fortaleza ozamaSanto Domingo, Dominican Republic doesn’t get nearly enough credit. It’s the oldest city in The Americas (est. 1496) and home to the first cathedral, university, castle, monastery, and fortress in the New World. If you knew that, good on ya, but I feel like every person we’ve told is as surprised as we were. Why is that? Maybe because it’s overshadowed by Punta Cana, the country’s tourism breadwinner or perhaps people assume the Caribbean’s biggest city is too busy for charm. Well, forget all that and come explore Santo Domingo’s colonial zone, stroll the seaside promenade, catch a baseball game, dance the merengue in a corner bar, and you’ll see why we have a little crush on the capital of the Dominican Republic.


Airbnb Santo Domingo

colonial zone airbnbWe did a four-day Airbnb in a local neighborhood in the colonial zone, a few blocks from the historic El Conde walking street and the ocean. How much? $18 with daily breakfast. It wasn’t anything fancy, but we loved our private room and rooftop terrace because it was in a real neighborhood with a lovely family. Chatting with our host Lilian and her sweet daughter Gabriela, getting recommendations for all the local eats (adored the empanada place on our street), and taking in life in the barrio was perfect. Check out that cute welcome gift of candies and hand-drawn picture Gabriela made us. What hotel does that?


Malecon Coastline

Malecon Santo DomingoArriving on a Saturday night, we dropped our bags and hit the town. Lilian recommended we check out the Malecon/seaside promenade and it was fun for the whole family. (As in, parents sipping rum and singing karaoke while kids drove battery-powered cars all over tarnation). Taking in the scene of boozy picnics and spontaneous dance parties along the water’s edge, we could tell this Caribbean coastline was going to be gorgeous by day. We returned in the morning for a walk along the palm-lined promenade and watched the waves crash on the dramatic limestone cliffs. (The only sad part was the floating trash. Santo Domingo, clean up your beautiful coast!)


Zona Colonial

Zona Colonial Santo DomingoWe zigzagged through the colonial streets, stopping at 15th-century churches and 16th-century plazas, culminating at Calle Las Damas, the New World’s first European-style street. Just off the river, Las Damas radiates to all the important monuments: The Panteon Nacional where the national heroes are buried, The Americas’ first cathedral, Ozama Fort (more on that later), and Plaza Espana with Alcazar de Colon—home to the Columbus family and now the Caribbean’s most important European art collection.


Ozama Fort

Ozama Fort Santo DomingoThe fort is worth a little wander. This sixteenth-century castle with nine-foot thick walls, was built by the Spanish to establish their dominance and protect the city from pirates and marauders. Captured by seven different nations and at one point imprisoning Columbus’ son and the country’s forefather Juan Pablo Duarte, this castle-turned-prison-turned-monument has stories to tell. Climb the tower to take in panoramic views of the city.


Museum Casa Reales

Casa Reales Museum Also on Calle Las Damas, the Casa Reales museum is a must-see stop. This 16th-century building and seat to the Spanish Colonial Empire, gives you a look into the beginnings of the New World with diverse exhibits and a fantastic free audio guide. As the “Gateway to the Caribbean,” Santo Domingo was the launchpad for all the great Spanish expeditions–Ponce de León’s colonization of Puerto Rico, Hernando Cortes’ conquest of Mexico, and Balboa’s journey to the Pacific Ocean. The museum traces the origins and impacts of these world-changing expeditions, plus the details of city life from the days when Columbus roamed the streets.


Ruinas de San Francisco

Ruinas de San Francisco concert seriesIf you can time a trip to Santo Domingo on a Sunday—do! Free concerts playing merengue, bachata, and salsa bring locals and travelers out for a massive dance party in the ruins of a 500-year old monastery. The quick rhythms bounce off the ancient structure, lit to perfection, and create an energy that keeps everyone moving. The packed dance floor spills over to the ancient stairs, walls, hillside…everywhere you look there are couples partner dancing. (That old guy in the yellow hat was working the floor like no other.) Pure magic.


Colmado After Party

colmados santo domingoWe left the concert after the band played their last number, but the music didn’t stop, it seemed to be coming from every direction. We followed the sounds of bongos, cowbells and laughter to Colmado Anthony. (Colmados are open-air corner stores with a few bar stools and a beer fridge so while people stop in for a loaf of bread, they can stay for a Cerveza Presidente.) A guy and soon-to-be friend, Jaime, motioned us over for a Cuba Libre and before you knew it, we were dancing merengue, sipping Mama Juana rum-wine, nibbling on freshly barbecued pork, and hanging out until close.


Dominican Big League Baseball

Baseball at Quisqueya StadiumJaime from the bar happened to be radio sportscaster so when we got taking about Dominican baseball, we convinced him to join us for a game. After the craziest series of shared taxis (no joke, speeding up the wrong side of the street to beat traffic), we arrived at Quisqueya Stadium to watch the Tigres de Licey play the Gigantes de San Francisco– one of the farm teams for the U.S. San Francisco Giants. We met one of the scouts from SF and there were about 10 other American there with radar guns clocking every pitch. The players were truly incredible and the game was so fast-paced and fun to watch. We had a blast (and so did everyone else drinking the bottles of rum they sell like soda pop), especially with Jaime giving us the inside scoop on the teams, stats, and gossip.


Los Tres Ojos National Park

Tres Ojos National ParkOur last morning in the city, we headed to Santo Domingo Este to see Los Tres Ojos National Park. Christopher Columbus’ remains are buried at the lighthouse here, but the real attraction is the series of open-roof caverns and underground lakes: Los Tres Ojos. Descending into these limestone sinkholes is straight out of Jurassic Park, between its jungly vines and teeth-like stalagmites. Explore the three teal lakes and pony up the extra 50 cents for the boat to the hidden lagoon.


Santo Domingo SLIDESHOW
“Oldest City in the Americas” SLIDESHOW


Santo Domingo had us moving to a new Latin rhythm and Caribbean beat. We just came from the Bahamas and have spent six months across South and Central America…and the DR already felt like the most vibrant amazing blend. The city is pulsing with culture and history, and gives the best context for the history of the Americas and this under-appreciated country. If the beaches and resorts of the Dominican Republic lure you in, make sure you fold in a few days for this surprising gem of a city, Santo Domingo!

2 thoughts on “The Oldest City in the Americas

  • December 14, 2015 at 10:31 am

    I enjoyed reading this. I’ve been to Punta Cana and La Romana (beach vacations) but it’s nice to read about the history and culture of Santo Domingo. I will have to make a stop there next time!

    • December 14, 2015 at 2:32 pm

      It’s a fascinating city that somehow seems to get bypassed on the way to the beach and back. Happy to hear you’ll be checking out Santo Domingo!


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