55Doable with Planning
New York City
United States
Americas
NYC is challenging — street level is fine, but the subway will break you.
Best stroller: Compact
Puerto Rico
San Juan
71/100Stroller-Friendly📊 Medium confidence
San Juan combines Spanish colonial charm with American accessibility standards — Old San Juan is cobblestoned, but modern areas excel.
✅
Bring your stroller
This city is stroller-friendly. Compact strollers work best.
Key Factors
- •Generally manageable
- •Compact stroller recommended
Watch Out For
⚠️Old San Juan
📋 The Bottom Line
San Juan offers the best of both worlds: stunning Spanish colonial architecture with American infrastructure standards. Old San Juan has challenging cobblestone streets but incredible atmosphere, while Condado, Isla Verde, and modern areas provide excellent accessibility. Puerto Rican culture absolutely adores children — family is central to everything. American accessibility laws apply, so many attractions meet high standards. The beaches are flat and perfect, and the year-round tropical climate is ideal for families.
Quick Facts
Overall Score71/100
Best StrollerCompact
Biggest ChallengeOld San Juan
Data Quality📊 Medium confidence
Gear Recommendations
- 🎒Rugged stroller recommended for Old San Juan cobblestones
- 🎒Compact option works for modern areas and beaches
- 🎒Sun shade absolutely critical (tropical Caribbean sun)
- 🎒Beach wheels helpful for sandy coastal access
Score Breakdown
Terrain20%
7/10Slopes20%
6/10Transit12%
7/10Elevators12%
7/10Facilities12%
8/10Crowding12%
6/10Friendliness12%
9/10Neighborhood Guide
🟢 Where It's Easy ✓
- •Condado Beach area - flat, modern, perfect resort infrastructure
- •Isla Verde - modern beach district, accessible, family-focused
- •Modern San Juan - wide streets, shopping centers, accessible
- •Beaches - flat coastal access, beautiful Caribbean setting
- •Luis Muñoz Rivera Park - flat, green, playground
🟡 Where You'll Struggle ⚠
- •Old San Juan - beautiful but entirely cobblestoned
- •El Morro and fortress areas - historic military architecture with steps
- •Some traditional barrios - narrow, hilly streets
- •Cruise ship arrival crowds - overwhelming in Old San Juan
🎒 When to Bring the Carrier 👶
- •Old San Juan - extensive colonial cobblestones throughout
- •El Morro fortress - steps, fortification walls
- •Some traditional neighborhoods - narrow streets
- •Crowded areas during cruise ship arrivals
Parent Wisdom
❌ What Parents Wish They'd Known
- ✕Old San Juan expecting flat modern streets
- ✕Fortress tours with stroller (use carrier)
- ✕Cruise ship days in Old San Juan (extremely crowded)
- ✕Not exploring modern beach areas (they're excellent)
- ✕Underestimating Caribbean UV intensity
⭐ Parent-Recommended Spots
- ★Condado Beach - flat, safe, beautiful, perfect for families
- ★El Yunque Rainforest (accessible areas) - waterfalls, nature, educational
- ★Modern shopping centers - Plaza Las Américas, fully accessible
- ★Camuy Caves (accessible sections) - natural wonder, family-friendly tours
- ★Traditional Puerto Rican restaurants - incredible family hospitality
Similar Destinations
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San Francisco
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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
78Compact Stroller Paradise
Amsterdam
Netherlands
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Amsterdam is stroller paradise — flat terrain and everyone yields to wheels.
Best stroller: Compact
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