Im making a 2D, topdown pirate adventure game set in the 17th century carribean. You can have up to 5 ships, but you only control your flagship. Enemy has max 5 ships as well in each fight.

My idea for boarding ships is like this:

- You must soften up the ship with guns first, they will slow down and you can get alongside them to start boarding.
- When boarding the "ship fight" continues at the same time. This means other ships may fire on you while your crew is boarding their friend. They may also fire on any other ships you have in your groups (and your ai-controlled support ships does as well).
- After winning the boarding the enemy ship can be plundered (takes a little time so you may skip it) and you may then resume to "ship fight" remaining enemy ships or board them as well.
- Defeated ships that you do not board may sink after a while and then you loose the potential loot of that ship
- If you loose a boarding (or loose when the enemy boards YOU) its game over (same as If your flagship is sunk by guns.

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Does that seem reasonable / fun?

Now for the actual fighting (crew vs crew) im thinking just have the numbers of men tickle down each other until one side wins. Crew quality may be a factor, and some sort of morale factor. But I dont have any idea how to make the actual fighting more active for the player. Any ideas?

Here is a screenie to give you an sense of the perspective/scale:

If you are only allowed to control one ship of yours it will be extremely frustrating, as you have to watch your AI-controlled ships do stupid things like steering badly and taking unnecessary hits.

When there is a boarding battle the opposing crews are mixed and firing on these ships would hit both, so it might be wise to avoid doing that, event though it might be possible to do (also for AI).

I dont think they would have started plundering while the battle is still continuing. It might be useful to just take over that ship temporarily and only collect/transfer loot when everyones safe after the battle.

Ships dont sink by themselfes unless there is a leak in their hull. They might be taken back or shot on until they have one though.

Why would it be game over when you still have those other ships in your fleet? That could get very frustrating.

May I suggest, if you have not already done this, that you spend some time researching in detail how this sort of thing happened in reality?

Well I agree on your points, but how would you handle it in a game to avoid frustration?
Or to put it like this: is there any games that actually handles multi-ship boarding?

(my old version of this game was set in ww2 times, there was no boarding. When all ships were defeated using guns, you could loot some cargo from the defeated ships. Not very realistic but it worked. In the 17th century it seems strange to not have actual boarding).

1) Maybe a boarded ship gets "fully defeated", meaning it stays passive for the remainder of the battle. When the battle is over (ALL enemies are fully defeated or sunk), loot can be taken?

2 ) Boarding (fighting crew vs crew) may be on another timeline, so when it starts (between two ships) it gets fully resolved before ships continue to fight (ship fighting is "frozen"). This may feel strange however. Maybe other ships simply do not shoot at ships already engaged in boarding combat. They await "their turn", ready to resume fighting you once you have finished boarding one ship.

3) If you loose your flagship you (the player avatar) are dead. If you loose a supporting ship you can continue playing and replace or repair that ship.