We started bringing DS's buddy along on trips when they were 11/12, so close to the same age as your DS. We're big fans of Wyndham Bonnet Creek, and we get a 2 bedroom unit. I would recommend a two bedroom if you can do it, lots of options off-site.
As for tips with someone else's kid, here's some thoughts in random order:
- carry a signed letter stating that you can obtain medical treatment if needed along with a copy of insurance card
- lay down some ground rules for keeping their room and bathroom clean - we did daily inspections last year and that worked better than the first year where we just told them to keep it clean (my guys are scout buddies, so this seems to resonate better with them)
- we allow them to split up from us...just a little bit that first year, like they could go on one ride while we went on another or at the resort they could go play mini golf or ping pong without us. We explained that they could earn more and more independence as they proved that they could be mature about it. You don't have to have it all figured out up front, you can go by feel as the week goes on.
- if you can, take a short weekend trip close to home first (If you haven't already). We take this friend along camping pretty frequently, so we pretty much knew what the chemistry would be like.
- speaking of chemistry, expect that they'll chip at each other a time or two over the course of the trip, that's when a bigger condo space helps - they can each go to their own corners to cool down for a bit.
- our guys like to know what the game plan is - I print out our agenda and put it on the fridge in the unit, and then each day I jot down the Fastpasses and ADRs that we have, one for everybody's pocket.
- gift cards - great for managing spending money and snack money. REGISTER THEM, for that inevitable moment when someone loses theirs. You just hop online and transfer the value, crisis evaded!
- has the friend traveled much before? You kind of take for granted wheat your own kid knows about traveling, you may need to explain things if DS's friend hasn't traveled much. That first year DS's friend didn't bring anything to do on the flight, just something that I take for granted that DS brings along something to keep himself occupied. He was fine, of course, but just one of those things.
- is the friend a Disney kid? DS's friend had been only once before our first trip - so interesting to see it new through his eyes! But it did require patience from all of us. Like we'd be in the middle of AK and he'd say "can we go on that one ride where we flew in the air again?" DS has been going since he was 10 months old, so he was less than compassionate "you mean Soarin' - duh, that's in Epcot!" So prepping your DS's mindset might be nice if his bud hasn't been living and breathing Disney since he was young.
- I text a few pics every day to DS's friend's dad, I know it was comforting that first year especially (he's a single dad and can be a big mush sometimes, very sweet)
- our guys have cell phones, we all have one another's numbers saved. We bought a Fuel Rod external charger for each of us, they can be swapped for full ones at a few places in each park. We love these for peace of mind when we split up, nobody has an excuse for not having a charged phone. We also set a backup time and place to meet up in case technology fails us.
We really enjoy bringing a friend along. My DS is an only child, so having a friend along is really nice for him to have someone his own age to pal around with (although DH still gets pestered to throw a ball around the pool with them sometimes!) Oh, and I feel like they're more likely to buddy up with other kids around the resort when they are together vs. when DS is solo. I'm sure you'll have fun!
