This is a wonderful dream trip for the futute.. Right now we are still dealing with open boats taking people to Puerto Rico and drug dealers on their way to Miami. East of Samana there can be really heavy water. There are some trips that go by boat from Punta Cana up to see the whales during the season.. (guess they just stop the yola and drug trafficing for high tourist season)... so if you are here then .. Jan thru March. and fancy a trip that would be one solution.
The other idea is to contact Luperon Marina .. which is the best hurricane hole on the north coast.. and ask them if they have any boats that take passengers.. Those are the guys whom I would think know the most about the waters.
But, wow, what a lovely day it will be when we no longer have to worry about refugees and drug dealers.
Listen, you can take the girl out of the sixties but you cannot take the sixties out of the girl
It is always possible to find somebody with a boat who will do anything for money. But traveling by boat is a bigger deal than someone not familiar with the waters might think.
I lived and cruised on a seaworthy 36' sailboat for 16 years, using Samana has my home port. I have made the trip between POP and Samana several times. It is a long trip and there are no safe harbors in between in case the conditions turn bad, you get seasick, or whatever. Itis a lee shore. Until almost to Samana you are in the Atlantic and from now through the winter the conditions are risky. As fronts cross the US, they usually drop down as far as the North coast giving us substandard weather and rough seas. For my wife and it took us from the late afternoon of one day to the morning of the next, travel at night generally recommended because the seas tend to be calmer.
To go to Punta Cana from POP, your first harbor is Samana. Cruising boats often wait days or even weeks for good conditions in the Mona Passage to make the crossing to Puerto Rico. To go from Samana to Punta Cana, you will follow the coast, most likely travel at night, and have no harbor to duck into. Conditions in the Mona Passage are very unpredictable and you will be traveling over extensive areas of shoals where the water depth changes from 6000 feet to shallow, causing rough conditions.
I am not trying to scare you, just reporting how it is. And it is because of my experience that I strongly recommend taking the bus unless you are experienced on the sea, absolutely sure you are immune form sea sickness, and have a very good boat. There are more reasons for this than refugees and drug dealers.
PS: If you get in trouble, there is no US Coast Guard boat to come to your rescue.