The Western Isles
A number of island kingdoms lie off the Sword Coast. Most prominent among these is the Moonshae Archipelago. Riven by war between the native ffolk and the northlanders, neither side has yet gained a decisive advantage. Although the invasion of the northlanders has been temporarily stalled, the ffolk were too exhausted by the fight to capitalize on the advantage and it appears as though both sides will simply regroup, likely for the span of a generation, before resuming the war again. There are three notable exceptions to this general state of affairs. The island of Snowdown labors under the brutal occupation of Amn, who have repeatedly put down revolts and stripped the island of most of its resources, Oman's Isle has been occupied by fomorian giants, and Moray is overrun by lycanthropes of the People of the Black Blood.
The other island of major note off the Sword Coast (besides Orlumbor, in Waterdeep's sphere of influence) is Mintarn. Ruled over by the ancient red dragon Hoondarrh who demands regular tribute from the inhabitants, Mintarn had a brief period of prosperity when Lord Neverember used them to replace his navy, shattered after a failed war with the northlanders. The influx of gold led Hoondarrh to demand more tribute, the economy collapsed due to lack of currency, and the shipbuilding industry folded. Nothing makes a dragon stupid like the promise of gold.
Orlumbor is firmly in Waterdeep's sphere of influence, but for the sake of convenience will be mentioned here instead. It is an island of shipwrights and the key to Waterdeep's worldclass navy.
There are other islands in the region, but none of them came out of the Spellplague very well except the Nelanther Isles, and those did well because they're full of pirates of every race and description imaginable. Lintan blew up and then phased into an alternate world ruled by dragons for a century, and while they've recently returned, they're very much worse for wear. Nimbral was so reclusive in the first place that people barely noticed when it was transported to Abeir for the duration of the Spellplague.
The important islands here are firstly the Moonshaes, because they're potentially valuable naval bases that can be used to strike against or interdict trade to almost anywhere on the Sword Coast, including the Lands of Intrigue, which means anyone who controls both the Moonshae Isles and a powerful enough navy to resist anyone who wants to take them has control over the entire Sword Coast, full stop.
This brings us to the second important group of islands, Orlumbor and Mintarn, both of which have a demonstrable capability to produce a navy worthy of Waterdeep, the greatest naval power on the Sword Coast (not including the Lands of Intrigue, as Calimshan does have a comparable and perhaps even superior navy). Controlling only one of these islands means that a rival may control the other, so the best thing to do would be to control both of them. If you are not Waterdeep, this is going to be difficult. Even if you are Waterdeep, you still have to kill an ancient red dragon in order to secure the loyalty and longterm economic viability of Mintarn.
If you are not Waterdeep, you must additionally find some way to secure the loyalty of Orlumbor, which is firmly in the Waterdeep sphere of influence since their entire economy is building ships for the Waterdeep Navy. Any effort to take control of the island (even non-violently) would be tantamount to a declaration of war on Waterdeep itself.
As for the Moonshaes, the obvious route to power is to draw out some concessions for naval bases from either the northlanders or the ffolk in exchange for resolving the current stalemate in their favor. The northlanders have a powerful navy of their own and thus it would be wise to side against them simply because defeating them means one less competitor navy on the Sword Coast. That said, defeating the northlanders in a naval/amphibious war for an island chain is no mean feat, so particularly if your party needs immediate control of the Moonshae Islands in order to project naval force against another enemy (perhaps Baldur's Gate or Neverwitner or especially Waterdeep, in which case having the powerful northlander navy on your side is the only thing that will make you competitive against the Sword Coast's naval superpower), siding with the northlanders may be a defensible choice.
Either way, Oman's Isle, Moray, and Snowdown are largely inconsequential. Oman's Isle would not be especially difficult for a veteran adventurer party to reclaim, nor would assisting the ffolk in their resistance against Amn's tyranny (although in the latter case it is important to do so subtly, as a war with mighty Amn would be unwise for almost any sphere of influence on the Sword Coast), and this would help to solidify control over the region. After all, any island you don't control is a potential naval base for an enemy. Moray might be harder, depending on just how much a taste you have for hunting down lycanthropes, but its position on the western end of the archipelago means that the only navy that can reach it without being interdicted by your fleet is one based in Evermeet or Maztica. Neither is especially likely to be a major concern, but if you have a taste for hunting the hunters, it can't hurt to be thorough.
The Nelanther Isles could be a target, but if you don't mind quite a bit of pillaging in enemy territory, they could also be used as a mercenary army. Some pirates might resist having even one nation's shipping taken off the potential list of targets, but dealing with them will only prove your might to the others. If you already have a powerful navy, you can flush out the pirates from the Nelanther Isles fairly easily. Pirates never fare well against organized navies, as they are both disorganized, having no unified command above the rank of captain (and occasionally commodores of small fleets) and poorly disciplined, abandoning ship whenever the tide of battle is against them. Pirates are in it for the cash, not king and country. Even so, the pirates of the Nelanther Isles are not likely to be a high priority target. While victory is virtually guaranteed, whatever navy fights the war against them will be entangled for several years and weakened for a decade or more afterwards. With the northlanders on one side and Calimshan on the other, even Waterdeep would be foolish to weaken themselves like this (especially after it's only just recovered from their losses to the northlander navy under the rulership of Lord Neverember).
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