We had the experience of bringing a newbie friend on our last trip. I'm not a great tour guide either and I had a little bit of anxiety about it. Like if something went wrong and he didn't have a good time... it would be all my fault.

We did a lot of things together in the beginning but our friend really got into his own groove after a few days. He enjoyed exploring on his own and meeting new people. It was fun hearing his impressions of things and seeing Jamaica from a different perspective. We experienced things that otherwise we might not have. We stayed at the same hotel but eventually we moved off to two separate hotels. He hired a driver that took him around to experience other parts of Jamaica... .while Markus and I just spent the last days relaxing on the cliffs. It worked out really well and we have so many great memories now from that trip.

I guess it really depends on your friend's personality. You mentioned there might be two friends coming along, so they can keep each other company on the days you just want to chill on the beach. I agree with Sandy-girl that a good driver can take your friends around to experience excursions and such.