What is the most difficult city in Planetos to conquer?

[Ser Snowflake]

There have been numerous threads on the strongest castles, but not many on the strongest city. I'm interested in people's response to this question, because my top 5 do not include a single city from Westeros.

1. Qarth--the triple walls of the Qarth seems to be very formidable. I cannot fathom how any dragonless force could take the city by land. The Qartheen also control the Jade gates, so a siege by sea seems unlikely. The only naval force large enough to take them would probably be the Iron Fleet or the Purple ships of Braavos, but any force of that size would likely not make it all the way to Qarth in one piece.

2. Braavos-- Almost on the same level of Qarth as there isn't an enemy within miles with the power to try to provoke the Titan of Braavos. The ships of the Summer Islands are formidable, but they are a peaceful folk, thousands of miles away. 

3.  Volantis--The Black Wall of Old Volantis is nearly as formidable as the triple walls of Qarth. The Dothraki are a threat,but they lack the siegecraft to starve out the Volantenes, and if push come to shove the Volantenes could always dine on their slaves if the situation get too dire.

4. Nefer--I don't know much about the secret city, but it's reputation would be enough to deter me. The city is shrouded in fog, almost entirely underground, and populated by torturers and practioners of the dark arts.  

5. Asshai-By-The-Shadow-- see Nefer.....I'm not sure I would even trade in Asshai if I owned a fleet of ships. The city has no children. Why? And why do the Asshai have to import all of their food..... because the grass is inedible? IMO Asshai is not a place for any decent folk. Ser Jorah must know something about Asshai that we don't know....why would he suggest Dany go there? Was he still working for Varys then?

 

The reason for no Westerori cities in my list, is the fact that all of the major cities of the 7K have strong neighbors capable of sacking each other. I believe that most if not all the major cities have been sacked at least once. Please feel free to enlighten me on that front. I can't remember White Harbor or Gulltown ever falling, but I could be wrong.

[Dorian Martell's son]

1: they say all that because they are the last city of their kingdom that was over run by the dothraki. They ain't sheet. 
2: This. Canals, civilian armed forces and bridges over canals. This city would be very hard to take
3: Volantis, The city is more than the old black walls. it could fall easily if there was a slave revolt. Anyone behind the black walls can get starved out
4: Again, the last city of a kingdom. Every other town/city was defeated. This can fall as well
5: Asshai. No point in conquering. no kids, no food, no water. Just show up with a crop of food and barrels of water and you will sail away with more gold and gems than you would know what to do with. Illyrio is one of the wealthiest men in Essos. He regularly trades with Asshai.  There is a reason he can bribe triarchs, cause the golden company to break contract and fund Varys.
 

[Daenerys Targaryen's slave]

Probably the City of Winged Men.

[Lord Vance II]

The secret Valyrian City founded on the southern tip of Sothyros in the aftermath of the Doom. 

But in the realm of reality (that we know of) I'd probably go with Braavos. There is no land approach so any invasion would have to be totally sea based through the teeth of the world strongest navy. 

[Ser Snowflake]

13 hours ago, Dorian Martell's son said:

1: they say all that because they are the last city of their kingdom that was over run by the dothraki. They ain't sheet. 
2: This. Canals, civilian armed forces and bridges over canals. This city would be very hard to take
3: Volantis, The city is more than the old black walls. it could fall easily if there was a slave revolt. Anyone behind the black walls can get starved out
4: Again, the last city of a kingdom. Every other town/city was defeated. This can fall as well
5: Asshai. No point in conquering. no kids, no food, no water. Just show up with a crop of food and barrels of water and you will sail away with more gold and gems than you would know what to do with. Illyrio is one of the wealthiest men in Essos. He regularly trades with Asshai.  There is a reason he can bribe triarchs, cause the golden company to break contract and fund Varys.
 

1. Not true. The Qartheen have fortified cities on the island of Qal. Port Yhos is a large Qartheen town along with Qarkash. The triple walls are one of the 9 wonders of the world and have never fallen. The only powers who had the technology to conquer the city are extinct (Valyria and Sarnor). The slavers of Slaver's bay can't even take Meereen back from the dragon queen. Lol

2. No comment.

3. You may be right in that the city is vulnerable to a slave revolt. I think the Braavosi could probably take the city if it came down to it...if they stirred up the slave population. All it takes is one person to open up the gates to the city.

4. I do wonder why the Jogos Nhai haven't conquered this city yet.

5. You may have a point there. Asshai wouldn't be reaaly worth conquering. But if someone was to try, it would be a race to see who would starve first....the besieged or the besieging army. Any force attempting to conquer the Asshai would need to have an excellent supply line because they couldn't live off of the land. Who knows what the warlocks in the shadow city could cook up during a siege? I do hope that at least one character from ASOIAF make it there by the end of the series.

