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Pirates in Paradise

There once was a mythical time when brave and dangerous pirates sailed the seas in search of both fortune and fame. In this time heroic villains rose to fame, figures like Blackbeard, Captain Kidd, Captain Avery, Captain Morgan and others became household names. They were the famous anti-heroes of their time. This was also a historical period from roughly 1680 - 1730 when large numbers of Anglo-American mariners were engaged in piracy and privateering, often against Spanish or other targets of opportunity in the Atlantic Ocean.

Spanish explorers first set foot on this area in the early 1500's. Key Largo is the first island in the long line moving away from the Florida mainland. The Spaniards named it "Cayo Largo" (Long Key) because it was such a large island. Over the years it has been a haven for pirates and smugglers and many shipwrecks occurred near its shores.

Island Name and Name History
In 1687, the name Cayo Largo (Key Largo) was first on a document. This document was an interrogation of an English pirate named Ralph Wilkinson Before that the name “Caio dos 12 Lingoes” appeared on charts as the name referring to this area. The first map with the name Key Largo
is dated 1733.  The name, Key Largo is translated as “large or long”. It is both. It is the largest and longest key in the keys.

Hurricane of  1733

 1733 – On July 15th a 22-ship treasure fleet was struck at the Keys by hurricane, leaving 13 ships sank or grounded, forever, in the 80 miles between Elliott Key and Key Vaca.  After the storm perhaps a thousand people were left to survive for days on their sorry hulks or on the islets until help from Havana could arrive. One of North America’s greatest maritime disasters, it was unknown in our  history until 1938, when diver Art McKee began his underwater and archival investigations of a “cannon wreck” shown to him by Islamorada fisherman Reggie Roberts. 

Spanish and English explorers looking to colonize new lands and discover trading partners.  The “Age of Exploration” helped create a trade route between Europe and Central and South America with a port stop in Cuba, which is 90 miles south of Key West.

The Florida Keys, the southernmost regions were dominated by the Tequestas and the Calusas indians. They lived off of the rich abundance of food from the sea and the fertility of the coastal lands.

"The Keys," were an early fixture on nautical maps. The year 1763 marked the Spanish claim to Florida. The King of Spain proclaimed the islands a part of Cuba, which provided a way to keep the islands, rich in fish, turtles and mahogany for shipbuilding.

The Keys remained remote and inaccessible until well into the 20th Century, but that only added to the intrigue and fascinating tales of pirates, buried treasures and shipwrecks that litter their history.

Henri Caesar "Black Caesar" was born in the mid-1760's to Haitian slaves owned by a wealthy French planter named Arnaut. He spent his chilhood performing various tasks inside as a houseboy, but was later moved to the lumberyard in an effort to employ his larger physique.

Pirates have been figures of fascination and fear for centuries. The most famous buccaneers have been shrouded in legend and folklore for so long that it's almost impossible to distinguish between myth and reality. But what was life really like for an early 18th-century pirate? The answer: pretty grim. It was a world of staggering violence and poverty, constant danger, and almost inevitable death.

 Florida contains more buried and sunken treasures Florida has a fascinating and romantic history. Seven different flags have flown over her, not to mention the black flag of the pirates. Florida became the haven of many notorious pirates, including Blackbeard, Lafitte, Gasparilla, Kidd, Rackham, Black Caesar, Bowlegs, Bonnett, and possibly even Morgan himself. They roamed the waters of the Caribbean Sea, and captured every ship in sight. Often, they brought their loot back to Florida, and buried it on some lonely shore. When they finally died, the location of their hidden wealth died with them. The majority of all buried treasure in Florida is the work of pirates.

One of the most vicious pirates to rove the Spanish Main and coastal waters of Florida in the early 19th century was Henri Caesar. Familiarly known as Black Caesar. While he was wise enough to limit his raids to small ships and defenseless villages, Caesar amassed a great amount of plunder, which historians claim to be still hidden at no less than six different Florida coastal sites.

The legend of Black Caesar describes an African leader who, after being tricked into the hold of a slave ship and transported to the Caribbean, escaped and became a pirate. Black Caesar is said to have roamed the keys, raiding and marauding at will. Caesar Creek (located just to the southeast of the present-day Adams Key Information Center) is thought to have been the location of Black Caesar's headquarters. Legend identifies him as a tall African chief with great strength and keen intelligence. A conniving captain lured him and his warriors aboard a slaver with greater treasures than the gold watch that fascinated Caesar. Once on board, the captain and his men plied the Africans with food while enticing them musical instruments, jewels, silk scarves, and furs. With his focus on these unusual treasures, Caesar failed to notice that the slaver put to sea. Upon learning the truth, he and his men fought the ship’s crew, but the slavers eventually subdued the Africans.

