Editor’s note: I spent two full weeks in Santo Domingo a few years back, and while the city wasn’t as well kept up as the historic portions of San Juan or Cartagena, I found my time there to be incredible. (You can read my guide here.) In this piece, Sam – in a way only he can – sums up the spirit of a place perfectly. For more of Sam’s adventures, click here to visit his index page.
In 2018, I went to Havana, Cuba, which was one of the most incredible, magical cities that I have been to. In particular, the colonial old town with all its history truly amazed me. This trip sparked a desire to see the two other great colonial capitals of the Caribbean, Santo Domingo, Dominican Republic and San Juan, Puerto Rico. In 2022, I had the opportunity to choose to visit one of these spots, but decided on Puerto Rico, feeling a need to support the island after it had been devastated by a hurricane and largely neglected in its recovery efforts by our government. Though different, San Juan’s colonial city gave me the same feelings that I had had when visiting Havana. That left the Dominican Republic, which I got to visit in 2025.
Santo Domingo is by far the largest city in the Caribbean with a metropolitan population of 4.7 million inhabitants (the next closest city is Havana with 2.7 million). While Santo Domingo offers a ton in terms of nightlife, dining, and professional sports (especially baseball), this city has easily some of the worst traffic that I have ever experienced. After a lengthy commute, I arrived in Santo Domingo’s Colonial Zone. This 1 square kilometer area is the oldest European-founded colonial settlement in the Americas, with the city founded in 1496 by Bartholomew Columbus, the brother of Christopher Columbus, who had arrived on the island in 1492. The Columbus brothers decided to create a town here rather than the Bahamas and Cuba, where they had landed previously, as on the island of Hispaniola, the native Taino people had greeted them not with hostility, but with gold in friendship. Many of the buildings in the Colonial Zone are among the oldest in the Americas and where explorers like the Columbus brothers, Hernan Cortes, conqueror of the Aztecs and Mexico, and Francisco Pizarro, who conquered the Incas in Peru, lived. The entire area, which overlooks both the Caribbean Sea and the Ozama River, is a UNESCO World Heritage Site.
A good place to begin your tour of the Colonial Zone is by walking down the Calle de las Damas (the Ladies’ Street), named for the elegant women who would walk down it hundreds of years ago. Take time to explore the Colonial Zone. I took an organized tour and found it to be too short and also too focused on trying to get us to buy things from souvenir shops, likely for the tour company to get commission. The area has over 300 historical buildings and sites, so it is not realistic to see everything. Calle de las Damas was the first paved road in the Americas. On it is a museum called the Museo de las Casas Reales, which is dedicated to showing the life of the early Caribbean colonists and was the first headquarters of the Spanish in the Americas. In front of the museum is a sundial built in 1753. The most famous building in the Colonial Zone is likely the Alcazar de Colon, which was the palace of Diego Colon, son of Christopher Columbus. Nearby is a building that Christopher Columbus stayed in. There is a park that is well shaded in front of numerous restaurants and shops called Parque Colon that has several street vendors selling jewelry with the light blue gem Larimar, which is only found in the Dominican Republic. The park contains a statue of Christopher Columbus in the middle as a subservient indigenous man kneels at Columbus’s feet and is writing his name into the base of the statue. Behind the statue is the first cathedral in the Americas.
The Cathedral Basilica of Santa Maria la Menor was built between 1504 and 1550 by orders of the Vatican. Like the Alcazar de Colon and other buildings of the time, it is built in Gothic style architecture. The cathedral only costs about $1.50 to enter and an additional dollar for an audio guide. It has been visited by popes and is the burial place of several prominent figures. There are several altars with statues and paintings in the cathedral. The ribbed vault nave is beautiful and unique. Being a cathedral basilica, it is a large building, but not larger than the grand cathedrals of Europe or built elsewhere in Latin America later. The cathedral was modeled after the cathedral in Seville and there is a tomb in the Cathedral Basilica of Santa Maria la Menor where Columbus’s remains were entombed until the 1790s when the French took over the island of Hispaniola; the remains were then moved to Havana. After the Spanish-American War, part of the treaty with the Americans involved Columbus’s remains to be relocated to the Seville Cathedral. While we know that Columbus’s remains are at least partially in Seville as was confirmed by a DNA test, both Havana and Santo Domingo claim to also have remains and burial sites of Columbus still, but the Spanish government will not permit them to be tested so that they can claim to have the only remains. In Santo Domingo, Columbus’s remains are supposedly buried at the Faro a Colon, a massive mausoleum with an almost Soviet-style brutalist architecture that beams light into the sky at night. Though it is not in the Colonial Zone, it is visible from it.
