Besides San Juan, if you get a chance, you must see Megan's Bay from a hilltop on St John's in the US VI. It will remind you of the most beautiful postcard you have ever seen and you will remember it for the rest of your life. I think one of the Rockerfeller's owned property nearby.
And, if you sail at all around the islands, I mean really go sailing, now that is enough to stir your blood. Sailing by moonlight, if chance permits, refreshed by the salt air are never-to-be-forgotten memories.
Don't let the company be a barrier to a great trip. Make it what you want and do not sweat the small stuff.
Marcus sounds like as good a prospect as any you might find. Just start an email dialog and see where it goes.