I'm turning my party into sailors...

[Burley]

So, it appears I have a passion for putting my players in a situation that I have no idea how to run.
Basically, on Friday, they're going to set sail across a vast ocean, comparable to that of the Pacific, stopping at an island on the way, for character development and possible side quest. Imagine sailing from Japan to the US, stopping in Hawaii.

Well, I'm not a sailor, nor have I ever played one on TV, so I don't know what to do. It's a D&D 3.5 campaign, and I'm using the Dawnforge campaign setting (though, I know most of The Playgrounders aren't familiar with it.)
What I need to know:
What size boat would be suitable for a party of about three dozen, 6 of whom are the PCs (Level 5, but their power level is over 10,000)? The ship used to be a freight vessel, and was used to smuggle supplies to "the resistance."
What kind of encounters could I throw into the trip? I'd like to have a storm or two, definately monster attacks. Maybe there is a mini dungeon in the ship, with traps set by the resistance members to prevent pirates from stealing their cargo/info.
How long would this trip take? The time is fairly relative, but, I need to know, just in case they ask. The boat isn't magical or anything, though, about 90% of the NPC crew have psychic abilities (dubbed psionics in-game, but I'm not statting them).

So, any assistance would be helpful and appreciated. Thanks.

[Hal]

Stormwrack is usually the "go-to" sourcebook on anything naval.

My own advice, from experience, is to be very careful about the timing of events.

Chances are, your players are just hitching a ride with someone rather than commanding the vessel themselves. This can lead to a situation where for the next couple of sessions, your players are just watching as events come at them.

You either need to set up an atmosphere where interpersonal RP will drive the trip, or script your encounters well. Too contrived, and the players might get bored. Too loosely defined, and they might not know what on earth to do with themselves.

[Ascension]

Only one stop between Japan and the US? Hmm... That's a mighty long trip for a sailing vessel. You can manage it, but you're going to need a lot of salt beef, hard tack, and fresh water in the hold, and finding a spring on the island in between will be crucial.

Oh, wait, what am I thinking... this is D&D... and you probably have a cleric. Okay, you can get away with carrying fewer supplies if you can Create Food and Drink.

Are you crossing the equator during the journey? If so, you're likely to hit your campaign setting's version of the doldrums. They're not just annoying, they can be lethal if your supplies run out before you get a good wind. Magic will really come in handy here.

As for the ship... you'll either want a carrack for cargo capacity and stability in rough seas or a caravel for speed and maneuverability... which your smuggler friends would find handy for their primary occupation. You can manage either with a crew of three dozen, though a crew of that size might be a bit small for a carrack and a bit large for a caravel.

A carrack would probably weather storms a good bit better than a caravel, although both are fully capable of making it through... and fully capable of sinking en route. I hope your smugglers are good sailors.

Monster attacks at sea aren't a bad idea. D&D has a lot of fun critters you can use for that. The number one thing you need to remember about fights at sea... particularly fights this far from land... is that any battle against something that's more maneuverable in the water than your ship is a defensive action, and if your boat sinks, you're all dead. If a hole gets put in the hull below the water line... you may very well die. If you lose enough masts and/or sails to prevent you from making sufficient speed... you may very well die... slowly. If a creature of sufficient size attacks without warning from underneath the ship... you may die before you even realize you're in an encounter. You're going to have to be very careful in designing these encounters if you want to keep from TPKing your party.

Alright now... Columbus's journey was roughly 4000 miles, give or take a hundred or two, and it's 5142 miles (straight line) from San Francisco to Tokyo. This seems rather fast, but Wiki says that Columbus's little trip lasted from the August 3rd to October 12th. I'd say, then, that your voyage will take somewhere between two and three quarters and three and a quarter months, depending on conditions.

If we assume that the ship has primarily been used for coastal smuggling in the past and that monster attacks are fairly uncommon, then its arms will probably be quite light. Depending on your tech level they could have... hmm... maybe six to twelve small cannons or... probably just crossbows for the crew if you don't have cannons yet.

