10 Reasons Why Santo Domingo is the Coolest City in the Caribbean

santo domingo dominican republic calle jose reyes

I’ll start with this: Santo Domingo really surprised me. What was meant to be a quick stopover on my way to the tropical vibes of Punta Cana ended up being my favourite place in all of the Dominican Republic. This charming capital city is pretty much everything you’ve ever romanticised about a sleepy colonial town in the Caribbean. Old men gathered around a game of dominos slowly sipping on their rum, palm trees casting their shadows on the old wooden bench you’ve found to watch the world go by and crumbling walls so beautiful you forget they are, in fact, still crumbling.

I imagine Santo Domingo is what Cartagena, Colombia used to be, before the hordes of tourists arrived to steal its magic. A true colonial gem dripping in charm and character. Except no one seems to have taken much notice in Santo Domingo yet. So rather than finding yourself queueing up with loads of other tourists for that quintessential snap, you feel like you’ve almost got the town to yourself.

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Streets of Santo Domingo

Santo Domingo is small and walkable. So you can pretty much explore the city in a single day; two if you really want to slow travel. I spent nearly 36 hours in town and that was plenty for us to become fast friends. It’s a great city. So if you’re heading to the Dominican Republic, squeeze some time into your travel itinerary to enjoy this charming capital and get a real taste of Dominican life before switching off at your nearest beach.

Here’s how to make the most of a brief visit to Santo Domingo:

Santo Domingo: Where to Sleep

Base yourself in the Zona Colonial, the UNESCO-designated Old Town, so you can really make the most of a short stay. You’ll find plenty of affordable and chic accommodation right in the heart of town. We booked a great mid-range option, Villa Colonial. This former colonial home is now a cool artsy hotel where you can pretend to step back in time. Not to mention that the breakfast is superb.  

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Hotel pool and breakfast nook

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Hotel patio

If hostels are more your thing, Island Backpackers Hostel is the place for backpackers to see and been seen.

And if you’re all about that luxury, then book a stay at Hodelpa Nicolas de Ovando, a travel blogger favourite.   

Santo Domingo: Top 10 Things to Do

1. Start your day sampling a traditional Dominican coffee. It’s strong, tasty and will give you just the buzz you need to pound the pavement all day. The Dominican Republic has been on growing coffee since the early 1700s, so they certainly know what they’re doing. If you want something really local, head to your nearest corner shop and pick up a simple black coffee for under a £1. If you want something more Insta-worthy, then don’t miss Mamey Liberia Café. Regardless of where you end up, you won’t be disappointed in those rich flavours.

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Sampling Dominican coffee

2. Use your caffeine kick to hit up your first landmark – the beautiful Cathedral Santa Maria la Menor. Here’s a cool travel fact: this is the oldest church in the Americas. Back in good old 1492, you know, when Colombus sailed the ocean blue (anyone else remember that phrase from school?), he landed here and built this beauty, which quickly became the hub of Catholicism across the Americas. How cool is that? Historical cool, not like, colonialists conquering the world cool.

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Cathedral Santa Maria la Menor at the Golden Hour

3. Pop over to the Alcazar de Colon, the palace that was once home to Colombus’ son, Diego. It’s also where conquerers like Vasquez and Cortez used to chill and map out their plans for growing the Spanish Empire. And it just so happens to be what I think is the most beautiful building in town.

4. Go for a little break in the city’s main square, Parque Colon. In fact, find a bench, settle in and soak up local life. This really is the town hub and it’s busy pretty much any time of day. Plus, it’s the perfect spot to get some respite from that strong Caribbean sun. (Or in our case, afternoon thunderstorms.)

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Watching the world go by in Parque Colon

5. Head to Caoba Cigars and get a crash course in cigar-making. The Dominican Republic is one of the world’s top cigar producers. Which means you’re bound to stumble on a local factory where you can learn about the craft and, if you so desire, sample a cigar or two. We popped into Caoba, which is right off the main square, and spent most of the afternoon chatting to the staff and learning all things tobacco. There’s a room for each step of the process and you can watch the team in action, doing everything from cutting tobacco leaves and rolling up cigars to drying them out in the cellars and packaging them up for export. 

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Entrance to Caoba Cigars

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Smiling and holding my breathe at once in the cigar cellar

6. Walk through the city’s colourful streets at Golden Hour. Santo Domingo is quite possibly one of the most colourful cities I’ve ever been to. Don’t miss taking a stroll through some of the town’s residential roads to admire all the vibrant tones. Calle Jose Reyes is particularly popular so start there and work your way around the area.

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Posing with Santo Domingo's colourful streets

7. Grab dinner in a local spot and sample one of many delicious Dominican dishes. There’s Sancocho, a traditional meaty stew, and Mangu, smashed plantains that are typically served with fried eggs, salami and fried cheese. You also don’t want to miss out on delicious Tostones, toasted plantains that accompany any meal as well as the well-known sides of rice and beans. Indulge your sweet tooth with Dulce De Leche, a sweetened milk that tastes like caramel and literally melts in your mouth.

8. Walk off your food on the Malecon. If you time things right, you can head over to the promenade for a nice evening stroll. Here, you’ll mix with the locals as you take in the views along the water. This is a prime spot on Sundays.

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Charming Santo Domingo streets

9. Wake up early and head to the Mercado Modelo. This market will be a feast for your eyes and your belly. You can literally find anything here, from the local alcohol-infused delicacy, Mama Juana (a drink made of rum, red wine, honey and local herbs that’s said to be an aphrodisiac), to love potions to cure a broken heart to fresh vegetables in every colour of the rainbow. This is a great place to grab a street food-style breakfast and a strong coffee too.

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Bananas and pineapples, my favourites

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Rather large cinammon sticks

10. Bring home some Larimar, the famous Dominican gemstone. With so many local treats, it’s hard to choose just one souvenir from the Dominican Republic. But, if at this stage you still haven’t succumbed to a bottle of Mama Juana or some local coffee beans, then consider treating yourself to Larimar, a stunning stone that’s exclusive to the Dominican Republic. It was discovered in 1974 and is named after the explorer’s daughter (Larissa) and the sea (mar in Spanish) because of its baby blue hue. And it will remind you of the country’s beautiful waters every time you put it on. You can even make a visit to the Larimar Museum your final stop if you’re keen to learn more about this precious stone. 

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