During his confinement, Caesar refused to eat or drink. One sailor showed Caesar kindness, and the two eventually became friends. When the slaver wrecked on the reefs off Florida, the sailor freed Caesar, and the two escaped in a long boat loaded with supplies and ammunition. They left the others to die.

Caesar and his friend decided to attack passing ships. Whenever one was spotted, they rowed the long boat near the vessel and pretended to be shipwrecked sailors. Once aboard their victim, they seized control and took their treasure ashore. Eventually, they buried a large cache of booty somewhere on Elliott Key, Black Caesar the pirate, who ambushed sailing ships passing his refuge at present-day Caesar Creek. Local folklore recounts tales of his buried treasure, cruelty and daring raids.

Located less than a mile from the ocean shore off Lower Matecumbe, 305-664-4815.
A 12-acre lush with tropical vegetation. The island's former inhabitants included New York seaman John Jacob Housman, who in 1831, established a colony of homes laid out along paved streets with a lavishly landscaped central courtyard in 1840, the island was raided by hostile Indians and most of the buildings were destroyed.


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Captain John Phillips's  PIRATES CODE   -  Captain John Phillips was the captain of the Revenge, who also set a code for his men in 1724;

I. Every Man Shall obey civil Command; the Captain shall have one full Share and a half of all Prizes; the Master, Carpenter, Boatswain and Gunner shall have one Share and quarter.

II. If any Man shall offer to run away, or keep any Secret from the Company, he shall be maroon’d with one Bottle of Powder, one Bottle of Water, one small Arm, and Shot.

III. If any Man shall steal any Thing in the Company, or game, to the Value of a Piece of Eight, he shall be maroon’d or shot.

IV. If any time we shall meet another Marrooner that Man shall sign his Articles without the Consent of our Company, shall suffer such Punishment as the Captain and Company shall think fit.

V. That Man that shall strike another whilst these Articles are in force, shall receive Moses’s Law (that is, 40 Stripes lacking one) on the bare Back.

VI. That Man that shall snap his Arms, or smoak Tobacco in the Hold, without a Cap to his Pipe, or carry a Candle lighted without a Lanthorn, shall suffer the same Punishment as in the former Article.

VII. That Man shall not keep his Arms clean, fit for an Engagement, or neglect his Business, shall be cut off from his Share, and suffer such other Punishment as the Captain and the Company shall think fit.

VIII. If any Man shall lose a Joint in time of an Engagement, shall have 400 Pieces of Eight ; if a Limb, 800.

IX. If at any time you meet with a prudent Woman, that Man that offers to meddle with her, without her Consent, shall suffer present Death.

While pirates and privateers were a constant threat to the treasure fleets, hurricanes became a greater enemy. The torrential rains and violent winds whipped the seas into savage furies that destroyed more ships, claimed more lives, and engulfed more treasure than the outlaws who preyed the high seas.

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 Pirates at the Keys
By Gail Swanson

      In January, 1682, a ship named Nuestra Senora de Candelaria left St. Augustine for Vera Cruz, Mexico, to get the yearly subsidy given to the town.  St. Augustine, always poor, was financially supported by Spain’s government at Mexico, because of St. Augustine’s supposed protection of the treasure galleons that left Vera Cruz and sailed home via the Florida coast.  Around February 10th the Candelaria was captured by 5 French pirate vessels after running aground at the Upper Keys.
     Research of the documents of around that time has revealed more pirate activities, and the meeting at the Keys of some of the most feared pirate leaders ever.  We can now substitute pirate lore (there are NO documents to support the Black Caesar-at-the-Keys story) for historical documents  on pirates such as Lorencillo .
     For an overview of these activities, the following is a chronology of pirate attacks at Florida and Mexico during a 4-year period,  1681-1684:


     In June Governor of Florida Juan Marquis Cabrera wrote to the King of Spain that he has been expecting the enemy (pirates) all spring.  That from Havana he is warned that the pirates design to assemble at Cayo de Guesas (the Key of Bones – Key West) to invade and sack St. Augustine.