[Dorian Martell's son]

1: They are the last of the kingdom. That means all others have fallen.  Walls are well and good but as we have seen at winterfell, distracted or otherwise occupied defenders can make it so a few people with climbing gear can wreak havok. Ain't Sheet.
2: so we are in agreement 
3: slave revolts are bad news pure and simple 
4: plot mostly. The author has to write something along those lines 
5: Big city, very few people. No food or water produced but magic and money abound. No reason to conquer. Just trade 

[The Hammer of Justice]

I'd go with Braavos. It can't be invaded by land, the only way is by sea through a narrow passage with the Titan guarding it

 

[Lord Corlys Velaryon]

@The Pimp that was Promised

1). The triple walls (& gates) of Qarth certainly are formidable, but the inner is only 50ft high & I'm not sure if the 30ft outer & 40ft middle are actually garrisoned. Ultimately, Qarth's defense mainly comes down to as you say, its naval superiority. Particularly a united Qartheen front (the various merchant powers pitching in too with their own warships/galleys), they'd destroy any other naval power between say Asshai & the Basilisk Isles attacking them. And also as point out, any others more distant would lose too much strength on the way there (the Braavosi might be able to beat them on neutral ground, but the Iron Fleet - even with the other ~400 Ironborn longships - would be rekt, save perhaps some Euron-esque magical intervention). Though on Qarth itself, even if a fleet was able to surprise the Qartheen in landing an army outside the city itself, they'd still have to destroy the enemy navies to be able to maintain a supply chain for their forces in the inhospitable Red Waste (absolutely the prime land defense). Meanwhile, the Qartheen camelry can attack in raids from the city itself. Really, if you could actually get that far to landing an army near the city, you might as well just go for the harbour direct, tbh.

2). Yeah, nobody's attacked it direct since the Century of Blood (the Sarnori? Targaryens? Other Free Cities?) for good reason. The Titan itself is a remarkable defense feature that would probably stop most enemy ships trying to pass under it & the galleys of the Arsenal would clean up the rest. Even the other (smaller) channels are fortified & patrolled.

3). Agree with Dorian here. Whilst the Black Walls themselves are extremely formidable, they are only (a small) part of the whole city (that is very easily conquerable in comparison). There would be a fair likelihood of a successful slave revolt inside after long enough of a siege (though admittedly, that'd have its own myriad of problems maintaining). They are a naval superpower, but not united enough, with some strength solely on the Rhoyne (for hundreds of miles) & of course far too dependent on slave crews & fighters.

4). It wouldn't be an easy one sure, but unless your a jhattar of the Jogos Nhai, what's the point? And even then, you'd almost certainly be looking south instead. Samyriana, Kakakayanaya, & Bayasabhad would be more fitting here, imo, as any one of them is actually worth taking by any number of potential belligerents.

5). Best left alone. As to Jorah, it's at least partially likely a leftover of when GRRM actually intended for Dany to perhaps go there. Idk, mayhaps he thought Dany would get the best price for eggs there &/or to take her further away from anybody else who could have influence over her (i.e. groom/creep on her for himself).

Of the cities we know enough about, I'd have to go with Braavos. The sister-cities of the Bone Mountains & Qarth up there too.

By the time of the Andal invasion in the Vale, King Yorwyck VI Royce had basically forced King Osgood III Shett (heh) & his men back inside Gulltown itself. Given the extremely close proximity of Runestone to Gulltown, & that the Royces & the Shetts were the Blackwood-Brackens of the pre-Andal Vale; it's not hard to imagine that Gulltown (or Runestone) fell at least once before this time. However, the first confirmation of Gulltown being taken historically is when Osgood makes alliance with Andals under Gerold Grafton to defeat Yorwyck, only to be double-crossed by Gerold:

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King Osgood won his victory, as it happened, but he himself did not survive the battle, and afterward it was whispered amongst the Gulltowners and other First Men that it was Ser Gerold himself who struck him down. Upon his return to the town, the Andal warlord claimed his good-father's crown for his own, dispossessing the younger Shett and confining him to his bedchamber until such time as he had gotten Ser Gerold's daughter with child (after which the father vanishes from the pages of history).

