New York City
United States
Americas
NYC is challenging — street level is fine, but the subway will break you.
Best stroller: Compact
Mexico
Cancún is purpose-built for family holidays — flat resort strips, excellent beaches, and Mexican warmth toward children.
This city is stroller-friendly. Compact strollers work best.
📋 The Bottom Line
Cancún and the Riviera Maya represent Mexico's most family-friendly holiday region, purpose-built around resort tourism. The Hotel Zone is completely flat with modern infrastructure, beautiful beaches, and world-class family facilities. Mexican culture absolutely adores children — you'll receive incredible warmth everywhere. The challenges are some crowded resort areas, intense heat, and the need to stay within tourist zones. However, the resort areas are designed to be stroller paradise, with everything accessible and family-focused.
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
Share a tip to help other parents navigate the city. Your experience could save someone a tough day!
Share Your Tip