Assuming he's going via the Birthright Israel program (I believe Jace mentioned he was, somewhere on Twitter or something), he's probably never going to
see Gaza, much less set foot in Gaza. It's a very secure, very heavily supervised trip. From the wiki article (emphasis mine):
Security measures
Security policies in place during the trip "ensure a comprehensive safety umbrella":
- No travel to the West Bank, Gaza, or East Jerusalem other than the Jewish quarter of the old City
- Participants in each group remain together at all times and follow a set schedule of activities
- Participants do not leave the groups to travel, explore or visit with Israelis on their own during the ten-day trip
- Public transportation is not allowed at any time
- At least one highly trained, armed escort accompanies each group throughout the entire trip
Besides, even if he isn't going via that program, if tries to get to Gaza he won't make it. I'm not saying he's going to get shot at the border, I'm saying that, again, the security measures there are going to be more stringent that we could possibly fathom, and that's even discounting the ongoing invasion. He probably wouldn't even make it to the border.