My sailing skills are at:
Left Broadside (1/5) - I mainly concentrate on the Right Broadsides.
Right Broadside (5/5)
Full Sail (4/5)
Come About (1/5)
Open Fire (0/5)
Ramming Speed (1/5)
Take Cover (1/5)

Windcatcher (5/5)
Tacking (0/5)
Treasure Sense (5/5)
Taskmaster (0/5)

Leadership (*/*)

2 points left that I cannot make up my mind to put into task master or just left broadsides.

Left Brodside (5/5)
Right Brodside (4/5) <- was gonna put one more on it but ran out of points
Full Sail (1/5)
Come About (1/5)
Open Fire (3/5) <- usefull when brining down masts
Ramming Speed (1/5)
Take Cover (2/5) <- oops
Leadership (i just have it i dont know how to give it more points)

Windcatcher (2/5) <- oops again
Taking (1/5)
Treasure Sense (4/5) <- was gonna max this out too
Taskmaster (3/5) usefull when solo

Left Brodside (3/5)
Right Brodside (3/5)
Full Sail (2/5)
Come About (1/5)
Open Fire (1/5)
Ramming Speed (1/5)
Take Cover (1/5)
Leadership

Windcatcher (2/5)
Taking (1/5)
Treasure Sense (5/5)
Taskmaster (5/5)

This is what I'm aiming for, it leaves me with 1 point I think i'm going to put on take cover, I do wish I had not put more than one point in wind catcher and full sail.

With the addition of Leadership, I'll say that this'll have to be it now:

5/5 Left Broadside
5/5 Right Broadside
1/5 Full Sail
1/5 Come About
1/5 Open Fire (Considerable for more)
1/5 Ramming Speed
1/5 Take Cover

5/5 Windcatcher
1/5 Tacking
0/5 Treasure Sense
5/5 Taskmaster

26/26 total + Leadership

Just an update:

Since the Weapons Update - and the Boss Battle 'upgrade' - I'm almost thinking about Take Cover again. The serious upgrade to the Bridge Cannons are causing real headaches (my first pirate - no problem on those bridges before the upgrade - now - I haven't made a sucessful run once... its shameful...)

The only way I see around it is Take Cover - but with the Boss Battle the only reason to use it - I cringe thinking I may actually have to spend a point on it *grrr* just to get through the battle... never to be used again *grrr*

I'll keep ya posted as to if I had to spend a point on it (I still haven't) or if I'll just try to get in with a crew with someone sailing with the option already...

Ive got 2 points on my big pirate and one on my lil one. It does help but it also can be used on other places too...not just the boss.

Left Broadside 5/5
Right Broadside 5/5
Full sail 2/5
Windcatcher 5/5
Treasuresense 5/5
Take Cover 2/5
Taskmaster 2/5

How can you not take max treasuresense? honestly.

I have none on Treasure Sense, save the stock two (I put two in every skill) for the test pirate. I'm all about ship PvP when it comes, and me guild will two, soon as it gains enough members to actually hold up a War Galleon or War Frigate. (1 and counting!) As well, it may just be, aside from Taskmaster, that the only useful skills in PvP for the ship captain will be battle commands. Thus, I may even consider dropping points from Tacking and Windcatcher.

Then again, this is all for Artful. League is now aiming to be impermeale in private combat, though he now be a longtime member of Gadflies.

Left Broadside (5/5)
Right Broadside (5/5)
Full Sail (1/5)
Come About (0/5)
Open Fire (0/5)
Ramming Speed (1/5) (Good for a extra speed boost)
Take Cover (1/5)
Windcatcher (5/5)
Tacking (0/5)
Treasure Sense (5/5)
Taskmaster: (3/5)
Total (26/26)
My dream build.