've been to San Juan. Focus please.

R1, yes I get that sense from Google maps. Literally looks like a Third World version of Miami. Interesting that there are literally no people walking the streets even in daylight.

Also I find Boricuans amongst the trashiest of Latinos, so that's not a determing factor.

Any alternative areas to look at? Landed on Santurce because a quick Google search showed it as the gay neighborhood.

Or should I just do Fort Lauderdale?

Everyone there will have moved here.

^True. The island is emptying out from a combination of high outmigration and a birthrate barely above 0.

R7 Interesting.

I've been to enough Latam countries to know the ones who flee are usually on the lower rungs of the social ladder. The ones who stay usually have opportunities and stay for the wealth & convenience (who wants to be an "immigrant" in the US?). Many are smoking hot.

Perhaps PR being a part of the US skews this dynamic.

You’ll do better on Vieques.

If you think of coming back to the mainland, consider St. Petersburg. Depending on your tolerance for heat/humidity or chilly weather, Consider November, December, April, or May which have far less snowbirds.

Why WFH in San Juan? Blah. Santurce is also massively different from block to block. Condado is worlds away from Loiza, much less anything south of Castro (Expreso).

I love visiting Puerto Rico, but even I would be a tad uncomfortable living there by myself.

Try the USVI if you want Carribbean US, or just stick to Florida or even NOLA.

R12 Trying to spice things up. Been to Hawaii about 100 times (SF here).

I do want some gay nightlife options as well, and sadly Hawaii has limited offerings. Also in summer (when I'm planning to go) its overrun by entitled families whose rugrats run free.

As does USVI (know someone who worked there for a bit and she couldn't get off the island any faster). She said it was boring and the natives mistrust mainlanders without shame.