Certainly spend some time in the city, there is nothing like this in the Caribbean.
Architecturally, you will not see a more varied and spontaneous architectural mish mash in any city in this archipelago as you will see in Santo Domingo. Architecture ranges from grandiose and historic colonial to the sublime and boring boxes.
Dining is an artform here, with such a choice! Whatever your mouth desires is almost certainly available, or at the very least, attempted to be satisfied by a great chef or cook in one of the many restaurants. In this category too, the quality of the restaurants ranges from worldclass to the "how on earth can people eat here" type of places.
Culturally, there is no better entrepot of culture in this country. Santiago comes a close second, but in pure number of cultural venues, Santo Domingo dominates this scene. From theater performances to a vibrant street scene, where a real clown enternating the pedestrians or an intense chess game in the Colonial Zone by young Dominicans, this city truly offers plenty and then some. Worldclass art (Dominican, international, and Haitian art abounds, - tip: don't buy Haitian art from the streets, much of it is pure mass produced garbage. If you want quality Haitian art, go to the many galleries. Also, Dominican art and international art of quality are available in the many galleries as well, some will even ship the precious item to your home, if you insist). Of course, this is not New York or London, so if you are thinking culture on those level, then think again. But, this is Santo Domingo and in this region of the world, this is as good as it gets in the culture department, and its pretty good.
Museums are plenty, from tiny museums detailing particular events that the city has been witness to impressive museum detailing everything of what it means to be a Dominican! Some museums are predictable, such as the Museum of Natural History and Geography with the usual things on the display as in many other such museums around the world and others are unique in the planet, such as the Viceregal Museum of the Columbus Palace or the Museum of the Royal Houses or perhaps, the Numismatic Museum where coins collected from historic Spanish galleons are on display and some are even on sale!
History? Well, let's see. The city has been in existence for over 500 years and thus, makes Santo Domingo older than Lisbon and this is a European city that we are comparing it too! So, yes, we got history here, plenty of it on the par excellence of new world firsts list!
Shopping, this is the spot. Get bargains in flea markets and indoor markets or at La Sirena store, perhaps you want some high swank? There are plenty of shopping malls to be strolled, from Plaza Central to Unicentro Plaza to a long list of other plazas offering items that are both globally available and unique at the same time. One would say that it would not be worth to buy something that's available in your home town here, but the truth is that buying a Tommy Hilfiger shirt at Plaza Central will always remember you of your Santo Domingo trip, whereas buying the same shirt in your hometown will not! Thus, buy things for the sake of memory enhancers, afterall that is the reason people travel, to make memories and new discoveries of the world!
There is plenty more on offer, so come with your mind ready to see Dominicana ala metropolis style! Of course, there will be some shocking things you will witness, some things you may not be used to. There are some very poor areas of town, then there are the really wealthy and the inbetweens. Plenty of luxury cars and plenty of people dependant on public transport. Orderly avenues with chaotic traffic. This is certainly a city of contrast, but so too is the Dominican spirit. In fact, diversity and contrast is what the DR is about from its geography to its people to its culture to its food to its developmental patterns.
To try to make sense of it all would be a monumental task, but just accept this country and this city for what it is, a place that cannot be easily defined as this or that, other than purely Dominican!
(BTW, I will suggest for you to stay overnight (2 days or so) in the city and check in at a hotel in the Colonial Zone. If you can afford it, try to stay at the Nicolas de Ovando Hotel, its in a palace of the governor of the same name in the Colonial Zone. The palace is around 500 years old, its the closest thing to traveling back in time, though you will see yourself traveling back and forth through time throught this country. Comfy luxury buses speeding along paved highways while the side show from the windows shows donkey trails and real donkeys from time to time.
The DR ranges from the 21st century to the 16th century and every century in between. Come and explore with open eyes and experience this interesting and perhaps, exciting kaledeoscope of the Caribbean.
-NAL