New York City
United States
Americas
NYC is challenging — street level is fine, but the subway will break you.
Best stroller: Compact
Uruguay
Montevideo offers relaxed South American charm with excellent coastal access — the Rambla waterfront is perfect for families.
This city is stroller-friendly. Compact strollers work best.
📋 The Bottom Line
Montevideo is one of South America's most relaxed and family-friendly capitals. The famous Rambla (waterfront promenade) stretches for kilometers and provides flat, beautiful strolling along the Rio de la Plata. The city is largely flat with some gentle hills, and Uruguayan culture is laid-back and genuinely welcoming to families. The European influence creates excellent café culture, and the pace of life is refreshingly unhurried. Infrastructure is good by South American standards.
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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