Is it just the 2 of you?...my guess is you seem kind of young to be taking on such a vacation..especially one that involves that much travel santiago to santo domingo..even if it is just one road basically....make sure its day light when you travel... many times we came up on area that the night before had been blocked by mobs, with trees and rubbish, and burned tires blocking the road.......not a situation that a young pair of kids would like to get involved in..Mostly the crowds are mad at the goverment for cutting the power or cutting off the water, or not fixing the roads...but there only needs to be a few real bad apples in that crowd to cause you lots of trouble...especially if you are white...at that age I would suggest one or the other and just stay local to that area. Neither place would be a beach-resort hot spot....but each person has their own view of a good vacation. Hopefully the tours use their heads as well. If you go out at night in Santiago take a trip to the monument on a friday or sat night especially if its nice out...the driveway up to the monument get packed with cars and music is blasting all over, and the view is decent.. I have only been through and into Santo Domingo at night...so cant help you there. have fun....bob