Great seats to a single sporting event, concert, show, etc.
A pair of season tickets to a local team, skiing, theater, etc.
If interested, that is enough for a nice new Driver or potentially an iron set if the guy is a golfer.
Round trip plane tickets for 2 to a domestic destination.
Electric bikes are popular now and some are in the $1000 range.
Scheduling a fitting for a reasonably nice suit (not Wall Street nice, but a lot nicer than Macy's).