Oldtown
Oldtown is the oldest and one of the most powerful cities in the Seven Kingdoms, the seat of the Citadel where maesters are trained and forged in their chains of many metals. It is to this ancient city of learning that Jon Snow sends Samwell Tarly and Maester Aemon, partly to protect the frail, blind maester from the red priestess Melisandre, who might seek king's blood for her fires, and partly to have Sam forge a maester's chain so that the Night's Watch might have a new maester when Aemon dies.
The Citadel and the Maesters' Chain
The Citadel is the great center of learning in Westeros, where men study to become maesters. To earn a maester's chain, a candidate must master various disciplines, including healing, ravenry, history, and the forging of links of different metals. Samwell Tarly is sent there by Jon Snow to become a maester, despite his fear of cutting up corpses and his father's opposition to the life of a maester. Jon commands him: "You'll go to the Citadel and forge a chain, and if you have to cut up corpses, so be it." Sam protests that his father, Lord Randyll Tarly, forbids any son of House Tarly from wearing a chain, but Jon reminds him that his life now belongs to the Night's Watch.
The Journey and the Purpose
Jon Snow sends Sam and Maester Aemon south from Castle Black to Eastwatch-by-the-Sea, where they are to take ship for Braavos and then arrange their own passage to Oldtown. The journey is intended to keep Aemon safe from Melisandre, who might require king's blood for her spells, and to allow Sam to begin his training at the Citadel. Jon also hopes that the singer Dareon, who will join them at Eastwatch, might win men for the Watch with his songs in the south. Sam is to take Gilly and her child with him, passing the boy off as his own bastard to protect him.
The Significance for the Night's Watch
Oldtown represents the hope of renewal for the Night's Watch, which has lost too many of its best men, including Maester Aemon. Jon Snow recognizes that the Watch has hundreds of men who can loose an arrow but only a handful who can read or write, and he needs Sam to become his new maester. The Citadel also holds vast libraries that Sam might use to research the Others, though Jon acknowledges that the oldest histories were written after the Andals came and may be unreliable. The journey to Oldtown is thus both a strategic necessity and a personal mission for Sam, who must overcome his fears to serve the Watch in a new capacity.