Rod Heikell's very informal site on sailing around bits of the world and an eclectic collection of things nautical or nearly so.

Sailing the Caribbean

A page of general info on sailing the Caribbean from the Skylax blog, old articles and new musings.

UNDER CONSTRUCTION...reorganising the World Sailing Pages



'Crossing an ocean in a small yacht is a bit like living your life backwards. At the beginning you die, then you get fitter and younger, and then when you arrive you have an orgasmic celebration and the idea that life is just beginning.'

Douglas Graeme

The other Caribbean: the Greater Antilles

The Other Caribbean

This is an info box from the forthcoming 2nd edition of Ocean Passages & Landfalls. See Imray for details (it should be out at the beginning of 2010)

Greater Antilles

The Greater Antilles comprising the island chain from Cuba to Puerto Rico is the lesser known Caribbean. For most people this is an insurance black hole and normal premiums for the Caribbean exclude Cuba, Haiti and the Dominican Republic. If you ignore the lack of insurance or pay an additional premium and disregard a lot of the stories that circulate about piracy and other goings on then this is a wonderful and largely uncrowded cruising area that is like stepping back into the Caribbean of 50 years ago.

Cuba is a huge island some 700 miles long with more than 2000 miles of coastline. It has a fascinating history and a vibrant culture that few fail to be enchanted with whatever you think of its folk-communism and the last days of Castro. It is surrounded by coral reefs extending up to 50 miles off the coast on the south side and it is largely untrammelled by cruising boats. Marina Hemingway near Havana is the only place you will see any real concentration of yachts and many of them don’t go anywhere else. Around the south side I saw fewer than a dozen yachts sailing around in a six week cruise.

Jamaica is one of the most beautiful islands in the Caribbean, but is a troubled place with a lot of violence away from places like the gated holiday compounds in Montego Bay. There are a number of good anchorages around the island, but you are probably best going to Port Antonio, Montego Bay or the Royal Jamaica Yacht Club in Kingston.

Fishing boats in Ile a Vache

Haiti is a difficult one to pick and although I have cruised there without incident, other yachts have come to grief. You need to pick just one or two spots to go to that are safe and leave the rest. On the north coast most yachts will put into Cap Haitien. On the south coast Ile a Vache is the best destination and here a French couple run a small ‘hotel’ and have moorings with a guard. You need to carefully judge the political situation there and determine whether things are relatively settled, at least as settled as they get in Haiti, or whether it’s best to give the country a miss. If you do go there it’s a bit like stepping back 50 years with fishing boats working under sail alone and dug-out canoes all over the place.

The Dominican Republic has a limited number of marinas around the coast and recent developments have tended to be marina/apartment complexes. Luperon and Puerto Plata on the north coast are popular stops while on the south coast there are a couple of small marinas with berths and a few deserted anchorages.

Puerto Rico has the most developed infrastructure for yachts with marinas concentrated around the eastern end of the island, though there are anchorages and small marinas scattered around the other coasts of the island. It also has the island group off the eastern end known to cruisers as the Spanish Virgins and there are some wonderful anchorages around the group that are just as beautiful as any around the US and British Virgins but without the crowds.

Sailing strategies

Yachts will be on three general tracks: coming north from Panama and Central America, south and east from the USA, or west from the Lesser Antilles.

  • From Panama yachts will have a hard time getting north against the northeasterly trades until at least around 15ºN when the trades start to get a more easterly component (see CAR3).
  • From the Lesser Antilles it is an easy downwind run along the Greater Antilles and the only real choice will be whether to go north or south of the Greater Antilles. If you are interested in cruising this area it is best to go south of the islands and then make a decision on whether to go north or south of Cuba. Going south of Cuba would be my favoured option leaving it late in the winter season to round the western end of Cuba when the trades are a lot lighter.
  • From Florida the commonly used route via the Bahamas (CAR5) touches on the northern coasts of Dominican Republic and Puerto Rico, but for an extended cruise in the Greater Antilles I have crossed to Marina Hemingway and then cruised east along the southern side of the island chain. It is not always easy against the prevailing easterly trades, but you are helped at times by fronts passing to the north which will disrupt the trades. At times there are also land breezes off the large islands which effectively ‘hold-up’ the trades so there is less wind and there can be a northeast or even northerly breeze at night on the southern side of the islands.

