Winter Destinations: The Forgotten Caribbean


In this first installment of a multi-issue look at winter cruising destinations, we’re dropping anchor in three off-the-beaten-path spots in the Greater Antilles that are overlooked by most cruisers.


At anchor at Casa de Campo Resort in La Romana, Dominican Republic. © freecruisingguides.com


Black River, Jamaica
Many of us go cruising and say we do it because we want to explore new places and experience other cultures. However, if you watch cruising patterns, the majority of cruisers stick to the beaten track and for many that means not wandering too far from one’s own culture as well. Antigua, the Virgin Islands and Grenada have always been popular as “Caribbean destinations” because they are English speaking and until recently have been considered 100% safe.

An island like Jamaica has seen fewer cruising boats because some members of the yachting community read crime statistics arising from inner city Kingston, the capital, and extrapolate them to the entire island. As Caribbean islands go, I have found Jamaica to be as safe as the average. Some rank safer, and some rank worse. Everyone fears what we do not understand and it is easy to misunderstand Jamaica. Jamaica is an extraordinary country. A country of “wood and water,” of smiles and music. Jamaica is “the celebration of African Culture in the Caribbean.” Its music, art and culture have impacted the entire world.

The Black River, on the South Coast, is Jamaica’s longest river. The town of Black River is a nice town set on the river and today is active with eco-tourism. The river is famous for its birds – herons and snowy egrets, among many others – and for its crocodiles. There is a bridge over the mouth of the river which unfortunately does not allow for sailboats to go upriver. There is a dock at the mouth of the river that carries eight feet. More than that and you will have to anchor out and dinghy in. The Black River Bay is reasonably well protected and provides for good shelter and good holding. 

The Black River is so called because the waters are stained by tannins which make the river the color of molasses. There a series of falls on a private estate. They are probably the best
waterfalls in all of Jamaica and well worth your time and effort to
visit. The falls are set between limestone cliffs and surrounded by
forest. A dip in one of the eight pools is sheer joy. The waterfalls
are absolutely pristine. When you inquire about the river tours
just above the bridge, you can also ask about tours to the falls. It
is an easy trip and well worth it.

It is never easy to define culture, and Jamaican culture is no exception. In its simplest terms Jamaican culture incorporates Arawak native American, a diverse amount of African influence (diverse in the sense that Africa is a large continent and the African Jamaican population came from many different areas of Africa with distinctive traditions), as well as East Indian, Chinese and others who came to Jamaica over time. Plus 300 years of British rule whose impact does not go unnoticed in so many areas of Jamaican life. “Out of many, one people.” So it is that Jamaica developed.

Jamaica is strong in tradition. The famous Nine Night after a loved one dies is part of almost every Caribbean country, and in Jamaica to witness a Nine Night is something of an event that gives rise to the spirit. Surely it is one of the best cures for grief that I have ever witnessed.

Jamaicans have a tremendous sense of humor which peppers their conversation all the time. They constantly tease each other for whatever. A very warm and friendly people, they have a wonderful sense of hospitality. As in any relationship, it takes time for these traits to come through. Certainly street vendors have their own priorities, the biggest of which is to sell you something. It is important that you not take repeated advances personally. Remember to smile and say, “Little more time, mon, little more time.”

Vieques, Puerto Rico
Inasmuch as many cruising sailors define “The Caribbean” as the Lesser Antilles (Virgin Islands to Grenada), the Greater Antilles and thus Puerto Rico are often overlooked. This is indeed unfortunate as Puerto Rico is truly a wonderful and safe cruising ground, offering exceptional cruising on all of its coasts as well as superb opportunities to explore inland.

Puerto Rico is an island of the Caribbean and as a result is made up of and reflects Caribbean culture. That culture comprises Native American (Taino), African, European and a small amount of “other,” with a distinct patina of the culture of the United States which has been associated with the island since 1898.

Puerto Rican culture likes music and it likes color. It is not in a rush, and being in a rush is bad form in Puerto Rico. The culture is not utility-based like that of North Americans. Its values are based on “sentidos” and thus putting people’s feelings first is most important.

Puerto Ricans say “Buenos Dias” to each other in the morning. They nod to each other when they walk into a room, even if they do not know each other. They smile a great deal. If you were to visit a Puerto Rican with something in mind that you wanted to accomplish, it would be considered very bad form if you went directly to the subject. Keep this in mind when you anchor, or come into contact with the authorities who will clear you in, or when you enter a slip in a marina or perhaps even a store.

If you speak a little Spanish, so much the better. Many people have asked me if Spanish is a necessity in Puerto Rico. Actually, most Puerto Ricans are bilingual and many trilingual. As to their “English,” you will find most as fluent as residents of North America. However, most prefer Spanish or at least some Spanish mixed with English.

If you choose to anchor in Vieques (an island off Puerto Rico’s East Coast), the nicest beaches are located just to the north of Point Bermudes, which is about half way down the coast from Punta Arenas at the Northeast corner.

