As a positive result of our meeting last week (thanks again for all the good thoughts sent our way- they worked), the school has decided that it is a good idea to move DS(5) into first. At first we thought to do this after the holidays in January, but the school thinks no need for waiting and wants to do it as soon as possible. We are meeting this week to work out the details of the actual transfer.
I and the school have absolutely no experience with how this is done. (It is for the first time ever, that they are doing this. Our school district is actually very much against grade skipping, but finally in DS's case they gave our school the autonomy to decide.)
I am looking for ideas when and how to implement the skip. What are your experiences? Looking back would you do or ask for anything different?
The first grade classroom is almost across the K classroom, in the same hallway. DS has many friends (is quite popular) in his K classroom, so we need to explain it to the children why he is moving to first (they will see each other all the time, not so big school). And to introduce him in the new classroom in a good way, that does not prejudge him in any way.
I am also excited that there are other gifted children in this particular first grade, so DS will have some children that will challenge him in a positive way (he gets fueled by a good competition). On top of his base grade acceleration there will be some additional subject acceleration for math and science into 3rd grade.
I would very much appreciate any ideas, as this is approaching fast, and we really don't know how to implement it. Thanks.

When Ds was in first grade, there was a little girl that skipped out of his class into 2nd grade. She started with an afternoon. The kids all said good-bye to her as she picke up her things and walked to the accepting class. The teacher explained that her mom had asked if she was ready for 2nd grade and that she was going to 2nd grade to try it out and see if she liked it.
The little girl came back to first grade the next day and shared her experience with the class and the teacher told them the found that she was ready for 2nd grade. The kids said good-bye and that was it. My son came home excited and happy when he told her about it. Seemed to be a positive experience for all.

I don't know what the accepting class was told.

Knowing our school, the child just picked up with the schoolwork where she was, and was graded on what she did. I know there was some testing to find which group level she should go into in second. I'm not sure if that was done by the 1st or 2nd grade teacher.

DS6 (now in 3rd) did a mid-year skip from K to 1st. Since his K was half-day, we began the transition by having him go to K in the morning, eat lunch with me, and then go to 1st in the afternoon for the first week. The second week, he still did K in the morning, but then ate lunch with his new class. All went smoothly and he was fully transitioned to 1st after 3 weeks.

The kids were told that the principal decided to move DS to a different class. It's a large school, and there is a high turnover anyway, so that did not seem strange. We de-emphasized the change in grade level, and made sure to place the authority for the decision with the principal so that it would not seem that this was simply done at parental request.

DS just began doing the 1st grade work with his new class. There was no catching up. Since they don't allow skips unless the child is two grade levels ahead, that was not a problem.

He is still able to play with the kids he knew in K at recess, and is in the same cub scout den with some of those boys. So he still has contact with them.

Thanks for your input.
I have to agree, that when I imagined that one day he goes to K and the next day into 1st, it just did not seem right. I would prefer slower transition, and you gave me some great ideas. I am not worried about the academics (as he is still well ahead even of the first grade), or misbehaving. My main focus in this is the emotional part. DS likes things to be consistent, fair and predictable. Although, I think once he will see that the 1st grade is just more grown up in the whole learning approach he will appreciate it.

Hi Niki! Best wishes with the move. I think it will be "complication free" given the grades involved. I'm trying to remember some unexpected surprises that we encountered, but our midyear moves were in higher grades. There will be "little" things that sneak up on you, but most will be minor and easily surmountable. I have a cheesy example, but I'm thinking about "specials" etc. DS moved from 3rd to 4th, and while both grades did a similar art project that year, his ceramic fish is hanging unglazed because of the timing of the move, . (VERY minor, !) I think there were other little details revolving around specials, that we didn't consider beforehand. Much of it was art...moving his stuff from one class to another. (The art teacher worked with the entire school, and had the work grouped by classroom.)