Seasons and winds

The Greater Antilles lie in the North Atlantic hurricane belt and so the seasons are effectively the same as anywhere else in the Caribbean: yachts cruise in the winter months from December to May and move out of the area in the summer from June to November. Hurricanes regularly hit the Greater Antilles when they start curving NW up towards Florida and in recent years with increased hurricane activity there has been much damage, especially in Haiti, Jamaica and Cuba.

In the winter the prevailing winds are easterly along the southern side of the island chain and east-northeast along the northern side. The trades blow anything from 15-25 knots and push fairly big seas along the northern and southern sides of the islands. In the channels in between the islands, especially Windward Passage between Cuba and Haiti and the Mona Passage between the Dominican Republic and Puerto Rico, the northeast trades are accelerated and these can be very windy places indeed.

In the winter months with the brisk trades temperatures are in the mid-20’s to 30ºC range and the humidity is not excessive. In the summer it is hotter but it is really the higher humidity which makes life less pleasant.


Puerto Rico   You need a US visa BEFORE entry if you do not have a US passport. Clear in at the first customs area where you can get a cruising permit valid for a year. Immigration will stamp your passport. Upon leaving telephone customs and post the immigration docket back.

Dominican Republic   You must clear in and out of every port where there are customs and immigration. A tourist visa is issued for 60 days. Small ‘gifts’ are appreciated.

Haiti   Clear in at Cap Haitien where there are customs and immigration. Things are ‘looser’ at Ile a Vache. Small gifts are almost mandatory though large gifts will be requested.

Jamaica   Clear in at Montego Bay, Port Antonio or Kingston where there are police and customs. A small gift is often requested and worth paying.

Cuba   You must clear in at a major port with a marina with Marina Hemingway near Havana, Santiago in the southeast and Cayo Lago on the south coast the most popular. Yachts must submit an itinerary and check in and out of ports with any officials. Checking out of Cuba must again be from a port with a marina. Despite the cumbersome paperwork it is well worth cruising the island. Small gifts will often be asked for.


Puerto Rico   Good American style supermarkets and a wide choice of restaurants and bars.

Dominican Republic   Reasonable shopping and a good choice of restaurants and bars at reasonable prices.

Haiti   Little in the way of restaurants and bars and don’t bargain on finding anything in the way of provisions though there are some interesting local markets.

Jamaica   Some good restaurants and bars though you need to be careful of where you drink at night. Mediocre shopping for provisions.

Cuba   You will find small simple restaurants and cafes serving simple meals depending on availability, but don’t come to Cuba for the food. There are also official and semi-official paladars where you eat in someone’s home and where the food is generally better. Bars are excellent and so is the rum. Shopping in Cuba is poor because of the American embargo and you should not bargain on finding anything more than the basics and some fruit and vege.


Port Antonio on Jamaica


Yacht facilities are limited until you get to Puerto Rico and the marinas and yards on the eastern end of the island. The exceptions are Port Antonio in Jamaica and some developing facilities around the Dominican Republic. Elsewhere you will have to fend for yourself and in places you will need to ferry fuel by jerry can.


The Gentleman’s Guide to Passages South   Bruce Van Sant. Cruising Guide Publications. Recommended.

ICH chart kits. Seven A3 size chart books covering the coast of Cuba published by the Cuban Hydrography Office (ICH) and available in Cuba. Essential for cruising Cuba’s coast.

Cuba: A Cruising Guide   Nigel Calder. Imray

Cruising Guide Puerto Rico and Spanish Virgin Islands   Steve Pavlidis. Seaworthy Publications.

Puerto Rico, the Spanish, U.S. and British Virgin Islands (Street's Cruising Guide to the Eastern Caribbean)   D M Street. iUniverse.


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