Is this first time to this part of Italy?

Capri will be very busy with day trippers. It's beautiful but very crowded and you are bound by ferry schedule unless you have a boat to yourselves which would be much nicer. In April tbe last ferrry was 6pm or so but maybe they are later in summer. There can be a long wait to see the blue grotto. There is a small minibus from the ferry station that gets you close to the entrance if you don't want to wait in the water. Is there something special your son wants to do on his birtday in Capri? The cabs are old cars and its a fun ride through town in them.

Ravello is beautiful. We had sandals made for us in 10 minutes on the square. Not as exciting for guys I would think but you pick out style color etc and have something unique. Capri also has a lot of the same type of custom shops maybe belts for men and the like. Don't miss villa cimbrone and the terrace of infinity.

I already mentioned Pompeii. Really unbelievable. Have a guidebook that gives you a walking tour to follow so you know what you are looking at and have the right orientation of the city. You won't be able to cover all of it anyway. Herculaneum is definitely worth it. Smaller more preserved and it's right up against the new town and easy inand out. Parking for Pompeii is all along the main road. It wasnt cheap but part of the vacation spend Bring cash and don't park anyplace you need to leave a key

We didn't have time for hiking vesuvius but would have like to.

We were catching a train from Naples so we took the local train from Sorrento earlier in the day and stored our luggage in Naples and did our exploring on foot. . It's an interesting place and the Archaelogical Museum was really interesting after being at Pompeii but it may be the opposite direction from where you departing. A walk down the narrow streets of Spaccanapoli is also interesting. We were there on day of a big soccer match and there was lots of activity and spirit and you got a taste of local flavor.

Distances are deceiving here. The roads as mentioned before are 2 lane and winding so everything will take longer to get from town to town for exploring and ferries day tours etc their schedules will greatly impact your visit to each place.

Do you like history or ruins. We didn't have time for Pasteum which probably has less visitors than Pompeii.