The Aristocrates of Caribbean Cruising
by 
Guy Matthews

Social relationships throughout time are acknowledged to exist on many concurrent levels with what can sometimes be perceived to contain hints of royalty and a touch of pariah among each and every level. The Caribbean cruising community, composing only one of many self-contained island social groups, is no different in its structure.  This community is populated by the committed sailor and is not limited to a single island, but encompasses the entire eastern Caribbean Sea. Arguably the Brahmins of the Caribbean cruising community are the couples who, after sailing the family boat to the islands, have spurned the conveniences of modern mainland life and discovered that what really matters in their life is the actual living of life without regret.  These wandering cruisers –the so called aristocrats of the Caribbean cruising life - who judge life and accomplishments not by the cost but by the value - are no longer possessed by the pursuit of even more and are not seduced by modern mega greed so prevalent in the mainland society.

There is a definite pecking order among the Caribbean cruising community where one’s status is judged not so much by material possessions as by the success and style of one’s lifestyle.  It is a community in which there is little discrimination between the haves and have nots and where vanity always comes in second to substance or quality.   Some well-heeled cruisers search out marinas with all available luxuries and conveniences, while the shoestring cruiser is content to remain at anchor, expending a minimum of resources for the luxuries associated with the good life.  Air conditioning, ice and similar comforts of modern society are seldom a part of the shoestring cruisers’ life style.

The lower echelons of this unique nautical social group, as defined by the chosen, include the bareboaters who are often the most affluent of the species and always gainfully employed, exhibiting the badges of a committed working lifestyle neither found nor desired by the Caribbean cruiser.  Large gold watches, new boat shoes, cell phones, neat shirts with little emblems on the pockets, and a willingness to spread money willy nilly throughout the watering holes of the Caribbean identify the bareboater.  The bareboater has not forsaken the pursuit of wealth and is in tune with tax reform, 401 K’s daily reading of the Wall Street Journal and other symbols of modern urban living. This individual has not paid his dues by making the difficult trip from the mainland by cruising sailboat. The bareboater arrives by jet airplane and gets onboard the professionally prepared cruising sailboat for a two week cruise, without having to worry about provisioning, charts, laundry, ice, engine operation, or any one of the thousands of hassles faced each day by the Caribbean cruiser.

The only social class below the bareboater is the cruise ship day tripper seen in some of the larger harbors in the island chain and known for causing an increase in taxi cab rates while the cruise ship is in port, and possessing a willingness to spend without regard to value or need – actions which cause the Caribbean cruiser to expend more to maintain their ongoing existence. 

The beknighted – the aristocrats of Caribbean cruising community – are known much by their boat name – “‘Tropic Moon’ is coming to dinner tonight,” as by their Christian names, and willingly and cheerfully face problems of daily living that would challenge any ghetto resident in the worst part of Kosovo. All of the many obstacles of daily living seem insignificant after the trip to windward on a cruising sailboat from the mainland, which involved the unrelenting east winds, moments of terror, physical exhaustion and daily life management challenges which would tax any Wharton MBA. Mates who have demonstrated an elegant sense of the style in past lives by such acts as complaining about first class service on Singapore Airlines, and who once regularly shopped at Neiman Marcus and Harrods, can, once in the islands, and inducted into the Caribbean cruiser class, become positively elated about access to a K-Mart and ecstatic by the possibility of fresh vegetables in a island grocery kiosk.

There are, of course, several sub classes of Caribbean cruiser that fall between the two extremes. Only the owner / crew of the crewed cruising charter sailboat are positioned above that of the aristocrats – a position achieved by their masochistic willingness to suffer more indignity at the hands of their paying charter guests in order to stay in the islands and maintain their cruising lifestyle.