With Santo Domingo and the Dominican Republic, an important and dark part of the nation’s history is the three decade rule of the dictator, Rafael Trujillo. During Trujillo’s rule, he called Santo Domingo “Ciudad Trujillo”, and in the Colonial Zone you can still see “Ciudad Trujillo” on manhole covers. One of the projects of Trujillo was the National Pantheon, which was originally an 18th century Jesuit convent. Trujillo had it remodeled to be a burial place of national heroes, including for himself one day. While the National Pantheon did become an eventual place of burial for many Dominican national heroes, Trujillo, who was assassinated in 1961, was not among them. Trujillo’s son buried his father in exile in Madrid, Spain. Ironically, some of those involved in the plot to assassinate Trujillo are buried within the National Pantheon, and there is an honor guard who stands guard at the site with an eternal flame. After touring the Colonial Zone, you will certainly work up an appetite. Head to Buche Perico, an upscale restaurant in the Colonial Zone that has a beautiful dining space with a greenhouse.
Beyond Santo Domingo’s Colonial Zone, there were not too many actual points of interest in the Dominican Republic compared to the many of Cuba and Puerto Rico. Like Havana, the city has a beautiful Malecon (promenade) along the sea that makes for beautiful walks and jogs. Though I did not head to the northern Atlantic Coast, the cities of Puerto Plata and Sosua have historical sites including a Jewish museum commemorating the story of the 800 Jewish refugees that were taken in by the Dominican Republic during World War II. The northern Samana Peninsula is also famous for humpback whale watching in the early spring. If I head back to Dominican Republic, I will check out this area. However, there is a reason that this country of 12 million people has 11 million visitors a year, more than anywhere else in the Caribbean, and that is its pristine white sand beaches and golf resorts.
Punta Cana is the most popular destination, with its sandy cape lined with hotels. However, I went to the town of La Romana, about 90 minutes east of Santo Domingo and roughly the halfway point between the capital and Punta Cana. This resort-filled town has beautiful beaches and all-inclusive hotels. Nearby is the Chavon River, which one can do boat trips on, and the town of Altos de Chavon, a theme town that requires paid entry that was designed to look like a medieval Italian city. The most popular excursions are the small Catalina Island near La Romana and the larger Saona Island, which is part of the East National Park. There are many companies that run full day tours to Saona Island which involve stopping at starfish-filled area to swim (do not pick up the starfish as it will kill them), snorkeling, a dance boat, and a couple hours on the island with a buffet lunch. Saona Island with its massive forest of palm trees, white sand beaches, mangroves, and Caribbean blue water looks like a desktop background and is a slice of paradise. The only thing that makes the experience more perfect is getting a massage on the beach from one of the onsite masseuses.
At the end of the day, I was surprised at how different my experiences were between the Dominican Republic and Puerto Rico, but it was not that one was better than the other. If you want a more developed tourist infrastructure, white sand beaches with all-inclusive resorts, and you just want to relax, go with the Dominican Republic. If you want more sightseeing, things to do, and a more organized experience in the Colonial Zone, head to Puerto Rico. While I was slightly frustrated that it did not feel that the Dominican Republic had as much to offer as Cuba or Puerto Rico, I had to remind myself that playing on some of the most beautiful beaches that I have ever been to or splashing in the pool with my daughters was about as good as it gets.
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