My two cents, don't plan a trip to spend a week on a boat with anyone you have not spent a week (give or take) with before. Just returned from a trip with two other couples, both of which we spent a week with on land. Trip couldn't have been better, we all knew what we were getting. We booked a four cabin sailing cat with the thought of adding a fourth couple. In the end, we opted to just keep it three couples as we ALL had not spent any significant time with one other couple. Your trip appears a bit different, unless your son likes hanging out with old people (and yes, all parents are old people-from a child's perspective). You need to find a couple you could spend a week with AND has a child your son LIKES. Funny thing, when we were finishing the check out on the boat, the navs had an issue that couldn't be repaired that day, so we agreed to move to another boat-a three cabin version of the same. If we had the fourth couple, we might have had to wait for our boat to be repaired. Things just have a way of working out...
As far as your four questions, refer back to my two cents above, you should know what you're getting. But here are my thoughts:
Eat out or cook? Sure, we ate out. But each couple cooked a meal one night (maybe two nights in your case) and we team cooked what was left on the last night. Cooking is part of the fun. BOTH!
Sail or sit on a beach? If they don't want to sail and prefer to just sit on a beach, book the mono and tell them to meet you there-in a Jeep. We sailed to get to the next bay, beach, bar. BOTH!
Neat or not? Nothing could be worse than having a slob on a boat, unless you're a slob as well, then I guess it wouldn't matter. In our case, slobs may have ended up overboard or forgotten. My advice, NEAT!
Breakfast Beer Yay or Nay? Drink 'em if you got 'em. or don't. But if you'd get a funny look if you had a beer with your bacon, pick another couple. BOTH!
As far as missing criteria, I'll defer to others. This was only our second trip, first was with our two kids last May. Upon return, I had a goal to do it with some friends-that I KNEW I could spend a week with...
EckyEcky