The cruiser crowd can be further sub-divided into two general groups -those with a pet or pets onboard, and the petless that exist without any onboard domesticated animal.  While neither group can fully understand the motivation of the other, each group tolerates the other with only limited reservations.  Although dogs of all sizes and description are the most popular pet found onboard the Caribbean cruising boat, cats, birds, and even iguanas, are sometimes known to accompany the cruiser during island travels. Many of the dog owners profess that a barking dog is better protection from marauders than an assault rifle. The keen observator has also noted that there is sometimes  a inverse correlation between the size of the boat and the size and quantity of  pets found on the pet owners boat---  the  smaller that  the boat is, greater is  the likelihood that   the dogs  found onboard will be larger  or more  numerous than  found on the larger boat.    

The Caribbean cruiser is migratory with voyage choices dictated by the plan to find a safe haven for the boat during the hurricane season, with the assumption that if the boat is safe, the crew will be safe.  Many opt to take the boat to a harbor below 12 degrees north, which is considered to be mostly out of the paths of hurricanes.  The cruiser more inclined to take risks might remain in the Antilles with a plan to seek refuge in one of the many mangrove jungles in the event of an approaching storm.  There is a strong social element in the hurricane planning. There are as many types of multi-boat social events during hurricane season in the various hurricane harbors as there are Carnival activities in Trinidad in February.  

The threshold for initiation into the Caribbean cruiser class commences somewhere east of an imaginary line drawn between Georgetown, Bahamas, and Marina Hemmingway, Cuba. Trafficking with the cruising sailboat to the west of this line is that of coastal cruising and involves a more easily revocable commitment to the cruising lifestyle than that required by the cruiser who finally reaches Puerto Rico.  More than one cruiser’s life goal is known to have changed while transiting the area between the line of demarcation and landfall on Puerto Rican mountains.  It is a hard trip.

The aristocrats generally travel throughout the island chain in groups of twos or threes and communicate by VHF, single sideband or amateur radio in what seems to the uninitiated as a private pathos sometimes known only to themselves. Their social life includes a heavy diet of boat maintenance, shopping, toting ice, daily provisioning, reading, covered dish suppers, book exchanges, cocktails in the cockpit, cocktails on the beach, cocktails on the dock, daily radio nets, dinghy rides, sundowners and a variety of activities in and under the water.  Difficulties and pleasures are shared, and if one of the boats has a problem – mechanical, personal or social – there are many co-cruisers willing to come forth and help correct the problem.

Many of the aristocrat wives are second wives with the original now divorced first wife enjoying the shore side luxury of the old family homestead and a sizable chunk of the once joint possessions. The second wife, virtually always younger than the husband and sometimes barely older that the husband’s progeny, has to work harder, but has less of a vote in the Caribbean adventure. It is said that the second wife always carries groceries and ice down the dock, while the first wife worries only about freshness of the bread—a true indication that seniority and durability count on the cruising sailboat.

The toughness of the aristocrat cruiser wife can be attested to by the fact that while you can easily both impress and fool the second wife who has never seen a state capitol or a sunset at sea, it takes more than trinkets, travel and sea stories to impress or fool the wise old gal who has been around the circuit and married to the same old cruiser captain forever.

The names found on the transoms of vessels in the Caribbean cruising fleet often indicate much about the cruiser persona. The well read cruiser class mostly selects names that reflect their sometimes eccentric intellectuality or upbeat outlook on life, thus giving obscure Greek or Roman gods or hopes of serenity or escape a decided edge in the name game over some of the clearly thoughtless or embarrassing names found on some boats in the mainland fleet.  

An unspoken emotion that runs through the subconscious of most of today’s Caribbean cruisers is the worry that with the affluence of the modern world and development that is considered by many as progress, the cruising lifestyle of the islands will disappear much as the buffalo did when the west was tamed.  Accordingly, the astute cruiser species endeavors to enjoy the world as it is now and hopes that progress will not overtake common sense.  Most Caribbean cruisers experiencing a sort of geriatric adolescent hood know that life is a delicate balance of time, experience and seized opportunity and vow not to let it escape.