      Five French pirate ships take the St. Augustine subsidy ship, the Candelaria, which was under the command of Salvador de Cigarroa, at the Upper Keys (February).
 French pirates (2 ships, 100 men) repeatedly attack the Apalachee fort 9 miles up the St. Marks River, Apalachee Bay, Florida Panhandle (March – June).  Fighting in defense there was Sgt. Major Salvador de Cigarroa, who had been released by the pirates after his capture at the Keys.  Later, captives from the Apalachee fort, Pedro de Arcos and Francisco Hernandez, were released on the coast of Cuba and gave testimony in St. Augustine in August of what they had learned as captives of the pirates.  That 5 English and French pirate captains, including Lorencillo (Laurens de Graff) had met in the Keys and planned to join forces under Monsier Agramon (the Sieur de Grammont) and attack St. Augustine.


     French and English (Bahamian) pirates were on the Cuban coast seeking a certain lost treasure ship.  The French were in the 3-gun long boat La Fortune (The Fortune), with 36 men commanded by Capt. Abraham Briac.  They had obviously been on the Florida coast and probably at the Keys for aboard their ships were 18 Florida Indian divers.  Some  of these pirates were captured by the Spanish and gave intelligence of their planned attack on St. Augustine (January).
     French and English pirates (lead by Frenchman Grammont) threaten St. Augustine, but were repelled, but took nearby Matanzas and other posts of San Juan and Santa Maria (March-April).
     Pirates 800 strong under 8 Dutch and French captains including  Lorencillo, Grammont, and Van Horn, attacked Vera Cruz.  It was a brutal raid, with the pirates locking 5,000 people in the church; many died, especially children.


     Another subsidy ship from St. Augustine for Vera Cruz, the Plantanera, was captured by English pirates under Thomas Jingle and Andrew Ranson, at the Keys.
     Sent to reconnoiter the Keys looking for pirate ships seen off Havana, Miguel Ramon and men sighted them near Key Biscayne, and engaged in battle.  Ramon and his crew were captured, tortured by Andrew Ranson, then Ramon was set free on one of the Keys.
     Captured sacking Tampico in April, a pilot of the pirates named by the Spanish Juan Poule (possibly John Poole or John Powell) was spared by the Spanish, apparently for his knowledge of the coast.  Three years later he was at Key West with a Spanish  force sent to probe the Gulf Coast looking for the settlement of Frenchmen led by LaSalle. Poule/Poole had been at Key West before, long enough to make turtle crawls, which he showed the Spanish.  Could it be that he was at the referred pirate meeting at Key West in the early 1680s?

     We now, since the 1990s, have at Keys libraries copies of two of the 1680s Spanish documents that record the pirates at the Keys; the third, on Andrew Ranson & Miguel Ramon, has not yet been copied from the archives.
     In 1991 Jim Clupper of Islamorada copied the letter of Governor Cabrera, dated 1681, from a collection of Spanish documents in North Carolina.  It is 27 pages long, and  very difficult to read.  The summary of its contents, in English, contains the warning of the pirates assembling at Key West.  I found in 9 continuous pages of the letter Cayo de Guesos (Key West) written 3 times.  The facts I could glean were few, but follow:
     The ships involved were: 1. the Mercader, with a half French and half English (from London) crew, 2. The frigate La Paloma (in English, The Pigeon) and 3. A lesser bark (ship) named La Fortuna (The Fortune – see 1683!!!)…“todos en otro Caiyo de Guesos” - “all in the other Key of Bones”.  On the next page of the document is the phrase “tundar en Cayo de Guesos” - “aground at Key of Bones”.  Four pages after this is again “Caio de Guesos” and  names of more ships, 4. the frigate Jesus Maria y _______ (unreadable) and 5. Nuestra Senora de la ______ (unreadable). 
      The second document, also a letter by Governor Cabrera, is dated the next year, 1682.  It is part of the Stetson Collection of Spanish documents.  I copied 15 pages of it at University of Florida in Gainesville.  This is the account of the attack upon the Candelaria.  I do not have the language skills to translate all of this account, but from phrases that I could transcribe from the ancient handwriting and could translate the following story emerged.  Of course, a better, thorough translation would reveal more details.
      The Candelaria encountered bad weather after leaving St. Augustine and was sailing down the Keys inside of the reef when it ran aground at Las Playuelos (in English, “Little Beaches” - an Upper Keys location noted on the Lanzas 1743 and the Jeffreys 1763 maps).  The Candelaria may have been in company with another Spanish ship or else met one coming northward, for there is a second grounding noted at Bocas de Guerrero (Mouths of the Warrior), now named Tavernier Creek.  Two pirate ships found them, burned at least one of the Spanish ships, and then were joined by 3 more pirate ships.  There was a battle, perhaps between the pirates themselves.  The pirates took all the people except for 5 men who hid, one of them a slave and two of them English.  From one of the declarations included in Cabrera’s letter. 
      “The other enemy burned the ship and in this time slipped away two Englishmen that we carried to this presidio [of St. Augustine] and having arrived three ships of the other enemy...they [the people] determined to surrender themselves and this deponent and the other four determined to stay hidden as it were...until the other ships went away, 3 to the north and 2 to the south, taking away all the people and that [the enemy] having sacked the other frigate this deponent and the other four companions from a log that they found they made a canoe and came to this presidio.”   The log that they found was on one of the keys called Matecumbe, according to another deposition.  Two other place names occur in the document, Cayo Largo (Key Largo), and Cayo Buscain (Key Biscayne).
     If indeed the rumored pirate meeting at Key West took place to plan an attack on St. Augustine it seems the other attacks would have been planned at that time as well.  It could have been one of the most important pirate meetings in the heyday of Caribbean pirates.

