Alyn Oakenfist's voyage around Westeros

Alyn Oakenfist’s voyage around Westeros was a perilous royal mission disguised as an honor. After returning triumphantly to King’s Landing, Alyn Velaryon was knighted, given an admiral’s chain and a silver replica of the Queen Rhaenys, and invited to join the small council as master of ships. The king then assigned him to carry the royal fleet around Westeros and recover Fair Isle from Dalton Greyjoy’s ironmen. The appointment left Alyn little room to refuse: the task promised relief for the western coast, but also exposed House Velaryon’s strength to a series of formidable hazards before the fleet could reach its enemies.

A Royal Appointment and a Dangerous Commission

Seven days after Alyn’s return, the ceremony in the Red Keep celebrated his success before the king, the court, and half the city. Unwin Peake presented the admiral’s chain and silver ship, while the king asked Alyn to serve as master of ships. Alyn accepted. The royal request quickly turned into an order: raids by the ironborn were troubling the king’s western subjects, and Alyn was to take his fleet south around Westeros, win back Fair Isle, and end the threat.

The assignment served two purposes. If Alyn succeeded, Fair Isle would be restored to its lords and the westerlands spared further attacks; the campaign would also demonstrate the cost of defying the king and his new Hand. If he failed, the voyage could break the power of House Velaryon. Its route made that danger concrete: the Stepstones were hostile and politically unstable, Dorne offered no assured refuge, and Dalton Greyjoy was waiting in the Sunset Sea with a large fleet. The mission was not simply a contest between admirals. It tested whether Alyn could preserve his ships and men through a chain of negotiations, delays, and storms long enough to reach the ironborn.

As he left King’s Landing, Corlys Velaryon gave the king his elephant. Alyn returned to Hull to assemble the fleet and take on provisions, and said farewell to his wife, Baela Targaryen. She told him she was pregnant. Alyn proposed that a son be named Corlys, after his grandsire, and imagined the boy might one day sit the Iron Throne; Baela answered that, if the child were a girl, she would name her Laena, after her mother, and hoped she might one day ride a dragon. Their exchange set a private family future beside the uncertain course of the expedition.

Passage Through the Stepstones

Alyn approached the Stepstones more cautiously than on his earlier visit. Rather than commit the fleet blindly, he sent scouts disguised as fishing boats and merchantmen to learn who controlled the islands and their waterways. Their reports described a divided sea: Racallio Ryndoon held Bloodstone and the southern islands, while Pentoshi sellswords serving the Archon of Tyrosh occupied the rocks to the north and east. Booms and the wrecks of ships blocked many channels; Ryndoon and his followers controlled those still open. Alyn therefore had to choose between forcing a passage and bargaining for one.

He chose negotiation, judging that a battle could cost him half his strength when he would need every available man against the Red Kraken. Taking the Lady Baela, he sailed under a parley flag to Bloodstone to seek free passage for the fleet. Ryndoon kept him for more than a fortnight at his wooden fortress. The character of the visit remained uncertain even to Alyn: his host alternated between treating him as a friend and considering whether to kill him. The negotiations included tests of loyalty and acts of violence, but Alyn’s purpose remained practical—secure a route through Ryndoon’s waters without spending the strength needed for the larger campaign.

Ryndoon eventually named his price: three ships, an alliance written on sheepskin and signed in blood, and a kiss from Baela. Alyn gave him the fleet’s three least seaworthy ships, offered an alliance on parchment with a maester’s signature, and promised a kiss from Baela if Ryndoon visited Driftmark. The compromises were enough. The fleet passed through the Stepstones, although its safe passage depended on an agreement whose terms Alyn had deliberately reshaped.

