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The last time someone seriously considered crossing the Sunset Sea was Elissa Farman. She took a year to build her ultra-ship using gold she got from selling three dragon eggs (absurdly expensive).

She had the best crew with her and support from the Hightowers who were the second best sea faring Lords after the Velaryons.

Arya clearly didn't have enough time or the gold for this kind of preparation. How does she expect to not just die in the middle of the sea?

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    “Arya clearly didn't have enough time or the gold for this kind of preparation” — we don’t know when she actually set sail. For all we know, it could have been two years since she said goodbye to Jon on the Kings Landing docks.
    – Paul D. Waite
    May 22, 2019 at 7:10
  • Bittersweet ending y'all
    – KharoBangdo
    May 22, 2019 at 7:21
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    Or is she doomed to be the main character in a spin off series?
    – Todd Wilcox
    May 22, 2019 at 7:57
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    "Drogon no swiping!"
    – Valorum
    May 22, 2019 at 8:19
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    @ToddWilcox Arrrrrya would probably become best known pirate of all times. (Not my invention)
    – user1129682
    May 22, 2019 at 10:31

2 Answers 2

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According to A Wiki of Fire and Ice,

When he returned to Oldtown on Lady Meredith in 59 AC, Eustace Hightower explained that they had sailed south by southwest years ago but lost Norman and his Autumn Moon to a storm. Elissa's crew towed Lady Meredith to three exotic islands, which she named Aegon, Rhaenys, and Visenya. Despite the protests of Eustace, Elissa continued westward on Sun Chaser and was never seen again. Many years later, during his second great voyage on Sea Snake, Corlys Velaryon believed he saw the old, weathered Sun Chaser in Asshai. It is therefore possible that Elissa reached Essos by sailing west from Westeros.

The Wiki quotes Fire & Blood as the source of this information.

From this we can learn:

  1. Elissa sailed mostly south before turning west, so there could very well be large islands or even a continent more directly towards the west, where Arya is sailing.
  2. She did encounter three exotic islands - and where there are three, there are likely more.
  3. There is some evidence that her ship did manage to circumnavigate the globe, at least as far as Essos. If this evidence is true, Arya could well duplicate the feat and even return to Westeros from the east - quite a feat.
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While it is clearly speculation or future work issue to say if she will succeed, it is safe to answer that

No !
Arya the explorer is not doomed to failure.

Mostly because of the Plot compass.
If the story needs it, Arya will find a way that Elissa didn't.

But in a more realistic way. Islands tends to be small in big oceans. Sailing 100 km north or south can change everything. It can transform a failure due to famine and diseases to a re-supply.

It's impossible to say if she will succeed or not yet.
But it's impossible to say that she will fail because someone failed before her.

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