I thought DD had a great transition. Our school has a bunch of transition events - first we have an ice cream social for new families and mentor families - gives kids a chance to meet some classmates, and parents to meet.
The first week of school, they have a two hour block where parents go in with the children to the classroom and give them a chance to explore, meet the teacher and classmates without any expectation that the parent is going to leave, no agenda either.
Then there is a one hour day on Wed where parents of new students come and they do the arrival routine, circle, etc but the parents don't leave and it only lasts an hour, then the next two day the kids go alone for two hours. Then the rest of the returning students join the classroom on Monday.
With DD, we just talked a lot about how she was going to go to a new school, Montessori school, after we went to the beach (we had a beach vacation planned in late august last year). She was somewhat excited, but after she saw the classroom she was REALLY excited. We had the delayed seperation anxiety. The first few weeks, she hopped out of the car (they have a car dropoff) happily and went in, then around week 3, she started having trouble and I had to walk her into the door and get the teacher to coax her in (since they are dropped off outside the atrium, which is a set of double doors from the classrom,s he couldnt see the fun the other kids were having, there wasn't a lot to entice her). I was just gentle, but firm that she had to go and she did just fine, that phase only lasted a few weeks and she was back to hopping right out of the car super excited.
So, hopefully your school has a good transition routine and I'd recommend going to all the events on that if you can.
