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
Dominican Republic
Santo Domingo
56/100Doable with Planning🌱 Limited data
Santo Domingo mixes colonial history with Caribbean energy — the Zona Colonial has cobblestones, but Dominican warmth is infectious.
🎒✅
Bring both
This city needs different solutions for different areas.
Key Factors
- •Mixed terrain requires flexibility
- •Zona Colonial
Watch Out For
⚠️Use carrier in steep/narrow areas
Carrier Recommended
🎒Zona Colonial entirely - extensive colonial cobblestones
📋 The Bottom Line
Santo Domingo is the oldest European city in the Americas, with the Zona Colonial featuring stunning but challenging cobblestone streets. The modern areas have much better infrastructure, and the Malecón waterfront provides flat, beautiful strolling. Dominican culture is incredibly family-focused — children are adored, and you'll receive constant warmth and offers of help. Merengue music, delicious food, and genuine hospitality make the infrastructure challenges worthwhile for cultural immersion.
Quick Facts
Overall Score56/100
Best StrollerRugged
Biggest ChallengeZona Colonial
Data Quality🌱 Limited data
Gear Recommendations
- 🎒Rugged stroller with excellent suspension for colonial cobblestones
- 🎒Air-filled tires essential for rough stone surfaces
- 🎒Carrier recommended for Zona Colonial exploration
- 🎒Sun shade critical for Caribbean heat
Score Breakdown
Terrain20%
5/10Slopes20%
6/10Transit12%
5/10Elevators12%
5/10Facilities12%
6/10Crowding12%
5/10Friendliness12%
9/10Neighborhood Guide
🟢 Where It's Easy ✓
- •Malecón waterfront - flat seaside promenade, perfect for strolling
- •Modern Santo Domingo - Piantini area, wide streets, shopping
- •Plaza de la Cultura - modern cultural center, accessible
- •Hotel zones - international standards, family facilities
- •Modern shopping centers - air-conditioned, family-friendly
🟡 Where You'll Struggle ⚠
- •Zona Colonial - beautiful but entirely cobblestoned
- •Traditional markets - overwhelming crowds, narrow stalls
- •Some residential hills - challenging terrain
- •Downtown traffic areas - busy, challenging crossings
🎒 When to Bring the Carrier 👶
- •Zona Colonial entirely - extensive colonial cobblestones
- •Traditional markets - Mercado Modelo, extremely crowded
- •Some steep residential areas
- •Narrow historic streets throughout old city
Parent Wisdom
❌ What Parents Wish They'd Known
- ✕Zona Colonial expecting smooth surfaces (it's all cobblestone)
- ✕Traditional markets with any stroller
- ✕Not experiencing the Malecón (perfect for families)
- ✕Missing Dominican family food culture (incredibly welcoming)
- ✕Underestimating heat and humidity intensity
⭐ Parent-Recommended Spots
- ★Malecón seaside walk - flat, breezy, beautiful Caribbean setting
- ★National Palace - impressive architecture, accessible grounds
- ★Modern shopping centers - air-conditioned relief, family dining
- ★Traditional Dominican restaurants - incredible hospitality, family-focused
- ★Alcázar de Colón - historic (use carrier), fascinating colonial history
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
71Stroller-Friendly
Barcelona
Spain
Europe
Barcelona is stroller-friendly with planning — beach areas great, Gothic Quarter tricky.
Best stroller: Compact
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