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I'm considering making a trip to a couple of these cities within the next year, and would appreciate some comparisons in terms of vibrancy, walkability, how "big" each city feels, architecture, cultural differences, and whatever else anyone would like to add. Also, how do they stack up against similarly sized South American metros (Medellin and Cali in Colombia, Salvador in Brazil) which I'm also considering a visit to. Thanks!
I'm also interested to know how the three Spanish caribbean capitals stack up. i've only been to Havana, but I've read a lot about the others and seen pictures of them.
I think Old Havana has the more colonial architecture and more fortifications than Old san juan and colonial santo domingo, However they are much better preserved in san juan. Havana is crumbling in many pants.
the infrastructure in Havana is in terrible condition compared to the others... I believe San Juan and Santo Domingo both have metro systems and both has more modern architecture.
culturally they are very similar. expect to hear reggaeton and salsa at all hours of the day. (and Merengue in Santo Domingo).
personally I think south america is more culturally exciting.
The largest of the three is Santo Domingo (in population and I think in population density too, landwise San Juan is the largest.) In terms of feeling 'big,' well Santo Domingo and San Juan have the traffic jams, etc of a major modern city. If by 'big' you mean having lots of monumental buildings, then Havana takes the cake.
Walkability falls on San Juan for the sole purpose that it has the best sidewalk infrastructure of the three. With that said, Havana is built along a more European urban model (Spanish to be exact while in the outer areas it takes more of an American urban prototype), and that means in terms of street grid and getting around on foot its the best suited. Santo Domingo is hit or miss, the Colonial Zone is very walkable though.
Architecture is practically the same in all three cities. Havana has more elegant buildings due to the time period when it was a wealthy city. Santo Domingo and San Juan are much more bland, mostly modern architecture based from Spanish styles.
Culturally they aren't that different. Havana people are better educated than in the other two, while in San Juan the average person is much more Americanized than in the other two. Santo Domingo is a mix bag. The reality is that once you visit one city, if later on you decide to visit any of the other two (or both) you will find youself at times believing that you are in any of the three cities. Obviously something will happen (you notice a flag, etc) that puts your feet on the actual soil you are walking on, but many urban streets in all three cities look very similar. The way the people behave is not that different either.
Medellin has a much more organized urban infrastructure than any of the three Spanish Caribbean capitals. I really think there's not much comparison there. Can't say anything about Cali, I don't know that place too well. In the rest of Latin America the cities where the ways of the people (and even in the architecture in many areas) resembles the Spanish Caribbean capitals tends to be in Venezuela, some cities along the Caribbean coast of Colombia, and Panama City in Panama. I personally think Panama as a whole, not just its capital city, has more affinity with the Spanish Caribbean than it does with the rest of Central America.
Personally, the area that I liked most of San Juan was Old San Juan. Unfortunately I don't think any buses or trains go there so if you don't have a car you might have to walk a bit to get there. I wasn't all that impressed with Condado. Condado just didn't impress me like other wealthy urban neighborhoods in Latin America like San Isidro or Miraflores in Lima, or Piantini in Santo Domingo. Avenida Ashford is the main strip but you just don't see crowds of shoppers or anything like that in other major cities.
There is an interesting Dominican neighborhood though centered on Avenida Borinquen in Santurce though.
There is a lot of sprawl in Santo Domingo but it was very modern. Piantini is a wealthy neighborhood where you have I believe two major shopping malls, Acropolis and I think you have Blue Mall in the area. You also have Agora, which I believe is another upscale mall.
It seems that wealthier people in Santo Domingo shop in these malls, while more working class people shop in those commercial streets. I wish I had gotten to see these for a more authentic experience.
Zona Colonial is nice. I believe the church where Columbus is said to have been buried is there. You do see tourists from Europe, Mexico, etc. It is closed off to traffic and is a pedestrian mall. I loved it. You do have a run down area nearby. A Dominican friend told me even nice areas where not too far from run down areas in the Dominican Republic.
