We've got a five year old, three year old and 10 month old. We also have four strollers and none of them, I think, have been ideal.
The first one we got was the Graco combo dealie that came with the bucket and the base that goes in the car. It worked great when we only had one kid, but it was really bulky and took up most of the trunk of our car.
We got a small umbrella stroller when we were on vacation and the kid was a bit older. It did fine for short trips, but was much less comfortable and not as convenient for storage or for letting the kid nap.
When the second kid came along, we got a Joovy Sit n Stand. It's probably the best of the bunch. The bucket seat clipped into the front when the youngest needed it and still had a spot for our oldest to sit. It was lighter than the Graco monster and actually took up less room in the trunk. It had a lot of storage too and handled pretty well. As far as double strollers go, it did very well at the mall and on walks outside provided you stayed on the beaten path.
We also have a double jogging/bike stroller made by Bell or something that kind of looks like a Chariot. It's clearly not a Chariot. We got it second hand so the price was right and, for how much we use it, it works well enough for long walks/jogs and off road. It's too wide and bulky to use in a mall or anything like that though.
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