 Sources:  Copies of the two Cabrera letters are at the Islamorada library; a copy of the 1682  letter filed in Archivo General de Indies in Spain as (54-5-12/5)  and notes only on the 1681 letter (AGI 58-1-26) are at the Key West library, in the “Swanson Drawer”.  Important information has come from the following: Robert Weddle, LaSalle, The Mississippi and The Gulf:  Three Primary Documents (1987) - on John Poole; Amy Turner Bushnell, “How to Fight a Pirate…” in Gulf Coast Historical Review #5 (Spring, 1990) - on the attack on Apalachee and knowledge of the Keys meeting of Lorencillo; J. Leitch Wright Jr., “Andrew Ranson:  Seventeenth Century Pirate?“ in Florida Historical Quarterly Vol 39 (1960-1961).   For the attack on St. Augustine see Luis R. and Eugenia B. Arana, “Pirates March on St. Augustine, 1683”, El  Escribano, Vol 2, 1972,  (My thanks to Tom Hambright for copying this article for me in Jacksonville.)  For the attack on Vera Cruz a translation of the 1683 letter of Friar Juan de Avila to Friar Agustin de Betancur by Leopold D. L. Zea of Mexico was printed in No Quarter Given, May, 1998.

A shipwreck park named after the sunken Spanish ship "San Pedro", the underwater park is located under 18 feet of water approximately 1.25 nautical miles south from Indian Key. In 1773, the San Pedro, sailing under the Spanish flag, wrecked and went to the bottom off the Florida coast. The remains of the 287-ton San Pedro rest on a white sand pocket -- the home of sea creatures living amidst ballast stones and coral heads.
A small tropical oasis right on US soil, the Florida Keys. It  has long been a haven for tourists of every kind. You name it, and chances are someone has gone there looking for it… from the infamous Fountain of Youth, to sunken pirate's treasures, to artistic inspiration, to the catch of the day.The Florida Keys will always be an exotic world of tropical adventure to those who visit, and a special tropical paradise to those who who are lucky enough to stay. 



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    Ocean Pointe Marina


    Ocean Pointe Vacation This upscale Condominium Resort is located directly on the Ocean in Key Largo. Offering a beautifully decorated condo, with two bedroom - two bath with whirlpool tubs for weekly and monthly rentals Ocean Pointe Suite is located,about one hour drive south from Miami international Airport,The hard Rock Cafe-Casino,the Art Deco South Beach and Miami shopping.
    About 90 miles east of Key West.

    Rates (in US Dollars )
    Sep 01-Dec 15 ... $125/night .. $ 800/week. (3 night min)
    Dec 16-Aug 31 ... $150/night .. $ 950/week. (3 night min)
    Holidays ........ $200/night .. $1100/week. (3 night min)
    Special Events .. $200/night .. $1100/week. (3 night min)
    Special Events includes Mini + Open Lobster Season.
    20 % deposit required to make a reservation.
    Refundable up to 30 days before arrival date.
    Note: Until confirmed, rates are subject to change without notice.


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    Key Largo is known as the "Diving Capital of the World" while Islamorada is called the "Sport Fishing Capital".


    Key Largo Getaway


    Vacation Property
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    Key Largo is known as the "Diving Capital of the World" while Islamorada is called the "Sport Fishing Capital".