Stroller Advice - Leesburg,VA

We have a Joovy Caboose stroller that we got at a consignment shop so it is an older model. It has a place for the older child to stand on a platform or a "jump seat" -- the seat slides back and forth to allow the child to either sit on it backwards (ie facing the person pushing the stroller) or stand on the platform. The front seat on the one we have we now use as a regular stroller seat with a 5-point harness but it had an adapter for the front seat that accomodated our infant carseat. Once our daughter was finished in the infant seat we unsnapped the attachment and simply use the stroller now with the little one sitting in front and the older one either standing on the platform or sitting on the little back seat.
My older daughter never really liked strollers past the time she could walk on her own so I thought the sit and stand would be a good option. We also got a double jogger because once her little sister was born and getting rides, the older one decided she wanted to sit too! :)
Good luck!

Our second daughter was born right after our first turned 2. We had looked into double strollers and sit and stand strollers, etc but they were all so big. After a lot of thought I purchased an Ergo baby carrier and whenever we went out we used the stroller for big sister and the carrier for baby. It kept my hands free to keep up with my 2 year old and made shopping, etc so much easier as I was only dealing with a 2 year old strapped in a stroller or walking holding my hand. Also when we go to the grocery store - 2 year old sits in the shopping cart, baby in the carrier and I can get my shopping done!

They make a lot of configurations. I would go to someplace big, like Babies R Us or Great Beginnings and see what's on the rack. Test it out and see if your son will stand where he needs to.

I have a Baby Trend Sit n Stand, and it works great for my baby and 3 yo. It has an attachment bar that goes on the front so you can use it with an infant car seat, or the baby can sit in the seat up front. My 3 yo loves the "big girl" seat on the back that she can get in and out of on her own. It's been perfect for us!

I have the Baby Trend Sit and Stand. It accomodates an infant car seat in the front and once the baby is old enough, the carseat attachment is replaced by a snack tray. It also has the stand/sit platforms on the back. The only problem is that it is very hard to maneuver and the basket is large but hard to get to. If I had to do it all over, I would have just bought the platform attachment for my existing Graco stroller.