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I would have done it, there is a very good twos program where my son is currently enrolled. I also found a program with parent involvement.

What are you planning to do for preschool, start him in a 4s program, skipping 3s? Sorry I am not getting it, lol.

@SweetiePie: Ok, so basically, he'll be in a twos program this year, next year he would be in a 3s and the next kindergarten?

eta: I have a kid with a December birthday and the school year cut off is 12 31 but I held him back so he won't begin kinder until next year when he is 5 turning 6.

@SweetiePie: I would probably do it, I don't really see a downside. I send my son to a nature based preschool and it's ridiculously expensive for the hours that he's in attendance, but the experience is something I can't replicate, so for me, it's worth it. Not sure about the program you're considering, what is it that makes you excited about it?

I did two days a week for T in a similar program, 830-330 when he was 2.5. He loved it and it was great for both of us. I was staying home at the time, but was very pregnant and then had a newborn/baby. I didn't have the time or energy to provide him with the enrichment activities that his school did, and I still had 5 other days of the week with him. It was expensive but I felt it was worth it and he didn't miss a beat with preschool. I didn't have a sitter but maybe you could cut back on your sitter to one day a week?

We did one in Brooklyn. My son was 20 months when he began. It's been great but he was badly in need of socialization/separation. He is a really reserved kid, and I think it's given him a lot of confidence.

@SweetiePie: yeah it's very gentle! it took some kids the whole semester to separate!

I know it's very competitive in NYC, but are there any private preschools that offer wiggle room in terms of cutoffs for the twos class? DS misses the twos cutoff by the same amount basically (his bday is 9/3 and the cutoff is 7/31) but we asked and the preschool director said there is flexibility. In our case, we are in a nanny share and the other child (who he'll be attending preschool with) is two months older and makes the cutoff. We explained and they were fine with it. (Also, DS has hit his language explosion early so I'm not worried from a communication/understanding standpoint.) For reference, our program is 3 days a week, 3-4 hours/day, and we're in a medium-sized city in the south that is surprisingly competitive for preschools/daycare.

Our preschool (in NYC) has this type of program, for 18-24 month olds (when the school year begins). DS was lucky - there was space in the regular 2-3 year old class last year and they let him join that class even though he missed the cutoff by a month. They aren't that flexible anymore. We would have done the pre-preschool program though, and will with our next one if they miss the cutoff. His teachers in his current class (a mix of 2s and 3s - he is 3) often remark that all the students are very well-behaved and get a lot out of the class because they were all in school last year, either in preschool as 2 year olds or in the pre-preschool program. Our school sounds much like yours - very structured. The kids love it.

I'd do it. If its only 2 hour sessions, then I assume its in the morning he'd be home for lunch and nap. As he gets older and learns to talk more, you guys can go out for lunch together after school or go out for ice cream in the afternoons, so you will still have together time. Or you can just be hanging out at home together.

The other thing too is he's going to get sick. A lot. You might as well work on strengthening up his immune system now while you are at home and you have the nanny to help so that by the time he's in preschool full-time, he will get sick a lot less often. This is going to be a huge help by the time the next baby comes along. My friends who kept their kiddos at home until full-time preschool have been dying this year because of the nonstop illnesses (and the younger siblings catching all the bugs).

@SweetiePie: I figured that was the case, just didn't want to make any assumptions

We are also in NYC and DS has a fall birthday, so also missed the cut off for 2s programs. We ended up doing a half year of a "gentle separation" program that was really more a mommy & me preschool class, because I never left the room. It introduced him to the concept of class, teacher, circle time, snack time at a table, etc, which he hadn't had since I SAH, but I don't really think it was necessary. It wasn't at all academic, and was more arts/play focused. He went right from that into a 3s program, which I wanted, rather than doing a 2s program and being one of the oldest. I think it's really up to you--I don't think that he is any less "prepared" for preschool than the kids that did the 2s programs. The only thing is that I do think separation was harder/took longer because it was his first experience, but it was still only 2-3 tough weeks and now he's totally fine.

I'm not in NYC, but we are doing something similar for DD2 next year. She is a Nov baby, so misses the Sept 1/24months cut-off for the 2s class. They do a one-day/week 3-hr program for those kids, so we are signed up. Less for the academics & structure and more for the consistent social interaction with peers and other adults -- she does get other social interactions at the gym daycare and at Sunday school nursery, but it's not necessarily the same adults or kids when she goes.

However, having her in that program makes things easier on me, since it means I get one morning/week with no kids If I felt like it was somehow making things more difficult/too structured, I wouldn't worry about it and would just enroll her the following year!