Bugaboo Bee 5
I know what you're going to say, an $800 stroller, you've got to be kidding me? But really, it's worth every penny. Plus it's one of the few things you will use all the way until Pre-School! I got mine second hand for half the price and in great condition, so don't be deterred by the cost.
So why this stroller? I was looking for something light so that I could carry it with one hand and compact since there never is enough room in the trunk. But I also wanted something that my infant car seat could easily clip into. A big bonus is that you can open it with one hand and one foot, you just step on the pedal and pull until the frame snaps into place. You do need two hands to close it, but it's one quick motion.
The best part is it's very customizable, so you can find exactly what matches your style. You could spend an hour playing with their online design tool to find the seat fabric, sun canopy fabric, chassis color, grips, wheel covers and bassinet (optional) that's perfect for you.
Plus there is a ton of accessories so if you must have a Phone or Cup Holder you can add one, or if you have an older toddler you can use the Comfort Wheeled Board. Ours came with the Breezy Sun Canopy and we love it. In Honolulu, a shade with SPF 50 is a lifesaver and I love that the bug net covers the entire seat while letting the breeze in to keep it cool. We also have the Compact Travel Bag to protect it when traveling.
Find it here.