I'm running a game set in the Caribbean and so far my players have been just doing jobs in the local islands. However after basically conscripting a pirate captain and his ship, my players are speaking of gaining a fleet of ships. Heading them off at the pass, I'm considering how to involve this in my games.

That being said, does anybody have any tricks, tips, or ideas of how to involve fleet action in fun, effective, and engaging manner?

The only time there has been sea work we always went under and blast charged the boat/sub/floating door.

Expect to handwave a lot of stuff. Shadowrun rules are written for a small team, and break down very quickly at larger scales (not that this issue is unique to Shadowrun, mind you). So yeah, if your players want to be the new Pirate Lords, have them gather up their pieces-of-eight (or pieces-of-whatever-they-happen-to-have-in-their-pockets, as the case may be), and handwave the shit out of it.

We had a thread about pirate campaigns a few weeks back, dig it up, there's a lot of stuff in there.

I read that thread when it was hot and its about that group of players having a boat and doing pirate shenanigans. My players aren't looking to become pirates, just Shadowrunners with a bunch of boats.

Is there a difference?

I would say yes. Pirates loot and pillage indiscriminately whereas Shadowrunners are commissioned for a certain job. That is the key difference.

My players aren't going to abandon terrestrial gameplay and focus of looting and smuggling; that would waste their talents. They are merely entertained with the prospect of owning their own fleet. The boats won't be the central tenet of their play style, merely a weapon in their arsenal.

Ahh. So when you say "fleet" you are referring to the maritime equivalent of a garage full of cars: they will own multiple watercraft, but will only use one at a time, rather than hiring crews for each and deploying them as a single operational unit?

I say they should start funding pirates. Become shareholders or Admirals. Anything you can get on a run that they could use, ship it to your pirates. Keep them the most well armed and inspire loyalty. Slowly it could be like a minor version of Trust Fund or less restrictive version of Day Job.

Fleet Action is naval engagement between groups of ships larger than a squadron.

Before I could super serious input I'd need to know more about the group-but in general:

• What makes the sea so dangerous, obviously, is that it's unpredictable. Weather should play a role in this sort of game. if they're not investing in some good equipment to track the weather, I'd let it bite them in the ass here and there. Obviously you don't want to bog the whole game down on just weather-but a friendly reminder that Terra Firma this isn't.
• Speaking of the ground beneath their feet remind them that the Sea is huge. Finding anything while out to sea can be a chore. which of course brings up the resource management part of the game: Food and water can't just be bought at the local Stuffer Shack. You need a port or a friendly vessel. Fuel is a commodity. Again not something you want to bog the game down with but here and there a game where they need to worry about beans and bullets isn't a bad thing.
• Shark Week! In all seriousness, the wild life can be a concern-admittedly a tasty one at times.
• Pirates-both the real kind, and the kind in uniform. A stop by a national power's Navy can be a heart breaker!
• Port-making port is good. If you speak the language, and know how to not look like a victim to the locals. or like a bunch of dirty scum bag criminals to the assorted Law Enforcement officials out there. Language barriers can be reduced by Linguasoft's-but not necessarily eliminated.
• Magic: The Bermuda Triangle, assorted spirits, Voodoo-I mean let's face there's literally hundreds of years of sea stories told by old salts out there. The players could pretty easily get in the middle of this.
• Outer Space: Personally I'll never run a team into outer space-but there are launch platforms in this area. Which means business is there!
• Aquacology anyone? Sure there's bound to be some everyone knows and avoids-but there's bound be some out there people don't readily know about.
• Submarines and SeaPlanes. Nothing can ruin your day faster, right?
• Island Prisons!

That's just a list I put together while watching a TV show. I'm sure you can get more!

If the odds are amazingly against you then hire up low grade runners who will surely die in the massive naval fight and use their failed attempts to cover up whatever your team is doing.

Cyberpirates was one of my favorite world books for SR3 (although the Caribbean chapter did lean to the silly), and an island-hopping style campaign is a neat idea, I think. It does seem like it'd be hard to hide though, particularly against satellites. I think I'd want a submarine if I could get one.

Vehicle combat has always been a troublesome aspect to the SR rules; it tends to be boggy and complicated and still pretty vague. I've always tried to strip it down to a few rolls to cover the immediate action and handwave the rest.

It would seem like in a Carib League based game, it would all be boats and aircraft. You'd probably want land vehicles on the larger islands and those trips to the mainland, so you could get a ship large enough to transport a few cars that would be nice. You'd probably also want to register your boats under different names with the different countries, so if your registration is challenged in the CL you could still dock in the CAS or Azzie ports.

Boats (and vehicles in general) are neat, but vehicles with spirits and spells backing them up are awesome. Even a weak spirit's Movement power is a pretty significant boost to a vehicle's speed. Put a powerful spirit on it and you can water ski behind a rowboat (although if you have a cybermonster rowing, you may be able to do that anyway).

The thing I like about the occasional run on a cruise ship or oil rig is unlike mainland runs, if things go sideways you can't just walk away (although you may cling to the levitating mage, which has happened a time or two in my group). If a vehicle gets damaged, it's not just about stopping it's also about sinking. It's everything that can wrong on a typical run plus everything that can go wrong on the sea.

Aha. So the boats will be the core element of the game. Let's be honest, here, even a modest "fleet" (a dozen or so fishing trawlers or equivalent) requires enormous amounts of time, effort, and money put into upkeep. If your runners have even the vaguest ambition toward fielding anything that even remotely resembles a paramilitary naval force, the game is going to be all about that force: where they're going to get it, how they're going to equip it, what they're going to use it for, and who they're going to hire it out to. Accept that fact now, and everybody's life gets easier. Also, I return to my original recommendation: handwave the everloving fuck out of the whole affair, because any attempt at realism will turn the game into BookkeepingRun.