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As long as you buy into the idea that a race the size of 4-year-old humans can be dangerous anywhere, I don't see that the sea would be particularly different.
The materials the halflings are using to build ships are the same as those used by larger races, so I don't see any reason that the ships would need to be smaller. For ships of the same size, I'd expect a larger crew with Small creatures, of course.
The other choice would be to give sea-borne halflings some of the same advantages enjoyed by land-bound halflings. If halfling ships/boats are significantly more nimble than those of larger creatures, they could avoid the attacks of larger ships. Also, a halfling ship might have s shallower draft, so halflings could sail in shoaling waters denied to larger ships.
My first thought is to have the halflings use shallow-draft multi-hulled ships or boats like catamarans or trimarans. These could provide both of the advantages noted above. (Note that smaller creatures that aren't as ravenous as Tolkien's hobbits wouldn't need as much hull volume for supplies as larger creatures.)
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Pros:
Higher dex means they're nimble in the rigging.
They have better a.c. wearing light armor.
They have better to hit with missile weapons.
They're small, so they take up less room.
Cons:
They're not too strong, so a lot of the labor on a ship is difficult for them.
Depending on whether they eat like the hobbits in LOTR, you either need less food, or as much food, as for a same-sized crew of humans.
First of all Ya drink Rum not red wine. Second and more to the point think of this with there size and there natural dexterity. emagine all the flitting around the halflings could do. emagine if you will a ship filled with small acrobatic creatures each armed with daggers swords ax's flintlocks etc. A ship like that would not have a crew it would have a swarm of two legged phirrana. now if you combine that with a bit of gnomish enginuity and dwarf craftsminship then you have yourself something to be feared and respected on the high seas.
Halflings would make the best seafarers ever!
The dex thing, the bonus to climb, the bonus to thrown weapons, all are good selling points.
Even the penalty to strength isn't that big a problem, since lots of work on a sailing ship is team work.
But the biggest reason (and also the reason why halflings should rule the world), is that halflings need to eat way less and drink less. If they are sailing in ships with the same capacity as regular ships (and why wouldn't they?) they could stay at sea for way longer or they could carry more cargo. In either case they've got a big advantage over medium sized creatures.
Back in Mystara halflings were dreaded pirates, or at least that's what it said in the five shires gazeteer.
Now, see - I like the "phirrana" image. I think my hang up is a question of scale. I was looking for a reason to explain why a race 3 feet tall would make ships of the same size and scale as those crewed by 6 foot tall humans. I mean, halflings wouldn't build human sized homes (as a general rule), why build human sized ships? But if they have a pack of small vessels....hmmm. I have to think about that.
Actually that still makes a lot of sense. You need a ship big in order to keep it safe and avoid capsizing. Plus all of the obvious advantages mentioned involving a large ship filled with a tiny crew.
Halflings could be interesting mariners. Their small size would enable them to navigate through rigging a bit more effectively than medium creatures. The dex bonus would help. The strength penalty would be SOMEWHAT mitigated by teamwork (although some jobs would still require plenty of strength, although mechanisms could be introduced to help) One advantage that springs to mind is that they would probably build ships that, OVERALL, are similar in size to those of medium races for cargo and equipment holding but the height of the decks could be reduced by half, making the ship comfortable for small creatures but forcing any medium creatures to crouch to navigate around which could be a significant advantage if you're ever boarded by the ingame equivalent of the Royal Navy. As far as the food storage is concerned, the food would still go bad, stale, or rotten at the same rate unless magic is involved, and let's not forget a key problem for all sailors, pirate, merchant and navy alike: scurvy due to a lack of vitamin C, owing to the fact that fruits and vegetables deteriorate relatively fast at sea. Meat at least in the form of fish and marine creatures can be had relatively easily, and fresh water (unless magic is common) will also be an issue. Check out Stormwrack for a look at a goblin crewed ship adventure-The Sable Drake.
In my Halfling Navy campaign, the main ships that form the fleet are actually bigger than human vessels. They are in fact the largest vessels that sail the oceans of my homebrew. This is because of several factors.
The Halflings are from an empire that covers a huge land area and are used to everything being bigger.
The design of the ships is based on medieval chinese junks, some of which were hundreds of feet long.
Magic and some technology help offset the work necessary to run the ships.
They use specially trained Sea Otters to help fish when on the open sea, which are kept in partially flooded bulhead compartments on the biggest ships.
There should, of course, be smaller ships designed for battle. Smaller means they could be harder to hit, they're not nearly as easily boarded, and they're pretty much worthless to any larger race looking to capture vessels.
You should also have ships built on the larger scale of human vessels for cargo and passenger purposes; these ships should have certain areas designed around larger races - the cargo hold, so ports can have people assist them with the loading and unloading, and passenger areas for the obvious reasons. Restricted areas, however, should be built for small sized races to make it more difficult for any hostiles to wreak havoc on the ship.
Also, the mariners themselves should have a keen eye for their size in mind. They should take advantage of swarm/close quarters fighting techniques, taking feats that allow them to share the same square and fight effectively, or increase flanking bonuses... things like that (I know there's more, but my brain fails me at the moment. Others are welcome to add to this train of thought).
The human sized ships, in fact, would have the advantage of the space to support two different crews. One for the maintenance and running of the ship, and a group of elite warriors that defend the ship when the time comes (and also assist with various duties when they're not needed - fighters with some mariner skills).
So, yeah. I think small races could make awesome mariners.
Aquela is a partially developed setting that has a lot of seafaring that you can borrow. If I'm remembering correctly, it had halfling pirates wandering its seas...
First of all Ya drink Rum not red wine. Second and more to the point think of this with there size and there natural dexterity. emagine all the flitting around the halflings could do. emagine if you will a ship filled with small acrobatic creatures each armed with daggers swords ax's flintlocks etc. A ship like that would not have a crew it would have a swarm of two legged phirrana. now if you combine that with a bit of gnomish enginuity and dwarf craftsminship then you have yourself something to be feared and respected on the high seas.Now, see - I like the "phirrana" image. I think my hang up is a question of scale. I was looking for a reason to explain why a race 3 feet tall would make ships of the same size and scale as those crewed by 6 foot tall humans. I mean, halflings wouldn't build human sized homes (as a general rule), why build human sized ships? But if they have a pack of small vessels....hmmm. I have to think about that.
Why would pirates build their OWN ships when there are so many ships out on the seas perfectly sea-worthy enough already.