In late March 1630, Winthrop and his fellow Puritans boarded eleven ships in Southampton harbor and sailed for their first stop at the Isle of Wight off the English coast. They were to depart on March 29, but unfavorable winds and strong seas kept them anchored until they finally embarked for the New World on April 8.

Winthrop, his three sons, and eight servants traveled aboard the flagship Arbella, a 350-ton ship formerly known as the Eagle, but now renamed for the wife of Isaac Johnson, the highest-born passenger of the fleet. (Winthrop was deeply saddened to leave his own wife behind, but they agreed to think of each other every Monday and Friday between five p.m. and six p.m. during communion.) In addition to the Winthrop party, the Arbella carried twenty-five of the most important passengers, seventy tradesmen, fifty- two seamen and fifteen officers.

The rest of the thousand-person expedition was spread among the other ten ships, with the Talbot, the Ambrose, and the Mayflower–not the Mayflower of Pilgrim fame, but another ship of the same name–carrying most of the passengers. Although they carried some passengers, the other ships–the Jewel, the Charles, the Trial, the Success, the Whale, the Hopewell, and the William and Francis–carried mostly livestock–240 cows and sixty horses–and freight for the new settlement in New England. The first four sailed first, and the other seven followed about three weeks behind.

Conditions on board the ships were horrible for the passengers, although they were certainly no worse than any other ship for the period. In fact, all eleven ships were veterans of the Mediterranean wine trade, and thus they were specially chalked and drier than most ships below decks. However, they could hardly be called comfortable. Above decks, the forecastle deck (on the forward part of the ship) housed the ship's crew, and the poop deck (at the rear) housed the officers. Most of the space in between was used for storage. The men made jury-rigged cabins for the women and children and hung hammocks from the ceiling for themselves. There was no ventilation below decks, no heat, no light at night, and only the most basic sanitary and cooking facilities. Since fresh water could not be kept clean and potable during long sea voyages, the ships carried beer for passengers to drink during the crossing. The Arbella alone carried forty-two "tuns," about 10,000 gallons of beer. For food, they ate salt pork.

On the very first day of the expedition, the four ships came upon what they thought might be a band of pirate ships. They hurriedly dismantled cabins to make room for the cannons, armed the men with muskets, and threw overboard most of the ships' bedmats, as the items were liable to catch fire. After much prayer and preparation, the small flotilla stood ready to do battle. Luckily, the suspicious ships were friendly, and the passengers would later regret getting rid of their sleeping materials so hastily. Two days later, the southernmost tip of Cornwall dropped behind them, and they had left England entirely behind. A week out of port, the group lost sight of the Talbot in one of the many storms the fleet faced during the crossing. They would not see it again until July 20, when it straggled into the New World twenty days after the rest of the fleet.

Throughout the passage, the Puritans huddled below decks and tried to weather the frequent storms. When one group of crewmembers grew too rowdy for the pious passengers, they held a prayer meeting and appointed three men to enforce proper conduct on board the ship. Winthrop occasionally convinced the seasick passengers to come out on deck and get a breath of fresh air. He found that a splash of salt spray often cheered up the passengers. Storms blew up with regularity and cost the expedition precious resources, both in material and in morale. One storm alone killed nearly seventy cows. Two servants aboard the Ambrose died in the crossing and a crewman on the Jewel perished as well.

On June 6, after sixty days at sea, the expedition sighted the coast of America at Cape Sable. Two days later, the group first laid eyes on New England when the crews spotted Mount Desert, on the modern-day Maine coast. On June 11, the ships cruised by the Isles of Shoals, where they could see a cluster of fishing boats working the seas, and they worked their way down to Cape Ann before anchoring for the night. The next morning, the Arbella sailed between Bakers Island and Little Island and into the mouth of Salem harbor. The journey was over.

As the ships laid anchor off Plum Cove, the passengers ran onto the deck and got their first glimpse of the shacks and hovels of Salem, a colony that at the time represented the finest New England had to offer in the way of civilization. After leaving their families and country behind, after two months at sea being tossed about by North Atlantic storms and eating food scraps, they could finally see that the hardest part of the trip lay ahead of them.

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