The Mayflower sets sail from Southampton, England on its first attempt to reach North America.

The Mayflower was hired in London, and sailed from London to Southampton in July 1620 to begin loading food and supplies for the voyage–much of which was purchased at Southampton. The Pilgrims were mostly still living in the city of Leiden, in the Netherlands. They hired a ship called the Speedwell to take them from Delfshaven, the Netherlands, to Southampton, England, to meet up with the Mayflower. The two ships planned to sail together to Northern Virginia. The Speedwell departed Delfthaven on July 22, and arrived at Southampton, where they found the Mayflower waiting for them. The Speedwell had been leaking on her voyage from the Netherlands to England, though, so they spent the next week patching her up.

On August 5, the two ships finally set sail for America. But the Speedwell began leaking again, so they pulled into the town of Dartmouth for repairs, arriving there about August 12. The Speedwell was patched up again, and the two ships again set sail for America about August 21. After the two ships had sailed about 300 miles out to sea, the Speedwell again began to leak. Frustrated with the enormous amount of time lost, and their inability to fix the Speedwell so that it could be sea-worthy, they returned to Plymouth, England, and made the decision to leave the Speedwell behind. The Mayflower would go to America alone. The cargo on the Speedwell was transferred over to the Mayflower; some of the passengers were so tired and disappointed with all the problems that they quit and went home. Others crammed themselves onto the already very crowded Mayflower.