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
Cuba
Havana
48/100Challenging🌱 Limited data
Havana is incredibly atmospheric but challenging — colonial cobblestones everywhere, though Cuban warmth toward families is extraordinary.
🎒✅
Bring both
This city needs different solutions for different areas.
Key Factors
- •Mixed terrain requires flexibility
- •Old Havana entirely
Watch Out For
⚠️Use carrier in steep/narrow areas
Carrier Recommended
🎒Old Havana entirely - colonial cobblestones throughout
📋 The Bottom Line
Havana is one of the world's most atmospheric cities, but colonial-era infrastructure makes it tough for strollers. Old Havana is entirely cobblestoned with narrow streets and uneven surfaces. However, Cuban culture absolutely adores children — you'll receive constant offers of help, and families are central to Cuban society. The Malecón seawall provides flat coastal walking, and newer areas like Vedado have wider streets. The key is embracing a slower pace and preparing for infrastructure challenges.
Quick Facts
Overall Score48/100
Best StrollerRugged
Biggest ChallengeOld Havana entirely
Data Quality🌱 Limited data
Gear Recommendations
- 🎒Rugged stroller with excellent suspension absolutely essential
- 🎒Air-filled tires for cobblestones
- 🎒Carrier strongly recommended for Old Havana exploration
- 🎒Sun shade critical (Caribbean sun is intense)
Score Breakdown
Terrain20%
4/10Slopes20%
6/10Transit12%
3/10Elevators12%
3/10Facilities12%
4/10Crowding12%
5/10Friendliness12%
9/10Neighborhood Guide
🟢 Where It's Easy ✓
- •Malecón seawall - flat coastal promenade, sunset gathering place
- •Vedado district - wider 1950s streets, somewhat more accessible
- •Hotel areas - modern facilities, better infrastructure
- •Revolution Square - open, flat, spacious (though not family-focused)
- •Some beach areas - flat coastal access outside city center
🟡 Where You'll Struggle ⚠
- •Old Havana entirely - comprehensive cobblestone coverage
- •Most historic areas - colonial infrastructure, uneven surfaces
- •Public transport - very limited and challenging
- •Infrastructure generally - challenging conditions throughout
🎒 When to Bring the Carrier 👶
- •Old Havana entirely - colonial cobblestones throughout
- •Plaza de Armas area - historic, uneven, crowded
- •Narrow residential streets - traditional Cuban architecture
- •Some traditional markets - packed, no space for strollers
Parent Wisdom
❌ What Parents Wish They'd Known
- ✕Old Havana expecting any smooth surfaces (it's all cobblestone)
- ✕Relying on public transport (very limited options)
- ✕Not experiencing Cuban family culture (incredibly welcoming)
- ✕Missing the Malecón (it's the most accessible area)
- ✕Underestimating infrastructure challenges (they're significant)
⭐ Parent-Recommended Spots
- ★Malecón seawall walk - flat, atmospheric, essential Cuban experience
- ★Cuban music venues - incredibly welcoming to families
- ★Traditional Cuban restaurants - families are central to Cuban culture
- ★Hotel rooftop terraces - accessibility with great Old Havana views
- ★Beach day trips - flat coastal relief from city cobblestones
Similar Destinations
Other cities you might want to explore
38Challenging
San Francisco
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
62Doable with Planning
Lisbon
Portugal
Europe
Lisbon is doable with planning — bring rugged tires for the cobbles.
Best stroller: Rugged
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