Columbus at St. Ann's Bay.

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1492
Christovallo Colon, or Christopher Columbus, a Genoese, under the patronage of Isabella of Spain, set sail from Palos, with three vessels and ninety men, on the 3rd August. On the 11th October, he discovered St. Salvador, one of the Bahamas Islands.
1494
May 3, Jamaica discovered by Colombus on his second voyage to the New World. Approaching the shore in a southwest course from the eastern point of Cuba, he named the headland he first encountered, Santa Maria, from the name of his first ship, and landed at Ora Cabessa.
1503
June - Columbus shipwrecked on the northern coast of the island during the prosecution of his fourth voyage, where he was compelled to remain twelve months, and experienced severe sufferings from the mutinous conduct and desertion of a part of his crew. He named the place on which he landed, Santa Gloria, and St. Ann's Bay still marks the memorable spot.

Off the coast of Cuba, they were hit by yet another storm, the last of the ship's boats was lost, and one of the caravels was so badly damaged that she had to be taken in tow by the flagship. Both ships were leaking very badly now, and water continued to rise in the hold in spite of constant pumping by the crew. Finally, able to keep them afloat no longer, Columbus beached the sinking ships in St. Anne's Bay, Jamaica, on June 25, 1503. Since there was no Spanish colony on Jamaica, they were marooned.
Columbus and his men were stranded on Jamaica for a year. Diego Mendez, one of Columbus's captains, bought a canoe from a local Arawak chief and sailed it to Hispaniola. He was promptly detained by governor Ovando outside the city for the next seven months, and was refused use of a caravel to rescue the expedition.

In a desperate effort to get the natives to continue provisioning him and his hungry men, he successfully wowed the natives by correctly predicting a lunar eclipse, using astronomic tables made by Rabbi Avraham Zacuto of Spain. In addition half of those left on Jamaica staged a mutiny against Columbus, which he eventually put down. When Ovando finally allowed Mendez into Santo Domingo, there were no ships available for the rescue. Finally, Mendez was able to charter a small caravel, which arrived at Jamaica on June 29, 1504, and rescued the expedition.
Columbus returned home to Spain on November 7, 1504, his last voyage complete.


1509
First settlement by the Spaniards under Don Juan de Esquimel, lieutenant to Diego Columbus. He landed at Santa Gloria and fixed the seat of government there. He soon afterwards died, and was buried at Seville d'Oro. Esquimel (Old-Harbour) was named after him.
1523
St. Jago de la Vega founded by Diego Columbus, and in 1555 had the honour of giving the title of Marquis to his heir.
1525
Thirty sugar mills established in the island.
1526
St. Jago de la Vega plundered by Sir Anthony Shirley.
1635
Colonel Jackson, with five hundred men, landed and beat the Spaniards at Passage-Fort. They overran the island and exacted a considerable sum of money, then evacuated it, leaving behind them a number of deserters. Don Christopher Arnaldo Sasi, Governor.

