Updated for 2026. This post originally recommended the Bugaboo Bee5 — a wonderful city stroller that Bugaboo has since discontinued. Its successor, the Bugaboo Dragonfly, is better in nearly every way, and after putting it through its paces on our own South End sidewalks, we're comfortable calling it the best city stroller in Bugaboo's current lineup.
Why the Dragonfly is built for city life
After 20 years of helping Boston families choose strollers, we've learned that city parents have a very specific checklist: it has to steer with one hand, fit through old brownstone doorways and tight store aisles, fold down small enough for a hatchback or a hallway closet, and survive brick sidewalks and curb hops without rattling apart.
The Bugaboo Dragonfly checks every box. It's the most comfortable everyday stroller Bugaboo makes, with an innovative compact fold that makes it easy to stash in a small apartment or car trunk. From day one you have multiple configurations: the included bassinet for the newborn months, then a reversible seat so your little one can face you (our favorite for the first year) or face out and take in the city. Add the Dragonfly car seat adapters and it becomes a full travel system with compatible infant car seats.
What about the rest of the Bugaboo family?
The Dragonfly isn't the right answer for everyone — that's exactly why we keep the whole Bugaboo lineup on our showroom floor:
- Bugaboo Butterfly 2 — the ultra-compact, one-second-fold travel stroller. If you're constantly hopping on the T, ducking into Ubers, or flying with a carry-on-sized stroller, this is the one to test.
- Bugaboo Donkey 5 — the classic side-by-side that converts from single to double in a few clicks, for families planning ahead.
- Bugaboo Kangaroo — Bugaboo's newer 2-in-1 single-to-double that handles rougher terrain, great if your weekends take you beyond the pavement.
Don't buy a city stroller you haven't pushed
Spec sheets can't tell you how a stroller feels over brick, or whether the fold really works with a baby on your hip. That's why we keep demo strollers ready to test in store at 58 Clarendon Street in Boston's South End. First-time parents especially: book a baby gear appointment and we'll walk you through the Dragonfly side-by-side with its competitors from Nuna, UPPAbaby, Cybex, and more — no pressure, just 20 years of experience helping families like yours.
Pairing it with an infant car seat? Every car seat purchased from us includes free installation by a certified technician. We're open Tuesday–Saturday, 10am–6pm — plan your visit or browse all our strollers online.