The fleet consisted of seven ships: The galleass Tiger (Grenville's flagship, with Fernandes as pilot), the flyboat Roebuck (captained by John Clarke), Red Lion (under the command of George Raymond), Elizabeth (captained by Thomas Cavendish), Dorothy (Raleigh's personal ship, perhaps captained by Arthur Barlowe) and two small pinnaces.

On April 9, 1585, the fleet departed Plymouth, heading south through the Bay of Biscay.
A severe storm off the coast of Portugal separated Tiger from the rest of the fleet, and sank one of the pinnaces.
Fortunately, Fernandes had advised a plan for such an occurrence, wherein the ships would meet up at Mosquetal, on the south coast of Puerto Rico.
Proceeding alone, Tiger made good speed for the Caribbean, arriving at the rendezvous point on May 11, ahead of the other ships.

While awaiting the fleet, Grenville established a base camp, where his crew could rest and defend themselves from Spanish forces.
Lane's men used the opportunity to practice for building the fortifications that would be needed at the new colony.
The crew also set about replacing the lost pinnace, forging nails and sawing local lumber to construct a new ship.
Elizabeth arrived on May 19, shortly after the completion of the fort and pinnace.

The remainder of the fleet never arrived at Mosquetal.
At least one of the ships encountered difficulties near Jamaica and ran out of supplies, causing its captain to send twenty of his crew ashore.
Eventually Roebuck, Red Lion, and Dorothy continued to the Outer Banks, arriving by mid-June.
Red Lion left about thirty men on Croatoan Island and departed for privateering in Newfoundland.
In the meantime, Grenville established contact with local Spanish authorities, in the hopes of obtaining fresh provisions.
When the Spanish failed to deliver the promised supplies, Grenville suspected they would soon attack, so he and his ships abandoned the temporary fort.

Grenville captured two Spanish ships in the Mona Passage, adding them to his fleet.
Lane took one of these ships to Salinas Bay, where he captured salt mounds collected by the Spanish.
Lane again built fortifications to protect his men as they brought the salt aboard.
 Grenville's ships then sailed to La Isabela, where the Spanish set aside hostilities to trade with the well-armed English fleet.
On June 7, Grenville left Hispanola to continue to the Outer Banks.

The fleet sailed through an inlet at Wococon Island (near present-day Ocracoke Inlet) on June 26.
Tiger struck a shoal, ruining most of the food supplies and nearly destroying the ship.
There are indications that Grenville's fleet was supposed to spend the winter with the new colony, perhaps to immediately begin using it as a privateering base.
The wreck of Tiger, however, made that impossible.
The remaining provisions could not support a settlement as large as had been planned.
Moreover, the shallow inlets of the Outer Banks made the region unsuitable for a base to support large ships.
The colony's top priority would now be to locate a better harbor.

After repairs, Tiger continued with the rest of the fleet to Port Ferdinando, where they reunited with Roebuck and Dorothy.
The men left behind by Red Lion were presumably also located during this time.
On August 5, John Arundell took command of one of the faster vessels and set sail for England, to report the expedition's safe arrival.
The fleet consisted of seven ships: The galleass Tiger (Grenville's flagship, with Fernandes as pilot), the flyboat Roebuck (captained by John Clarke), Red Lion (under the command of George Raymond), Elizabeth (captained by Thomas Cavendish), Dorothy (Raleigh's personal ship, perhaps captained by Arthur Barlowe) and two small pinnaces.
On April 9, 1585, the fleet departed Plymouth, heading south through the Bay of Biscay. A severe storm off the coast of Portugal separated Tiger from the rest of the fleet, and sank one of the pinnaces. Fortunately, Fernandes had advised a plan for such an occurrence, wherein the ships would meet up at Mosquetal, on the south coast of Puerto Rico. Proceeding alone, Tiger made good speed for the Caribbean, arriving at the rendezvous point on May 11, ahead of the other ships.
While awaiting the fleet, Grenville established a base camp, where his crew could rest and defend themselves from Spanish forces. Lane's men used the opportunity to practice for building the fortifications that would be needed at the new colony. The crew also set about replacing the lost pinnace, forging nails and sawing local lumber to construct a new ship. Elizabeth arrived on May 19, shortly after the completion of the fort and pinnace.
The remainder of the fleet never arrived at Mosquetal. At least one of the ships encountered difficulties near Jamaica and ran out of supplies, causing its captain to send twenty of his crew ashore. Eventually Roebuck, Red Lion, and Dorothy continued to the Outer Banks, arriving by mid-June. Red Lion left about thirty men on Croatoan Island and departed for privateering in Newfoundland. In the meantime, Grenville established contact with local Spanish authorities, in the hopes of obtaining fresh provisions. When the Spanish failed to deliver the promised supplies, Grenville suspected they would soon attack, so he and his ships abandoned the temporary fort.
Grenville captured two Spanish ships in the Mona Passage, adding them to his fleet. Lane took one of these ships to Salinas Bay, where he captured salt mounds collected by the Spanish. Lane again built fortifications to protect his men as they brought the salt aboard.  Grenville's ships then sailed to La Isabela, where the Spanish set aside hostilities to trade with the well-armed English fleet. On June 7, Grenville left Hispanola to continue to the Outer Banks.
The fleet sailed through an inlet at Wococon Island (near present-day Ocracoke Inlet) on June 26. Tiger struck a shoal, ruining most of the food supplies and nearly destroying the ship. There are indications that Grenville's fleet was supposed to spend the winter with the new colony, perhaps to immediately begin using it as a privateering base. The wreck of Tiger, however, made that impossible. The remaining provisions could not support a settlement as large as had been planned. Moreover, the shallow inlets of the Outer Banks made the region unsuitable for a base to support large ships. The colony's top priority would now be to locate a better harbor.
After repairs, Tiger continued with the rest of the fleet to Port Ferdinando, where they reunited with Roebuck and Dorothy. The men left behind by Red Lion were presumably also located during this time. On August 5, John Arundell took command of one of the faster vessels and set sail for England, to report the expedition's safe arrival.
Roanoke Colony