Having spent the last 11 years in the Virgin Islands and Eastern Caribbean running charters aboard my Lagoon 410, Guiding Light, I have heard many sailors talk about going to the Dominican Republic on their way to the islands.
The problem is that once you start talking to them about the DR, they tell you they either spent the hurricane season in Luperon on the north coast or they used the DR to get to the southern coast of Puerto Rico to continue east to the islands. So few of them actually spent time cruising the DR to get to know it and its people. This is a shame because, while there are issues cruising the DR, there are also three great cruising grounds to explore.
The Southeastern Corner
When Lily and I cruised the Dominican Republic, we started in the southeastern corner of the country because we sailed over from Puerto Rico and checked into the country at Casa de Campo. This high-end marina is a great place to check in because the officials will meet you at the dock and escort you to the office. We had to complete paperwork for customs, immigration, health, sanitation, and more. It seemed like each person asked for $20 USD for their part of the process. The total we paid to check into the country was around $120 USD.
By the time we were done, it was later in the afternoon, and the marina, rather rudely, told us they did not have room and we had to leave. The problem is that in order to leave a bay, you have to get a despacho stating where you are headed, and I had not yet decided. The official recommended Bayahibe, and boy, was he right on target. This little, touristy, beachside town was a wonderful first look at the DR. While it took a bit to find a place to anchor amid all the local day boats, once we did, the island vibe overtook us. The first order of business at any new harbor is to turn in the despacho to the armada, but after that, you are free to explore all you want. We loved walking the beach and around town. We even ate at a fun restaurant called Gringos, much to the amusement of my Mexican girlfriend.