You'll find the routing quite direct and the seasonal timing you've chosen to be ideal. A side benefit is that, if the boat should give you some problems, you have several places to stop along the way: Samana near the DR's eastern end and Luperon, the yachtie favorite and protected estuary, just past Puerto Plata. There's also a protected anchorage among the shallows near Manzanillo. The downside of your route is where the Channel thins considerably, you must remain outside Cuban waters (which they monitor closely) and also deal with fairly dense shipping traffic. Be sure to think about your watchstanding routine on this segment of your run, doubly so if you are short- or single-handed.