Quote:
Originally Posted by Guinevere
I only wonder how Legolas could have aquired the skill to build a seaworthy boat and manage to sail and steer it across the Sea! Sailing needs some practice! He had always lived in the woods and to my knowledge never spent any time at the seaside. But someone must have taught him... 
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Well, first consider that he had, by that time, been living in Ithilien for close to 120 years - plenty of time to learn the art from Gondorian shipwrights at Pelargir or Dol-Amroth. Having the sea-longing already awakened in him, he would have been anticipating the time when he would finally "follow the longing in his heart" and sail away -- and would have been looking to develop his learning.
Also, when it says "he built a grey ship in Ithilien", it doesn't need to be interpreted that he built it "single-handed". The learning, then, would be developed in his community. And that could well have been assisted by contact with Mithlond in the North (as well has Gondor) for, while Cirdan had left, nothing reports that ALL of the mariners chose to leave at that time.
Similarly, while it suggests that he took Gimli with him, it never says they were the ONLY two persons on the ship.
So, I suggest he took the 120 years to, among other things, develop a community of mariners (drawing on the ship learning of Gondor and Mithlond), build a sea-worthy ship, and (at the end) captain a ship on which Gimli was a passenger (and companion) but which was sailed by a band of Elves led by Legolas.