Not only is it the Caribbean’s most modern metropolis, it also contains the region’s oldest history!

 As the First European City in the Americas,  SD beckons with its cobblestone roads, waterfront esplanade and centuries-old history. To explore this wondrous city, mix and match the activities and attractions below to create your personal weekend itinerary.

1. Explore history on a walking tour of the Colonial City.

Dive into the past by exploring Santo Domingo’s Colonial City—the first European settlement of the Americas and a UNESCO World Heritage Site.

Wander by foot, Segway, electrical scooter or bike and let yourself get lost in a maze of charming cobblestone streets that date back to the 16th century. Or browse the souvenir shops on Calle el Conde, the first commercial street in the new world. Another must visit, Monasterio de San Francisco, the first monastery in the New World, constructed in 1556. Along the way, stop to admire the Gothic and Plateresque architecture of the first cathedral of the Americas, built between 1510 and 1540. You can also hire a local guide to show you the most notable and Instagram-worthy sites in the area.

Ruinas Nicolás de Bari

2. Ride the Chu Chu Colonial Train.

One of the best ways to get the lay of the land in the Colonial City is by hopping aboard the Chu Chu Colonial Train. This 45-minute train ride around the historic center offers a scenic and sweeping view of the old neighborhood. It’s an ideal option for families or anyone ready to rest their legs while enjoying the ambiance of the Colonial City.

3. Spend a day museum hopping

Go deeper into the history of the city by spending an afternoon exploring the cities museums, Plaza de la Cultura is a great place to start. Here, you’ll find the city’s most important museums, including the Museo del Hombre Dominicano, the Museum of Modern Art, the Museum of Natural History and the National Library.

Another can’t miss is Museo de las Casas Reales, The Museum of Royal Houses, which was used as the Spanish Governor’s Royal Court in the 16th century—home to the governor’s palace, the treasury, and the courts of law. Today, the museum offers an informative overview on the history of the Dominican Republic from the colonial period in 1492 to the days of slavery, and the country’s first independence from Spain in 1821. Today, the museum highlights the history, life, and customs of the Spanish colony in the Dominican Republic. Even if you don’t go in, the building itself is a stunning display of colonial architecture, punctuated by vast Spanish courtyards.

For an overview of life underwater, head to The Museum of Royal Atarazanas (MAR), a space that houses the most important underwater archeology exhibition in the Dominican Republic and throughout the Americas. MAR opened in 2019 with the goal of publicizing a valuable collection of historical and cultural assets extracted from Dominican coasts. Its museography is developed through a narrative that tells stories of more than a dozen historical shipwrecks between the fifteenth and nineteenth centuries.

For family fun, add  Museo Infantil Trampolín to your Santo Domingo itinerary. Designed to entertain and educate children and their families, the Museo Infantil Trampolín is marked by a large, beautifully kept central courtyard adjacent to its entrance. Indoors, nine rooms showcase major educational themes ranging from the Planet Earth and ecology, to human beings, weather systems, and various aspects of Dominican culture.

But be sure to check museum websites in advance to see which exhibits are on display so you can plan your perfect museum route.

Museo de las Casas Reales

4. Plan a picnic at the National Botanical Garden.

Reconnect with nature without leaving the city. Santo Domingo is home to the largest botanical gardens in the Caribbean, with more than 400 acres of nature preserves. Admire hundreds of species of orchids, trees native to the island and countless species of flowers. Bring a picnic lunch and relax in the Japanese garden where you can find your Zen amid the manicured lawn and lakes.

5. Enjoy the atmosphere in the Plaza de España.

This picturesque plaza in the Colonial City is home to numerous bistros with outdoor terraces and gorgeous views of the historic neighborhood. Discover a different character in the plaza at each time of day, whether you pause to sip a morning coffee in the plaza or visit on the weekends when free concerts and festivals fill the square.

6. Stroll along the Malecón.

For a walk to remember, head to the seafront Malecón boardwalk. Enjoy a cocktail while watching the waves roll in, pick up a snack from a local street vendor or simply enjoy some quality peoplewatching. By day, the Malecón is bustling with joggers, bikers and roller bladders. In the evenings, you’ll often find live music and a bustling nightlife scene.

7. Venture Through Parque Nacional Los Tres Ojos.

Just five miles east of Santo Domingo, Los Tres Ojos National Park is a beautiful nature break from the city and offers a solid glimpse of the Taino’s underground caverns once used for refuge or rituals. A winding entrance staircase leads to a series of caves, with pathways hugging three freshwater, iridescent blue lagoons or “eyes” as the Taino used to call them for their oval shapes. A fourth lagoon is accessible via a small wooden barge, revealing a gorgeous, open-air scenery of water and a rocky landscape covered in lush vegetation all around. Keep an eye out for petroglyphs and pottery shards!

8. Pick Up Local Souvenirs at Mercado Modelo.

Built in 1942, Santo Domingo’s largest market is also one of the city’s first tourist venues. Standing tall on Avenida Mella, a commercial hub on the northern edge of the Colonial City, this indoor and outdoor shopping bazaar is a must-visit. Up a series of bright yellow painted steps, you’ll find an indoor maze of small, organized shops pulling you into a world of all things Dominican—from woodcarvings and paintings, to amber jewelry, and papier mâché carnival masks. Venture to the back of the market, where street side stalls are brimming with the DR’s tropical fruits, vegetables, and seafood, and locals shop and haggle daily.

9. Immerse Yourself in the KahKow Experience

Experience chocolate in a way you have never seen before. Operated by one of the country’s top cacao exporters, the KahKow Experience, is a part museum, part chocolate factory—located in the heart of historic Calle Las Damas—which offers a comprehensive and delicious glimpse into the DR’s thriving cacao industry!

The multimedia presentation includes a holographic theater, as well as a guided audio walk through the various rooms and visual exhibits, explaining the process of chocolate from tree to pod, and tablet. The tasting room features various types of chocolates, from white to dark that you can sample to your heart’s content. A chocolate making factory sits inside a glass-enclosed room at the center of the building’s courtyard, where workshops are offered for those who sign up in advance. Learn more about their tours 

10. Go Food Truck Hopping All Over The City

Explore the different food trucks parks located all over the city that offer creative Dominican and international cuisine, such as the Food Truck Village at Gustavo Mejía Ricard, Food Truck Park at Nuñez de Cáceres, Garden Food Trucks at Abraham Lincoln, Terraza Food Truck Park at Rómulo Betancourt, Food Truck Town at the 27 de Febrero, Food Truck Malecón, Food Truck World at the Independencia avenue and El Patio Culinario at Padre Billini street.