Amsterdam
Netherlands
Europe
Amsterdam is stroller paradise — flat terrain and everyone yields to wheels.
Best stroller: Compact
Portugal
Funchal is built on steep volcanic slopes — beautiful but a serious workout with a stroller. Use the cable car.
This city needs different solutions for different areas.
📋 The Bottom Line
Funchal is the charming capital of Madeira, built on dramatic volcanic slopes that rise steeply from the harbor. This is one of the hilliest cities you'll encounter — streets climb at angles that would make San Francisco blush. The old town (Zona Velha) has cobblestones, and most residential streets are steep. However, the waterfront promenade and marina area are flat and pleasant, the Lido area is more modern, and the Teleférico do Funchal cable car is a lifesaver for reaching the Monte area without destroying your legs. Madeiran people are extraordinarily warm and helpful — expect strangers to help you up steps without being asked.
Other cities you might want to explore
Netherlands
Europe
Amsterdam is stroller paradise — flat terrain and everyone yields to wheels.
Best stroller: Compact
Denmark
Europe
Copenhagen is designed for families — flat, accessible, and everyone loves kids.
Best stroller: Compact
United States
Americas
NYC is challenging — street level is fine, but the subway will break you.
Best stroller: Compact
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