Remember, if you are coming from the east along the north coast of Vieques, to give the reef off the Northeast corner a very wide berth as it breaks in weather and in some spots there is insufficient depth. There is a great deal of rock on the bottom along the west coast, so you have to be sure to set your anchor. If a norther comes down, this is not the place to be as you will roll. Move to the south shore. You will find the area safe.

Esperanza is a pretty little place and spending time here is easy. The town has its share of restaurants and bars and you will have no trouble finding cruisers and locals alike to socialize with. The South Coast of Vieques is very much like the south coast of all the islands in the Greater Antilles during the early part (December through March) of the Trade Wind season. It offers more protection against strong Trade Winds and northers that come that way from North America.

There are a number of restaurants worthy of your consideration including those that are instantly recognizable by cruisers, as so many of us gather there. Duffy’s is the kind of place where you can simply relax, get a good meal and meet other cruisers as well as locals. Right next door to Duffy’s is the Vieques Conservation Historical Trust, which you may want to visit. They will give you free information on the island, much of its history, and what is being done to preserve it.

Bahía de las Águilas, Dominican Republic
The Dominican Republic is a beautiful country with numerous anchorages that are still virgin. They are well worth your time and expense to see. You will discover uncrowded anchorages; clear, clean water; breathtaking views; really wonderful people; and much more.

The Dominican Republic has three coasts: the north coast, the east coast and the south coast. The south coast of the Dominican Republic is the safest and more interesting coast, as it has so much more to offer than the north coast. This alternative makes for better and safer sailing as well as providing a host of beautiful harbors and anchorages.

Just five miles south of Cabo Rojo, you enter into the Bahía de las Águilas (Bay of Eagles). The bay is quite large. From the Northeast corner to the Southeast corner you will find great anchoring spots. I like to anchor in front of the “picnic building,” an observation tower in the Northeast corner. The bay is not connected to the mainland by any major roads, so you will not find hotels, stores or restaurants. What you will find is nature at its best. An abundance of wildlife. White sand beaches and crystal water. There is nothing at all to do, but walk on the beach, swim and dream.

If you do not like isolation, do not come to this anchorage as most times you will be the only boat, perhaps the only person, there. You will see a few fishermen on land and in their boats, and they may come over to offer you fish and lobster. The sunsets are in a class of their own.

The Bay of Eagles is one of those rare spots that are increasingly hard to find in today’s world. This is cruising the way it was when I first started sailing. You drop the hook and you are in a world of your own. And if another boat comes in, unless otherwise indicated, you keep your distance. Call it what you like, sailing etiquette or common sense; everyone likes their privacy. And here the one thing you can find for sure, is privacy.

Some things in the Dominican Republic are downright cheap. Petroleum is not! Fuel prices run about 30% higher than in the US, albeit you may find the price lower than in Europe. Propane gas, on the other hand, is comparatively less expensive as it is government subsidized. Since most homes use it for cooking, it’s available virtually everywhere.

Working for tips is a very big part of the Dominican culture. Sometimes cruising sailors complain about having to give a tip or refer to it as a request for a bribe. Getting one’s cielito or propinita (little treasure or small reward) is part and parcel of Dominican culture, and most Latin cultures in the Caribbean. Learn how to give a small gift graciously or how to smile and say no. Avoid being dismissive or rude if you are asked. Respect and courtesy is highly valued at all levels of Dominican Culture.

While no harbor anywhere in the world is 100% secure as to personal safety or theft, the Dominican Republic is in the top tier on the Caribbean list of safe places to cruise. If the Coast Guard (Marina de Guerra) comes out to visit you after you anchor, be sociable, since you will almost always find them to be so. They want to look out for you and they want your stay to be good; it’s their job. A small tip or gift when you meet them goes a long way to cement the relationship.

The Dominican Republic is part of a very large island. Take your time, as there is so much to see and to enjoy. The weather is normally excellent, the people friendly and the cost inexpensive to modest. Last but not least, let us not forget the nightlife. If you like nightlife and you like to dance, you will think you died and went to heaven. Meringue, bachata and salsa until your legs fall off! And if you do not know how to do it, look up and smile, and you will be swept off your feet.

The biggest problem in the Dominican Republic is easily summed up by a saying that is often used in the town of Nagua. “Entre si tú quieres, sal si tu puedes!” Enter if you want, leave if you can!

This article is excerpted from Frank Virgintino’s A Cruising Guide to the Dominican Republic, A Cruising Guide to Puerto Rico and A Cruising Guide to Jamaica, and is reprinted with permission. To read the guides in their entirety (as well as guides to the rest of the Caribbean), visit freecruisingguides.com.

Frank Virgintino is a native New Yorker who has spent over 20 years living and cruising in the Dominican Republic. His sailing background of over 40 years covers the Canadian Maritimes, all of the eastern seaboard of the United States and the entire Caribbean, many times over. Aside from cruising, he has spent the better part of his career designing and building marinas.

Be the first to comment

Please check your e-mail for a link to activate your account.






Click here to download WindCheck's November/December 2018 issue. (File is 5MB)


WindCheck October 2018

Click here to download WindCheck's October 2018 issue. (File is 5MB)