jr/shotglass said:
Get yourself one of the hotels at the far end of Duval Street, down by the southernmost point. Take the walk up Duval Street when you're ready to start your day, or after lounging at the pool for a little while.
If you're directing him down thataway, I've got to recommend the Southernmost Hotel. Best rates on the island (which still means you're paying $200 a night on a good night), plus free parking. It is a ways from Old Town, though, so if you've gotten a decent rate at the hotel the conference is at you might be better off there.
http://www.southernmostresorts.com/southernmost-hotel/
The Southernmost Hotel is on the quiet end of Duval Street, a block from the Southernmost marker. Roll out of bed and you're on your way. You will have to hike to get to the good stuff at the other end of Duval (it's a mile or two from one end to the other), but most of the fun is people watching anyway.
If you want to chill out for a bit, there's a pool with a tiki bar.