With this same 3rd to 4th move, DS had a "going away party" in 3rd grade. While out for something, unbeknownst to DS, the class wrote going away letters (obviously this won't work in K!). They were so sweet, and the class presented them to DS with a rootbeer float party. This is not something I would have requested, but it was a nice gesture on behalf of the 3rd grade teacher that gave the other kids closure. The 4th grade class was also told about DS joining them before the actual move.

You might want to have him or you (or both) talk about the standard classroom procedures. For example, DS got "dinged" on his first spelling test, because no one told him it had to be in cursive. There might be some weird circle time rules/expectations that your son is not aware of. He'll feel more comfortable being aware of any such policies (who leads the line, how specials rotate, etc).

A few weeks into our move, we noticed that DS's AR sheets were still reflecting the old grade. So "technology" apparently wasn't aware of the move. There might be some electronic updates that need to be made. Just keep your eyes open and let the right staff know what's up. Remember, this is not their status quo and they'll probably need that extra set of eyes!

For my DS, they did it right before the first 9 weeks was over... his K teacher actually had a "party" for him, as a congrats. The kids in his K class understood what was going on... I'm not exactly sure how, but she explained it. But the kids also knew he could read at an entirely different level than they could, etc...

DS went to K on a Friday in the morning, and then in the afternoon he went to his new 1st grade class. On the following Monday, he reported straight to the first grade class.

Your DS sounds similar to mind, as far as being the "popular" K student. What I love is that DS has two boys from K that wait for him near the 1st grade hall in the mornings for breakfast - he gets to eat with whomever he wants. And he's transitioned into the 1st socially quite well...

Anyway, my point is that I do not know what to tell you to tell the students, or what to say to the school, but sometimes the simple "because" is all you need.

Good luck & congrats!

Oh, DS didn't want to skip due to missing his teacher. We were actually able to explain to him that sometimes in life, you have to make really hard decisions, but in the end, they are the right decisions. This was a big thing for him, as he is a perfectionist, AND really gets frustrated over challenges when he can't "conqur" them right away which can in turn teach him to choose the "easy" road when making difficult decisions.

He also tends to attach himself emotionally to adults in his life. But we told him that it does not mean he would never see his teacher again. So he came up with a plan as to how he would still see her (he says good morning to her every morning before class starts).

Maybe you can work with your DS to come up with a "plan" on how to deal with the things that he will miss most or to ask him how he feels about it all and address each feeling by coming up with ideas on how to make it "easier".

These are some great ideas.
I think I will try to work with the school on a gradual plan or at least leave it semi-opened to see how the first visit into first will go. I think after my DS will see that there are children just like him and everything has similar format, he will fit right in without any troubles. I like the idea of the goodbye party, which would substitute DS's birthday party in K. If the K teacher would be willing to let DS to come back from 1st to tell other kids how it is, and it ways it is different and it what ways it is the same, that would be great also. I am thinking (but it will me more on DS to decide) that he will implement similar plan to greed the K teacher in the morning (it is on the way to first anyway).
The great thing is that the gifted teacher has pulled out DS for gifted enrichment with the first graders from his future first grade. So they already know each other.
I will keep my eyes open on art and other specials. In last two weeks it seems that DS is all over the school being pulled out with higher grades, that his base K is really just a base for lunch, recess and center time (where he has his own projects anyway, but is in the same classroom). So I am hoping that the process will be easier than it seemed two weeks ago. I am just flabbergasted how easily is DS working on math along side 3rd graders, and so forth. I think he is understanding the school now more, and becoming more flexible.
We are meeting with the school this afternoon, and I am so thankful for all these replies, which gave me ideas how to approach this whole skip. Thank you all.
I will post update how it is going.

DS is starting the transitioning next week.
On Monday he will meet just the first grade teacher (when kids are in specials), so she can show him around the classroom and explain how they do things. On Tuesday he will spend some more time in First, and afternoon we will do a goodbye party in the K. DS will spend more time in First on Wednesday, Thursday almost full day and Friday he will go with the first grade on a field trip. The following week he should be full time transitioned in first.
I think this should work.
Thank you all for helping me with this.

Great! Good luck to you and him!!!