This 500-Year-Old Neighborhood in the Dominican Republic Has Boutique Hotels, Rooftop Bars, and Cobblestone Streets

Santo Domingo’s Colonial Zone isn’t just the oldest neighborhood in the Americas — it’s one of the most vibrant urban districts in the Caribbean today. Set on the Dominican Republic’s southern coast, this UNESCO World Heritage Site blends centuries-old architecture with a lively street culture, world-class dining, and boutique hotels tucked inside restored colonial buildings. Whether you’re here for a weekend getaway or as part of a longer Dominican adventure, the Colonial Zone offers a walkable, story-filled escape that feels like stepping into another era — without leaving modern comforts behind.

Where History and Everyday Life Meet

Step through the stone gates of the Colonial Zone and you’re walking into the oldest European city in the New World — a living, breathing district where 500 years of history unfold in the rhythm of daily life. Here, the cobblestone streets are lined with Spanish colonial facades in pastel hues, wrought-iron balconies dripping with bougainvillea, and plazas where the scent of fresh coffee drifts from shaded cafés. It’s a neighborhood that invites you to slow down — to wander without a plan and let the stories reveal themselves.

The Oldest Landmarks in the New World

The Colonial Zone is home to some of the hemisphere’s most important historic sites. The Catedral Primada de América, completed in 1541, is the first cathedral built in the Americas — a masterpiece of Gothic and Baroque design. Nearby, Fortaleza Ozama has stood guard over the Ozama River since 1505, its thick stone walls whispering tales of pirates and colonial governors. Every corner seems to hide another relic: the 16th-century Monasterio de San Francisco, the Calle Las Damas — the first paved street in the Americas — and the Museo de las Casas Reales, which traces the history of Spanish rule in the Caribbean.

A Neighborhood Made for Walking

The Colonial Zone’s magic is best experienced on foot. You can stroll from the grandeur of Parque Colón, where the statue of Christopher Columbus presides over shaded benches, to the lively pedestrian strip of Calle El Conde, lined with shops, street vendors, and open-air cafés. Side streets beckon with hidden courtyards, quiet churches, and boutique hotels that open their heavy wooden doors to reveal lush gardens inside.

Cafés, Courtyards, and Nightlife

As day turns to evening, the Colonial Zone’s energy shifts. The aroma of Dominican coffee gives way to the clink of glasses as rooftops and courtyards fill with music. Sip a rum cocktail in a candlelit garden, savor mangu in a 17th-century building, or dance to live merengue under the stars. The district’s culinary scene blends tradition with creativity, with chefs reimagining Dominican classics alongside global flavors.

Where to Stay in the Colonial Zone

Billini Hotel — Set in a former 16th-century convent, Billini blends historic grandeur with sleek, contemporary design. Its stone walls and archways frame airy, modern interiors, while the rooftop pool and terrace offer sweeping views over the Colonial Zone’s tiled rooftops.

Hodelpa Nicolás de Ovando — Occupying the original home of the city’s founder, this property is a piece of history you can sleep in. With restored colonial architecture, courtyards shaded by mango trees, and rooms that open to the Ozama River, it’s an immersive stay in Santo Domingo’s past — with the comforts of a luxury hotel.

Kimpton Las Merceddes Santo Domingo — The newest arrival in the Zone, Kimpton brings its signature boutique flair to the Colonial Zone. Inside, you’ll find design-forward rooms, a rooftop lounge with panoramic city views, and dining that puts a modern spin on Dominican flavors, all just steps from the city’s most famous landmarks.

Casas del XVI — This collection of restored 16th-century homes transforms historic residences into private, luxurious sanctuaries. Each “casa” has its own personality, with curated art, handcrafted furniture, and attentive butler service. Guests can choose a single home or combine several for an ultra-private stay, all within walking distance of the Colonial Zone’s most iconic sites.

How to Get Here

Santo Domingo’s Las Américas International Airport is about 30 minutes from the Colonial Zone, with direct flights from Miami, New York, Atlanta, and other major U.S. cities – and a growing number of them. You can fly on JetBlue from Fort Lauderdale right now for as low as $206 roundtrip.

Taxis and rideshares are readily available, and once you arrive, you’ll want to explore entirely on foot.