A group of us New Englanders have been to Puerto Rico to climb and tourist twice in recent Februarys ( once just before the pandemic hit and this past Feb.) and enjoyed it very much. While it surely isn’t Kalymnos or Spain in terms of the concentration of quality climbing, there is surely enough good climbing, much of it very accessible for folks based in San Juan, to keep a team busy for an extended visit. There are several areas, mostly short but decent quality climbing, in the San Juan suburbs—-especially good for those climbing in the 9-11 range ( there are harder routes as well). The Ciales region, about an hours drive from S. J. has several developed crags with routes up to at least 12+, and an enormous amount of potential ( but for those danged private property issues!!!). Transplanted Coloradoan and now the principal developer in the region, Eli Helmuth—Flying Coconut Ranch—says that the next valley west is even more impressive. There are other good areas scattered around the island—most with beaches within easy reach ( and one even right above a beach). Definitely worth a visit and simple to get to from the US.
I’m sure you’ll hear about Cayman Brac—which definitely sounds worth a visit, though more complicated ( and expensive) to reach. I also hear that Columbia has quite a well-developed climbing scene. US climber Todd Swain has also recently published a guidebook to the climbing in Belieze, so that is another potential option, though not yet as well-developed as the areas mentioned above. Cuba is also another option with several well-developed areas ( particularly Vinales) , an English-language guidebook, and much potential, but I am not certain what the current access situation is there, as ( rarely enforced) climbing bans have occasionally been reported and I believe that it is still fairly complicated to be able to get there from the US.