The sailing in Black Flag Resynced is the best part, right up until a bigger ship folds your starter Jackdaw like paper. The early hours are a difficulty wall dressed up as an ocean. Here's how to get over it without reloading twenty times.
Upgrade the ship before anything else
Pour your first plunder into Hull and Broadside Cannons, in that order. Hull keeps you alive; broadsides do the work. Those two carry you through most early and mid-game fights on their own. Crew Quarters matter for boarding, but they're lower priority since fresh crew is easy to come by. The materials you're hunting are Metal and Wood, so glass every passing ship with your Spyglass and chase the ones riding low with cargo.
Know when to run
Early on, higher-level ships and naval forts will end you in seconds. That isn't a skill issue, it's a maths issue: your hull can't take the hits yet. Scout every target with the Spyglass before you commit, and leave the forts alone entirely until you've unlocked the mortar. Once you have it, open fights by raining mortar fire from range, then close in with broadsides when the target's already hurting.
Two officers to grab
You can recruit specialist officers who each bring a naval perk. Two are worth going out of your way for early. Padre's Ram Dash turns your bow into a battering ram for big collision damage. Lucy Baldwin's Perfect Brace is effectively a parry for the ship: time it right and you shrug off an incoming volley entirely. Learn that timing and the hardest early fights stop being a coin flip.
Do all that and the Caribbean opens up fast. Ignore it and you'll spend your first evening at the bottom of it.
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