Hodelpa Nicolás de Ovando

Sandwiched between the glittering water of the Caribbean Sea and the oldest cobblestone street in the new world, the Hodelpa Nicolas de Ovando is a colonial jewel. Set in three castle-like stone residences built in 1502, this historic hotel includes the original home of the city’s founder, Governor Nicolás de Ovando. With its history-steeped walls and parapets overlooking the waterways, this is a dream stay for anyone looking to explore Santo Domingo away from the fray.

Each of the near-hundred guest rooms (and four VIP suites) is lavishly restored to show off the hotel’s rich Spanish colonial heritage. Five-star comforts have been carefully integrated to preserve the historic ambiance. Take some time to wander the lavishly-furnished stone passageways and parapets, enjoy the view of ships winding up the Rio Ozama, and immerse yourself in five centuries of Caribbean colonial intrigue.

Breakfast is served on the Spanish colonial terrace overlooking the colonial district. Friendly staff lay out a buffet of artisanal baked-on-premised bread, fresh fruit, omelets, French pastries, Nordic-inspired salted fish options alongside smoothies, green juices, and of course - delectable Dominican coffee.

If you’re looking for exquisite examples of authentic Dominican cuisine, there’s no need to leave the hotel. Set in the Bartolome de las Casas Courtyard, Restaurante 1502 dishes up enticing Latin specialties such as sancocho, churrasco steak and pinchos alongside aged cognac and fine wines. Alternatively, head to the in-house bar for local staple mofongo, or stroll out into the colonial district for tacos and tequila at Onno’s. For a sweet treat, head to Paletas Bajo Cero for handcrafted gourmet ice cream.

Open 8am to 11pm, the hotel bar “La Taberna del Mojito” specialises in mojitos. You can lounge around the lavish colonial lobby, shade yourself in the arcade or dip your toes in the outdoor pool, walled by colonial facades and open to a vaulting blue sky.

For world-class tapas, cocktails, cigars and live jazz, head out into the colonial zone and follow the fabulous after-work crowd to Lulú.

This UNESCO-listed colonial building hides an outdoor pool, billiards table, fitness centre, laundry, concierge and valet service.

Dating back to the 1500s, the historic colonial zone is the oldest existing European settlement in the Americas and has UNESCO World Heritage status. During the day, the colonial zone is one of the top attractions in Santo Domingo, with several landmarks worth visiting including the Alcázar de Colón, Fortaleza Ozama, and Basilica Cathedral of Santa María la Menor. By night, the zone is full of lively cosmopolitan bars and attracts a chic crowd of locals and visitors dressed up for fine dining and cocktails.

Although there’s almost one hundred rooms, this is one of the most prestigious hotels in Santo Domingo, so you’ll want to book in advance to secure your preferred room.