We went on a four day with my then 13 year old boy and our 16 year old girl. On our trip there were more children in the 13-15 year old group which is ideal for your 14 year old. My daughter who was a high school junior at the time met a few people her age, but I think it depends on your cruise. Tell him to check out common grounds, the club for teens, as well as the 14 year old. You really can't tell till you get on the cruise and check it out. there is so much to do, I am sure he'll have a ball!