Dorne and the Cost of Resupply

The next difficulty was Dorne. The appearance of a large Velaryon fleet off Sunspear alarmed the Dornish, who had little naval strength with which to oppose it. Aliandra Martell chose to receive Alyn as a visitor rather than an attacker. She met him with a dozen favorites and suitors; the young princess was reportedly impressed by the admiral, celebrated as the Hero of the Stepstones. Their interests were distinct but compatible in the short term: Alyn needed fresh water and provisions, while Aliandra sought his company. The accounts disagree over whether he returned her personal attentions. They agree that her favor displeased Dornish lords and angered her younger siblings.

Alyn nevertheless obtained what the fleet needed: water, food sufficient to reach Oldtown and the Arbor, and charts marking dangerous whirlpools off Dorne’s southern coast. This resupply enabled the voyage to continue, but Dornish waters also brought its first losses. A storm off the drylands west of Salt Shore scattered the fleet and sank two ships. Farther west, near the mouth of the Brimstone River, a damaged galley stopped for water and repairs. Bandits attacked it at night, killed its crew, and took its supplies. The hazards were different, but each showed how a fleet could be diminished without meeting a rival navy: weather scattered ships, while the need to stop for repairs exposed them to attack.

Oldtown: Ships, Charts, and Support

The losses were more than made good at Oldtown. Guided by the great beacon atop the Hightower, the fleet entered Whispering Sound, where Lyonel Hightower welcomed Alyn. Alyn’s courteous treatment of Samantha Hightower helped win Lyonel’s friendship, and the two young men’s relationship eased old hostility between the Blacks and Greens. Lyonel promised twenty warships for the expedition, while Lord Redwyne of the Arbor pledged thirty more. The fleet’s prospects improved sharply through hospitality and political connection rather than combat.

Alyn stayed longer than intended while waiting for Redwyne’s galleys. In Oldtown, he explored the city’s ancient ways and visited the Citadel, spending days studying old charts and Valyrian treatises on warship design and naval tactics. At the Starry Sept, the High Septon blessed him for the campaign against the ironborn and their Drowned God. While Alyn was there, news arrived of Queen Jaehaera’s death, followed within days by the king’s betrothal to Myrielle Peake. Alyn grew close to Samantha as well as Lyonel, though whether he helped write Samantha’s notorious letter remained uncertain. He also sent letters to Baela on Driftmark; their contents are not known.

At last, impatient with the delay, Alyn ordered the fleet to sail without waiting any longer for Lord Redwyne. Oldtown cheered as the ships departed down Whispering Sound. Twenty Hightower war galleys accompanied them under Ser Leo Costayne, known as the Sea Lion. The expedition had gained a substantial ally, but the missed Redwyne reinforcements also marked the limit of Alyn’s willingness to let preparation become postponement.

Into the Sunset Sea

The fleet turned north into the Sunset Sea off Blackcrown, then followed the western coast past Bandallon. At the mouth of the Mander, galleys from the Shield Islands joined them: three each from Greyshield and Southshield, four from Greenshield, and six from Oakenshield. The growing fleet was again struck by a storm. One ship sank, while three others suffered damage severe enough to prevent them continuing. Alyn regrouped off Crakehall, where the lady of the castle came out to meet him and told him of the great Maiden’s Day ball.

By then, Dalton Greyjoy had been warned of Alyn’s approach and gathered his forces. Hundreds of longships assembled south of Fair Isle, with more near Feastfires, Kayce, and Lannisport. Dalton spoke of defeating Alyn and then turning his fleet back along the route he had taken, attacking the Shields, Oldtown, and Sunspear, and claiming Driftmark. He also threatened to take Baela as a salt wife. The scale of those ambitions made the expedition’s stakes unmistakable: Alyn was not merely sailing to recover an island, but facing a hostile power that imagined its victory as the beginning of a wider campaign.

The voyage’s account ends as the opposing fleets prepare for their encounter, not with the battle’s result. Its movement from royal ceremony to passage negotiation, resupply, alliance-building, and storm damage makes clear that the contest with Dalton Greyjoy began well before the ships met. Alyn’s strength depended on keeping his fleet intact and adding allies along the way; each delay or loss narrowed the margin for the confrontation ahead.