New York City
United States
Americas
NYC is challenging — street level is fine, but the subway will break you.
Best stroller: Compact
United States
Orlando is purpose-built for families — Disney World sets the global standard for stroller accessibility.
This city is stroller-friendly. Compact strollers work best.
📋 The Bottom Line
Orlando is the world's premier family destination, purpose-built around Walt Disney World's accessibility standards. The theme parks, hotels, restaurants, and attractions are designed with families in mind. Disney World pioneered many accessibility features now used globally. The flat terrain, comprehensive stroller rental systems, and family-first culture make this incredibly easy. The main challenges are crowds (especially summer/holidays) and Florida heat, but the infrastructure is unmatched anywhere in the world.
Other cities you might want to explore
United States
Americas
NYC is challenging — street level is fine, but the subway will break you.
Best stroller: Compact
United States
Americas
San Francisco's extreme hills make it one of the toughest US cities for strollers — flat areas exist but you have to find them.
Best stroller: Rugged
Netherlands
Europe
Amsterdam is stroller paradise — flat terrain and everyone yields to wheels.
Best stroller: Compact
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