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.

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.
Regulations
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.
Ashore
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
Facilities
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.
Reading
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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