My son, at three and a half is nearly 45" tall. We live in an urban area and our favorite activity is going to different parks, museums, etc. Sometimes we cover 5 miles in a day on foot. That's a lot for little legs -- and well, a lot for someone with the maturity of a 3 - 5 year old.
In a few months we're expecting another baby (a girl). I need a stroller that will fit both of them...and will accommodate his height. He weighs about 40 pounds.
(To non-urban Mom's, strollers here are like cars for people in the burbs . It may seem crazy wanting a stroller for a four year old, but lots of my friends keep a stroller until the kids are five -- or more! )
All my city friends have phil & Ted doubles.
http://www.philandteds.com/upload/index.php/en/productsus...
And my 5 and 3 year old ride in in it comfortably with plenty of leg room even in the back.
I'd find a sit and stand stroller. That way you can have the baby in the front and your son can be on a seat in the back or he could stand and its easy for him to get in and out. The back does have a buckle.
I do know what you mean about needing a stroller. I got the nastiest look from someone once because I had my son, 4 at the time, in a stroller. I smiled and went on my way.
We have a Phil & Ted's and really love it for walks to the park, etc. It has large wheels and the seat holds up to 55 pounds. I too had a hard time finding a stroller that could accomodate a taller child...my daughter is also tall for her age but fits well in the seat. You can buy a back seat when the new baby comes. It reclines a little but works best once they are 4-6months (and have some neck control) It keeps the footprint of a single stroller when the back seat is in place and rides nicely on sidewalks.
I suggest the BumbleRide Indy Twin. My son is extremely tall too. It's a side by side but fits through all doorways nicely. Its amazing. Easy to push. Easy setup and take down as well. Good luck!
We use the Joovy Caboose. It is great in the city, as narrow as a single stroller and not so long that you can't weave in and out of aisles when shopping. It takes the cracked sidewalks just fine. My daughter (almost 6) is 46 inches and 45 pounds and is the sit or stand rider in back. My son (almost 3) is the front rider and it still work at 36 inches for him. We tried real hard to get rid of the stroller for our oldest, but just yesterday we did 7 miles walking to Navy Pier and back....that is too much to expect of her. The only downside is the storage space...very small!
I second the Bumbleride Indy Twin. My son is quickly following in his 6'7" dad's footsteps and every double we sat him in he was already grazing the tops. The Bumbleride has at least another inch before he hits the top of the seat. It's heavy but super easy to steer, great storage and I like how the shades detach from the back and can move forward - those came in really handy at the sweltering zoo the other day!! If you look at babygizmo.com they have really great stroller reviews with videos!
We have a single person MaClaren and it works great for taller kids and I think it's very sturdy for walking. We've even taken it on a farm in the dirt for a pumpkin picking. They do make double strollers too.
You have 2 options the phil and ted's or the baby jogger city elite. We decided on the city elite because we did not like putting one kid under the other one. My sons are 7 months and 4 years. My 4 year old is at least 42 inches tall and 42 pounds. WE bought the 2009 model and saved about 200 dollars . i hope that helps.
My 3 yr old daughter is also tall and I have a 1 yr old. I bought a Maclaren double umbrella stroller when my son was an infant and LOVE IT!!! My daughter seems pretty comfortable in it too. It maneuvers well, fits through a standard size doorway, is relatively light weight, and is easy to fold/unfold (I can almost do it with 1 hand). It will accomodate an infant with some inexpensive modifications like one of those head supports used in the car seats and for comfort some pads that wrap around the harness straps. My son was riding in it (comfortably and safely)at around 1 month. My 3 yr old even fell asleep in it the other day while on a walk. Also it folds up small enough to fit in the trunk of my Volkswagon Jetta!!!! It's not super pricey like some of the other double strollers out there and you can get it at Babies R Us. Good Luck! :)