The Spaniards brought African peoples and mixed with the local population.  They had children with the Africans and the Arawaks.
1655
May 3. The island taken by the English, under Admiral Penn and General Venables, after an unsuccessful attempt upon St. Domingo. The troops landed at Passage-Fort, and after a feeble opposition, the Spaniards were driven from their guns, and the British flag waved over one of the fairest islands in the world. —
Venables, on his return to England, was severely reprimanded by the council, sent a prisoner to the Tower, and dismissed from all his employments. Penn was also committed to the same place. They were liberated by the protector, on making their submission.
Major-General Sedgewicke sent by Cromwell to command the army.
1656
The council of state in England voted that 1,000 girls, and as many young men, should be listed in Ireland, and sent to the colony.
June 24. Sedgewicke died and the command devolved on Colonel D'Oyley, who executed Major Throgmorton for mutiny.
Dec. 14. General Brayne arrived with several transports and assumed the command.
General Stokes, with 1,600 men from Nevis, arrived and settled near Port-Morant.
1657
Sept. 2. Brayne died, and the command again devolved on Colonel D'Oyley.
Don Christopher Arnoldo Sasi landed at the north side, with all the former inhabitants, amounting to about five hundred men, and a reinforcement of one thousand from Old Spain, and built a fort of some strength on a rocky eminence near the sea at Rio Nuevo, in St. Mary's.
1658
June 22. D'Oyley, with five hundred picked men, attacked the fort, and completely routed the enemy.
They had three hundred privates, several captains, two priests and one sergeant-major killed; one hundred privates and six captains made prisoners; many wounded; they lost the royal standard and ten colours. The stragglers soon after quitted the island.
Colonel D'Oyley, with eight hundred men, sailed to the Spanish main and made a descent. He destroyed the town of Tolu, burnt ten galleons and loaded the ship with spoil.
Sept. 3. Cromwell died.
1660
Don Sasi attacked and defeated by a detachment under Colonel Tyson on the north side, where he had posted himself on a hill with one hundred and thirty men. He ultimately escaped from the island in a canoe from a small bay, which retains the name of Runaway Bay.
Twenty Spanish slaves surrendered with their commander, Juan de Bola, and were made free; their captain was presented with a commission to resume his command in the English service. Another party of negroes, called the Vermahollis gang, was destroyed by a detachment under Captain Ballard; and not more than fifty still held out.
Aug. 2. Conspiracy of the parliament men defeated by D'Oyley, at the head of the royalists, and Colonels Raymond and Tyson shot.
Aug. 14. Arrival of a man of war, with the union jack at the mast-head, which communicated intelligence of the Restoration, which had taken place on the 29th of the preceding May.
1661
May 29. The Diamond and Rosebush frigates arrived, bringing a commission from Charles II to D'Oyley, confirming him in the command of the island, with orders that the army should be immediately disbanded and settled throughout the country. The despatches contained also instructions for the constitution of judicial courts, with patents for the several departments of secretary, provost-marshal, and surveyor general.
June 5. Military government ceased - Colonel D'Oyley's commission proclaimed at Careening Point (Caguaya); and that town has ever since borne the name of Port-Royal, to commemorate the event.
A council of twelve members elected by the people; the island partially surveyed, and divided into twelve districts, viz:- St. David - St. Catherine - St. Andrew - St. John - St. Thomas - St. George - St. Mary - St. Ann - St. James - St. Elizabeth - Port-Royal - Clarendon.
1662
Two hundred settlers arrived in his majesty's ship, the Great Charity, and many more in the Diamond from the Windward Islands.
Aug. 11. Thomas Windsor Hickman, Lord Windsor (afterwards Earl of Plymouth), arrived as governor, with Sir Charles Lyttleton as chancellor and deputy-governor. A seal and mace for the island were brought by them.
D'Oyley ordered to England. He petitioned against the command, requesting delay, but it was refused, and he sailed in September.
Sept. 10. A royal proclamation published which gave every encouragement to the planters, and granted patents of land in free succage, by which several persons obtained titles to six, eight, ten, or twenty thousand acres each; Sir Thomas Lynch came into possession of very extensive domains, and Major Hope, with Colonels Archbould and Sir William Beeston, held the entire district of Liguanea between themselves.
Sept. 20. Lord Windsor fitted out an expedition of 1,200 men and eleven sail of the line against St. Jago de Cuba, who took the fort, demolished the fortifications and the town, consisting of two thousand dwelling houses, which they razed to the ground. The loss sustained by the enemy was probably not more than half a million sterling.
Oct. 6. During the absence of this expedition the militia was organized, and the Port-Royal regiment, well armed and accoutred, assembled for the first time, under the command of Lord Windsor as the colonel.
Oct. 22. The expedition returned from St. Jago de Cuba with much plunder.
Oct. 28. Lord Windsor sailed for England, leaving Sir Charles Lyttleton as lieutenant-governor.
A census taken of the population, which amounted to 4,355, including 552 negroes.
Fort-Charles erected.
1663
Feb. A proclamation issued offering freedom and thirty acres of land to such of the Spanish rebellious slaves as would submit to the command of Juan de Bola, their former chief; but whom they met on the 1st November, and engaged and destroyed.
An expedition sailed against Campeche, which sacked the town and took twenty sail of shipping, deeply laden with treasure.
At this period immense wealth rapidly flowed into the island, prizes daily arrived, and were publicly disposed of in defiance of a royal proclamation to restrain the corsairs, and the fame of one, unprecedented in its weight of quicksilver, resounded on the shores of Europe.
Dec. The first general assembly summoned by Sir Charles Lyttleton, and members returned for the following places, viz: - Yakallah, Robert Freeman, Richard Lloyd - St. Jago, Edward Waldron, Edward Mullens - Old Harbour, John Colebeck, Humphrey Freeman - Angells, Lewis Ashton - Cugua, W. Beeston, Samuel Long, Robert Byndloss - Seven Plantations, Anthony Collier - Guanaboa, William Clee, Thomas Freeman - Withywood, Richard Bryan -Dry River, William Ivy - Port Morant, Southwell Adkins - North side, Abraham Rutter.

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