How about a charter or guided trip? If he has all (most) of the new gizmos, then it'll be hard to find something he doesn't already have.
But I'll bet he will definitely enjoy being out on new water (or familiar water) with someone who really knows their stuff, works hard to put him on fish, and makes it an enjoyable trip no matter what.
I've hired guides probably 10 times now, and have always enjoyed it, esp. when it was somewhere new where I wouldn't have any idea how to start (e.g., saltwater flats).
Mike