Personally, the area that I liked most of San Juan was Old San Juan. Unfortunately I don't think any buses or trains go there so if you don't have a car you might have to walk a bit to get there. I wasn't all that impressed with Condado. Condado just didn't impress me like other wealthy urban neighborhoods in Latin America like San Isidro or Miraflores in Lima, or Piantini in Santo Domingo. Avenida Ashford is the main strip but you just don't see crowds of shoppers or anything like that in other major cities.
There is an interesting Dominican neighborhood though centered on Avenida Borinquen in Santurce though.
There is a lot of sprawl in Santo Domingo but it was very modern. Piantini is a wealthy neighborhood where you have I believe two major shopping malls, Acropolis and I think you have Blue Mall in the area. You also have Agora, which I believe is another upscale mall.
It seems that wealthier people in Santo Domingo shop in these malls, while more working class people shop in those commercial streets. I wish I had gotten to see these for a more authentic experience.
Zona Colonial is nice. I believe the church where Columbus is said to have been buried is there. You do see tourists from Europe, Mexico, etc. It is closed off to traffic and is a pedestrian mall. I loved it. You do have a run down area nearby. A Dominican friend told me even nice areas where not too far from run down areas in the Dominican Republic.
Don't know about Havana. Never been there.
I enjoyed my time in Condado/Carolina area. Took a evening trip to Old San Juan. Ponce and Vieques are on my go to's as well as Cuba. Not interested in the DR.
First off, thanks for this thread and for bringing these three Island Capitals to the fore.
One of my daughters was in La Habana in July; not for pleasure but for work. She was there 4 days. Her experience - while limited - was nonetheless wholesome and fulfilling.
She described the delapidated condition of most buildings surrounding her Habana AB&B. Yet, according to my daughter, the joy and friendliness of the Habaner@s made up for any and all aesthetic deficiencies.
El Viejo San Juan is a Jewel. It's beautiful, walkable, and well preserved. The locals are friendly, welcoming and helpful. This I can state from experience.
There's no reason to seek public transportation here. Everything is within a short walk. You will see Police presence, but not to an extreme.
Santo Domingo I've yet to explore. But it's on my destinations list.
I'm considering making a trip to a couple of these cities within the next year, and would appreciate some comparisons in terms of vibrancy, walkability, how "big" each city feels, architecture, cultural differences, and whatever else anyone would like to add. Also, how do they stack up against similarly sized South American metros (Medellin and Cali in Colombia, Salvador in Brazil) which I'm also considering a visit to. Thanks!
My vote would be for Havana, Vieques, Ponce as a destination. I won't speak on the DR, hopefully others can chime in.
First off, thanks for this thread and for bringing these three Island Capitals to the fore.
One of my daughters was in La Habana in July; not for pleasure but for work. She was there 4 days. Her experience - while limited - was nonetheless wholesome and fulfilling.
She described the delapidated condition of most buildings surrounding her Habana AB&B. Yet, according to my daughter, the joy and friendliness of the Habaner@s made up for any and all aesthetic deficiencies.
El Viejo San Juan is a Jewel. It's beautiful, walkable, and well preserved. The locals are friendly, welcoming and helpful. This I can state from experience.
There's no reason to seek public transportation here. Everything is within a short walk. You will see Police presence, but not to an extreme.
Santo Domingo I've yet to explore. But it's on my destinations list.
If you do go to Santo Domingo, you should pop in at La Barrica on avenida Lincoln. Its a very popular and large restaurant/bar with a very cool theme and architecture design, not to mention good food. Its actually part of a chain with several locations elsewhere in the city, but the one on avenida Lincoln is the most central and closest to the tourist spots.
What surprised me the most was when I learn that the owner is a Puerto Rican. He basically has a foot in PR and a foot in DR, feels at home in both places and is constantly going back and forth. The first time he went to DR it was against his wishes but had to due to a business reason. Once he step foot he was hooked. lol
Here's a quick presentation (in Spanish though) of this place and the other locations.
I love it when people from the Spanish Caribbean build businesses in those islands and create much needed jobs.
Anyway, Puerto Ricans seem to be doing quite well in DR. Many own successful businesses.
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