I'd add to take twice as much of everything than he thinks he'll need - twice the imsulin, twice the test strips.
Also, choose an insurance company that covers pre-existing medical conditions.
I'd also take glucose tablets - both in hand luggage for immediate use, and in his suitcase to use while away. They're not always easy to get hold of abroad, and are compact to pack.
When he's on his lads' holiday, remind him that alcohol can mask the symptoms of hypos and cause delayed lows too. Stress that testing lots and paying attention to his diabetes while away with his friends will actually minimise the impact on him and his mates because that way things are less likely to,go,pear-shaped.
Make sure his friends all know what to do if he has a hypo and know,how to,contact the emergency services in Greece in the rare event they may be needed.
Perhaps also get him to,check in with you once a day? He may hate that idea but it would be reassuring for you.