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The Cayman Islands are the most upscale, safe and culturally diverse destination in the Caribbean, offering the greatest variety of activities, true world-class dining, tranquil crystal clear waters, white sand beaches and lavish accommodations; all rich in genuine culture, charm and hospitality. All of the establishments we recommend have been carefully selected after a diligent screening process to bring you only what we feel to be the very best of the Cayman Islands. We pride ourselves on introducing visitors to the most crowd-free and rewarding experiences imaginable, all with the very best savings and absolute highest value.
Spend a little time gathering knowledge about the Cayman Islands and arrive with enough information to ensure that your Cayman Islands vacation dollars return the highest value. A few hours of research will save you hundreds of dollars and take all the guess work out of your Cayman Islands vacation. Our readers spend 10-20% less than the average Cayman Islands visitor and achieve the ultimate Cayman Islands vacation experience, free of crowds and disappointment. It takes most visitors many trips to gain the knowledge that can be found right here on this site and our corresponding forums.
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On a 1585 voyage, Sir Francis Drake reported sighting “great serpents called caymens, large like lizards, which are edible.” A few years later a French map showed Cayman Brac with crocodiles in its waters, along with a manuscript describing the iguanas. In 1993 an archeological dig on Grand Cayman - and three years later on Cayman Brac -proved the existence of the crocodiles. However it was the turtle that continued to attract sailors to the Cayman Islands. For years, the Cayman Islands served only as a pit stop on these maritime runs.
In 1655 the Cayman Islands came under British control when Jamaica was captured from the Spanish by Oliver Cromwell’s army. Tucked near Jamaica and Spanish-ruled Cuba, the British believed the Cayman Islands to be a strategic location.
According to legend, some deserters from Cromwell’s army fled Jamaica with escaped slaves and arrived in Cayman Brac and Little Cayman in 1658. Allegedly, their names were Watler and Bodden, and today some of the Cayman Islands oldest families - the Watlers and the Boddens are their descendants.
The possession of the Cayman Islands by the British Empire would not become official until 1670, when the Cayman Islands were ceded to Britain along with Jamaica by the Treaty of Madrid. The British tried to settle the formerly uninhabited island of Grand Cayman but continuous problems with Spanish pirates sent the settlers back to Jamaica after only a year.
The population of the Cayman Islands slowly increased and the first royal land grant in Grand Cayman came in 1734, marking the first permanent settlement in the Cayman Islands. Through 1800, the Cayman Islands continued to grow in population with the arrival of shipwrecked mariners and Caribbean immigrants. Cayman Brac and Little Cayman remained primarily uninhabited although some records indicate the tiny islands were settled but later abandoned when residents were attacked by pirates
For years, the Cayman Islands served as a magnet for pirates and buccaneers such as Sir Henry Morgan, who enjoyed the tropical climate and remote location. During the American Revolution, American privateers challenged English shipping, aided by the war ships and merchant ships of France, Spain, and Holland. By 1782 pirating had become less prevalent and buccaneering drew to a close.
According to recent research, in 1794, a great maritime tragedy took place off the east end of Grand Cayman. The Wreck of the Ten Sails is still legendary in the Cayman Islands, recalling the tragedy of the Cordelia, which was part of a convoy of merchant ships. The Cordelia ran aground on the reefs at the east end of Grand Cayman and frantically sent a signal to the other ships in the convoy to warn them off the dangerous reef. Sadly, the signal was misunderstood and every ship in the convoy eventually ran aground on Grand Cayman's East End reef. East End residents were credited with their brave actions that saved many lives; an act that King George III later recognized. Various stories explain that the King granted the Cayman Islands freedom from conscription and other versions say that the king gave the Cayman Islands freedom from taxation. Whichever version you choose to believe, to this day the Cayman Islands remain tax free.
In 1832 the citizens of the Cayman Islands met at what is today the oldest remaining building on the island - Pedro St. James Castle. Known as the “Birthplace of Democracy” in the Cayman Islands, this historic site witnessed the first vote, which created the Cayman Islands first legislature of representatives. Pedro St. James Castle has been renovated and remains open to the public.
By 1835, slavery had been outlawed by Great Britain and the Cayman Islands led a quiet existence; much of the population worked as fishermen or building Cayman Islands turtle boats. The tranquil blue sea surrounding the Cayman Islands provided a livelihood for many residents, who then traded for agricultural items that could not be grown in the Cayman Islands. For example, palm thatch was transformed into marine rope and offered in barter for daily staples.
During this time, shipbuilding became a major industry in the Cayman Islands and for the next century, the Cayman Islands remained relatively isolated. Residents continued their traditions, but hurricanes, tidal waves, and a depletion of green turtles forced some residents to sail to neighboring countries to earn a living. The merchant seamen navigated the waters, which sustained the economy of the Cayman Islands until tourism and finance rose to prominence in the 20th century. During this time, the Cayman Islands were not only cut off geographically, but also lacked communication with the outside world; the first wireless station was not built until 1935.
The jump into the 20th century was aided by commissioner Sir Allen Cardinall, who served on the Cayman Islands from 1934 to 1940. Linking the public buildings of Grand Cayman with a network of roads, the commissioner was also the first public figure to recognize the tourism potential, even noting that one beach was “the most perfect bathing beach in the West Indies.”
In 1953, the first airfield in the Cayman Islands – the Owen Roberts International Airport on Grand Cayman was completed. A year later, an airstrip opened on Cayman Brac and within three years tourism began taking hold in the Cayman Islands, primarily along Seven Mile Beach.
By 1957 Bob Soto began the Cayman Islands’ first recreational diving business and introduced the world to the warm pristine waters surrounding the Cayman Islands. The Cayman Islands continued as a dependency of Jamaica with both as protectorates of Great Britain until 1962 when Jamaica became independent.
The Caymanians had a far different view of the Union Jack than their Jamaican neighbors and in 1962 a vote overwhelmingly favored the islands’ remaining a British dependency. To this day, the Cayman Islands are a self-governed British Colony and one of the most popular tourist destinations in the Caribbean.