|In or before 41 AC
|Son of Donnel Hightower
In 56 AC, Eustace and his brother, Ser Norman, accompanied Lady Elissa Farman, under the alias of Alys Westhill, on her voyage to discover new lands. Lord Donnel Hightower received a raven from the Iron Throne that Elissa was to be arrested and brought back to King's Landing in chains, but by the time Donnel acted, Eustace and his brother had already set sail from Oldtown.
After twelve days of sailing west and south of Westeros, the expedition began to suffer fierce storms. Some sailors on Eustace's ship, Lady Meredith, claimed that Norman's Autumn Moon was brought down by a kraken during one such storm. Elissa's Sun Chaser escorted Lady Meredith to three small uninhabited islands, Aegon, Rhaenys, and Visenya. Eustace turned east for home, while Elissa continued west for the unknown.
The hull of Lady Meredith was cracked by a leviathan during their return, so Eustace set sail for the Summer Isles but landed on Sothoryos. The knight spent a year repairing his ship on the continent, all the while his crew dwindled from diseases or unexplained disappearances. Hiring a new crew of Summer Islanders at high wages, Eustace eventually sailed Lady Meredith to Tall Trees Town. Nearly three years after departing, Eustace returned to Oldtown on Lady Meredith, gaunt and sunburnt but with very valuable cargo.