New York City
United States
Americas
NYC is challenging — street level is fine, but the subway will break you.
Best stroller: Compact
Aruba
Aruba's capital is flat, modern, and resort-friendly — one of the best Caribbean stroller cities.
This city is stroller-friendly. Lightweight strollers work best.
📋 The Bottom Line
Oranjestad is a compact, flat city with modern infrastructure that makes strolling surprisingly easy. The main shopping streets and waterfront areas are well-paved with good sidewalks. Resort areas like Palm Beach have excellent paths. The main challenge is limited public transit — you'll need a rental car or taxi to get between areas. Arubans are extremely family-friendly and welcoming.
Smooth, paved paths
Flat and easy
Limited accessible options
Elevators hit-or-miss
Good facilities in main areas
Manageable, some busy spots
Locals love kids!
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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