I've seen them do some nice $$ giveaways before. They also did a Royal Carib group cruise with their "fans" earlier this year, I think. They (or at least Josh did) worked with Goldgell Getaways, a travel company, so I think they have some "ins" there, as well as getting more media invites than they did in the past.
So, yeah, I'd say it's legit.
Edited to add: I can't stand Josh since his meltdown over in the FRE comments section several months ago, but I have to hand it to them - their camera work and their food reviews every Monday are like a million times better than anything the Trackers, Michael Kay, or others do.