Bugaboo Kangaroo Tandem Stroller ($1448)
The Bugaboo Kangaroo excels in all of the criteria that are important to me for a double stroller. First, it's a tandem stroller that's actually easy to push. In testing double strollers, I've found that the trade-off for the slim design is that tandems can sometimes feel nearly impossibly for me, as a 5'2 person, to easily push the 100 lb load (between the stroller and toddlers.) It's a next level of panic when I start to go on walk with a new stroller and then realize it can't handle the turns, uneven sidewalk, or gritty snow. I've had no such issues with the Kangaroo. It has a beautifully smooth stroll and maneuverability.
It is a dream stroller if you're frequently going to be loading it into a car thanks to the one handed fold, width of 24.4 inches, and its comparatively light weight at 28.6lb. While it does have a steep price tag, it's versatile, with over 20 configurations to accommodate newborn to big kids. One configuration that stood out to me is the ability to have the bassinet in the upper position, so you can keep your eye on the younger baby, with the larger child in the lower position. It's convertible and can be used as a single stroller and can also use a comfort wheeled board ($140) to accommodate three children. The main seat can carry up to 50lbs while the sibling seat can carry up to 40 lbs when in the lower position.