If you're attacked by pirates they'll be in smaller, more maneuverable, more heavily armed vessels, and they'd probably tear you apart if you didn't have PCs on board. You're certainly not likely to see them on the open sea, but the closer you are to shore the closer you are to their hunting grounds. If you tick of the wrong person and end up attacked by, say, a galleon... run away. And if running doesn't work, hope your wizard prepared a lot of fireballs.

The on-ship dungeon isn't a really good idea. No matter how valuable their cargo, rigging traps on board a ship is too risky. Besides, why would the PCs want to be getting where their smuggler friends don't want them to be going? Trying to skim a little off the top, are we?

Has any contact been made with "Hawaii" or "Japan" before by any people from "the US"? Is there any sort of trade relationship between them? If your crew is making first contact, it'll be interesting, to say the least. If there's hostile relations between the countries you could end up with the "Japanese" navy being sicced on you. If there's a formal trade relationship and your vessel isn't properly licensed for trade with "Japan," then you could end up in trouble with the "US."

And that's about all that comes to mind right now.

[Burley]

Okay. I'll give some more info...if you insist.
They are starting at the freshly ruined port city of Landsgate. It is the only "civilized" city on the continent of Tamerland. The rest of the area is dense jungle, inhabited by dinosaurs, lizardfolk, and the occasional doppleganger, who head there to be worshipped by the lizardfolk (they do that...I dunno.)
The stopping point is a small nation known as The Dreaming Isles. It is inhabited 99% by a sub-race of humans called Salt Bloods. They are sea faring folk, and a lot of their racial abilites have to do with sailing and drinking. They're sailors, through and through. One of the party's "clerics" is a Salt Blood, and is heading home to inform his people that a prominent member of their people, the Mayor of Landsgate, has been killed by the Yuan-ti slavers the party just kicked off the Tamerland.
Landsgate was demolished by the slavers in a massive blast, which admixtured psionics and polymorph magics to turn the inhabitants of the city into disfigured snake creatures. Many of them fled into the forest, but the few that stayed agreed to help man a vessel to get the party home. The afore mentioned Salt Blood "cleric" will end up being the captain, since he's the only one who knows about sailing.

So, the players will have to be in control, otherwise the ship won't go.

[Ascension]

So let me get this straight, you've got one experienced sailor commanding a crew of total novices who also happen to be disfigured snake/man hybrids? Where'd you get the vessel? How heavily provisioned is it? Do the snake-men still have hands and feet? If not, can they still climb rigging? How long do you have to train the apprentice sailors?

And Dawnforge is that pre-god campaign setting where there aren't any real clerics, isn't it? I'm not sure that there'd even be sea-worthy ships in a prehistoric campaign setting.

[Burley]

It's not prehistoric. It's just the time when Gods aren't Gods yet, merely Immortals. They lack the worshippers. There are definately sea vessels. I swear it.
The crew came on boats, and they know enough to follow orders and do common sense stuff. But, none know how to navigate or command the entire ship. The one PC, however, wrote his character around this knowledge.
Most of the NPCs that are manning the vessel are humanoid. Some have tails instead legs, now. Some have grown large teeth. Most have scales, have lost hair. That kinda stuff. They're basically experimental Yuan-ti.
As I said before, the city they started in was a port city. When the slavers came to the continent, they killed off most of the authorities, leaving only the dock master alive. He was locking up ships and the crews who were suspected of trying to stop the slavers were killed. After the party drove off one slaver, his brother came and Ka-boomed the city. It left all the buildings irradiated, and most of the docks. The vessel they took was one of the latest to arrive, and was docked far enough away that it was spared most of it's damage. It's abandoned and, until claimed by somebody else, belongs to the citizens of the ruined city. They offered to take the party home.

[Triaxx]

Columbus was looking for Atlantis, and was working his way southward on that voyage, so that added time to it.

[KillianHawkeye]

Seriously???