Getting there is quick and easy
Half the reason most people don't book trips is the long-ass flight there, which is why I have yet to go to Thailand. Puerto Rico feels like, and is, a pretty serious escape … and yet it's less than four hours direct from New York, Boston, or Atlanta, and less than five from Chicago, Dallas, or Houston. And you don’t need your passport, which means -- yep -- no customs. That shaves a couple hours off the travel time right there (maybe three if you're the sort who always insists on bringing fruit on your flight).
Driving there is a cinch
I was most pleasantly surprised about this fact. When I went to Costa Rica -- which, side note, is likewise incredible -- I severely overestimated the simplicity of road travel; my logic being "yeah, that's probably only, like, two hours away." It wasn't. As a result, a lot of time was spent in transit on many a teeny-tiny dirt road. Puerto Rico is similarly divided in the way that there is a "dry" side and a "wet" side (aka beaches vs. rainforests). But thanks to major highways and not as much land to cover, you can actually hit both sides in a day.