Having lived in Luperon on my sailboat and traveled around some of the island by bus and car - there are a few things you need to know about the D.R. It is an island of poor people and wealthy people and very little in between. The citizens of the D.R. are proud and basically very honest and friendly. However, as Frank V describes in the beginning of his guide the annual wages of the people and the
government officials is a pittance of what more modern countries earn. So there is a lot of "revenue/wage augmentation" practiced by the locals and officials whenever a cruising boat enters their waters. I must say they elevated it to an art form. Generally the amounts are small but some officials really push it up to some serious
money. And they have the
guns so you cannot argue with them even if you could speak their Spanish language.
It is illegal in the D.R. to leave any port without a dispachio and coastal cruising is forbidden. You must travel non-stop from your declared departure port to the next declared port and will encounter anywhere from minor to excessive
fees when you arrive at the next port. The whole fee thing is highly variable and up to the whims of the local officials.
So you must sail from one transient/tourist marina to another or one recognized port of entry to another port of entry. Stopping in between is not
legal but is done by some people and you can expect to pay heavily to locals who wear civilian clothes and claim to be Commandantes or some other form of official all of whom need to be adequately paid off by you before you can
anchor and depart for the next port.
Along the north coast there are very few
ports for cruisers and even less
marinas. Actually, Ocean World just west of Puerto Plata is the only operating transient marina on the north coast. Luperon has one very small marina, Puerto Blanco but it rarely has space and very ramshackle. Samana on the north eastern coast has no marrinas but is a fabulous stopover. The national park just southwest of Samana - "Los Haitses - is raved about by all who have visited.
Despite the absolutely wonderful topography of the island and the fabulous friendliness of the people, the officials are not interested in cruising boats beyond what they can extract from them in
fees and bribes. Having lived there I have no problem with this because without such "extra charges/fees" the official and his
family would be in a bad way.
If you are a North American cruiser out on your first
passage down island, you will usually be severely put out and pissed off at their "normal way of doing things." Europeans and others who have been exposed to this way of doing business in a poor countries have a much more enjoyable experience. But make no
mistakes this is an alien way of life to North Americans and takes some getting used to.
Whether you go south around Hispaniola or stay along the north coast you will be fighting winds and ways - you are in the Tropics and the
Trade winds blow east to west basically forever. The south coast has less of a westward
current but the winds are pretty much the same. From the
Bahamas you will be traveling south west then east to get around the south side whereas on the north coast you
head south to the coast of the D.R. then track east to Samana or the Mona
Passage.
Circumnavigation of Haitis is a "crap shoot". if your timing is correct you wil zip on around. But it you encounted Haitian boats filled with hundreds (really) trying to flee
Haiti to the Bahamas and on to the
USA - you probably will not survive the encounter.
IMHO unless you are coming from Central America/ Caymans/
Jamaica the south coast holds no advantages.
Regardless of taking the north coast or the south coast, once you get to the Mona Passage you will be bashing and crashing eastward directly in to the
trade winds and significant seas and waves until you get to the Spanish Virgins/USVI, and east.
Having done the passage a dozen times in nine years, I have found that if you are willing to wait for a rare great
weather window - which can happen tomorrow or next month you can have very benign and a pleasant crossing of the Mona. But the south coast of
Puerto Rico is not picnic. Usually you up anchor at sunrise and can make 20 40 nm east before 9AM or 10AM when the normal trades howl again and the seas build to 6ft to 8 feet or more. There are 5 different places wonderfully spaced along the P.R. south coast to duck into each day and wait for the next morning.
You will be
motor sailing the whole way if you wish to get anywhere before the "next coming". If you have a serious ocean sailboat you can sail but you will tacking between headings to to
South America and
Iceland. Again there are rare occurrences of really nice low winds and seas but don't bet on it unless you are willing to wait possibly a significant amount of time.
The
Dominican Republic is not the
USA or
Canada or even the Bahamas, it is a unique country and for first timers a good lesson of life in poor 3rd world countries. It is well worth the trouble and hassles - if - you have an open mind and sense of tolerance and humility.