When Gulltown rose against him, King Gerold put down the protests brutally, and soon the gutters of the town ran red with the blood of the First Men...and women and children as well. The dead were thrown in the bay to feed the crabs. (TWoIaF, The Vale)

It then briefly fell to the First Men ~2 generations later:

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Gulltown was retaken by storm when (High King Robar II Royce) sent his own sister inside the walls to persuade the Shetts to rise against the Graftons and open the city gates. (TWoIaF, The Vale)

Northerners threatened it some centuries later during the War Across the Water, but were unable to take it:

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The Arryns sent a fleet up the White Knife to burn the Wolf's Den, and the Starks replied by attacking Gulltown and burning hundreds of ships in their wroth when the city walls proved too strong for them. (TWoIaF, The Vale)

I'm guessing the Royces - long since "Andalised" & presumably loyal vassals of the Arryns (had the War Across the Water started only a couple of generations after Artys Arryn things may have been different) - played a part in this. Perhaps being a threat to the Starks' rear or extra forces manning the walls. Some centuries later, Visenya burns (most of) the Arryn fleet off Gulltown during the Conquest, but doesn't continue the attack to the city itself. (The Targaryen-Velaryon fleet had already been defeated & she'd already proved her political acumen by not burning down Duskendale after they marched with Maidenpool against the newly-landed Targaryen host, instead accepting the surrender of the new Lord Darklyn & commandeering the Dunfort's treasury for the Targaryens' own). And the next time we know that it falls is rather recent:

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Lyn Corbray had slain almost as many men in duels as he had in battle. He had won his spurs during Robert's Rebellion, she knew, fighting first against Lord Jon Arryn at the gates of Gulltown, and later beneath his banners on the Trident, where he had cut down Prince Lewyn of Dorne, a white knight of the Kingsguard. (A Feast for Crows, Alayne I)

(I'd forgotten how so comparatively late in the series this was only first mentioned, though Summerhall, Ashford, & the Bells were only in ASoS).

As for White Harbor, probably not. The Wolf's Den was taken numerous times by various attackers (Sistermen, pirates from the Stepstones, Valemen) over many centuries, but the city itself was only founded sometime after the Manderlys fled the Vale & swore fealty to Winterfell c.700BC. The Worthless War was seemingly ended & the Manderlys have held the Wolf's Den (to some degree, at least, perhaps abandoned at times) & White Harbor ever since, AFAWK.

[The Fresh PtwP]

Braavos, the Arsenal can shit out a war galley in a day. The Iron Bank should be able to pay for an army of sellswords to supplement any standing army Braavos can boast.

Not to mention the Faceless men, an invading force would have to elect a new commander every other day due to assasinations.

[Universal Sword Donor]

I think Braavos would be easier to take than a lot of people give it credit for. A land-based force is in a position to destroy/redirect the aqueduct bringing in fresh water. It can always be taken back but even destroying part of the aqueduct leaves the city in a bad way. The water in the canals is brackish and excess salt intake is pretty bad for the internal organs -- they might have a way to filter it on a large scale but I tend to doubt it. A city that large will have trouble providing the 2+ liters a day people need to survive (cooking, drinking, et al). 

The naval part is the really tricky approach. It might be enough to scuttle ships underneath the Titan, but I can't imagine many sailors would be willing to do sacrifice themselves for it. We also don't know how wide or deep the space is. I can't imagine it's *that* deep but it's definitely narrow enough for the defenders in the Titan to drive ships onto the rocks if they sail in between. If the aqueduct gets destroyed and the lagoon is blocked off, Braavos is not sitting pretty short term. They would clear out the space in short time but the water issue is really going to hit home.

[Lord Corlys Velaryon]

9 hours ago, The Fresh PtwP said:

Not to mention the Faceless men, an invading force would have to elect a new commander every other day due to assasinations.

Mmm, great point.

@Universal Sword Donor I wonder if the aqueduct itself could be used as an invasion entry-point ... Nice point, though. It would certainly weaken the Braavosi resistance for sure. I wouldn't be surprised if the Braavosi have developed some storage capacities from the sweetwater canal, but that would of course only be of limited use in such a situation & most likely only a/v to a certain economic & political class. The normal canal water can be drunk if boiled, but that of course also isn't feasible large scale. I'd have to think that the Braavosi would have the aqueduct well guarded, but who knows.

[Universal Sword Donor]

2 hours ago, Lord Corlys Velaryon said:

Mmm, great point.

@Universal Sword Donor I wonder if the aqueduct itself could be used as an invasion entry-point ... Nice point, though. It would certainly weaken the Braavosi resistance for sure. I wouldn't be surprised if the Braavosi have developed some storage capacities from the sweetwater canal, but that would of course only be of limited use in such a situation & most likely only a/v to a certain economic & political class. The normal canal water can be drunk if boiled, but that of course also isn't feasible large scale. I'd have to think that the Braavosi would have the aqueduct well guarded, but who knows.

Breaking the aqueduct strains the resources on two front:

1) lack of freshwater immediately ready to use

2) puts additional stress on the lack of usable wood nearby because of the boiling

Barges have a shallow draft but surely putting a boom over a canal/river shouldn't be too hard for a hostile force. It worked for the Lannisters at RR.