They are only a few miles apart, but jogging between them would be tricky. They are not connected by a beach (much of the shore between CTI and CSS is rock cliffs), so he would have to run on the road. That strech of road can be very busy and is not the safest place to jog.
Could he?? Yes. Should he, NO!!! I would advise against it. They tend to fly up and down the road, and there are many turns in it where he could be injured. No sidewalks, so he would be right on the road.
Thanks for the information. Paul ran on the roads last year in Jamaica with no problem - in fact, the drivers were far more courteous than those here in the US. If you've ever run on the roads here, you'll know just how dangerous it is
If you travel off the resort, unlike the US where we hop into a car to drive 200yds, you will see many people walking on the roadside. Drivers expect this and are prepared. Should you be reckless and run when it's dark? Absolutely not. But I definitely wouldn't say don't do it. Just remember to be careful, and keep your eyes, and ears, open.