We currently have a discrepency in the timeline regarding Charles Widmore.
On the one hand, from "Dead is Dead" we know that he wasn't exiled until after the purge (1992), because he was exiled on the submarine. The sub belonged to the Dharma Initiative and I doubt they would have just lent it out to the Others. In addition, regardless of the submarine, we know that it was at least after 188, because Danielle Rousseau and Alex were on the island during his leadership.
On the other hand, we have Miles' comment from "Because You Left" that it took Widmore "like 20 years to find this place the first time". Even allowing for the "like" in Miles' comment, I feel it is safe to say that it took him more than 12 years to find the island.
So, how would he have been looking for the island for "like 20 years" when he was on the island only 12 years ago. I think the answer lies in Ben's comments to Widmore at his exile. Ben says "You left the Island regularly. You had a daughter with an outsider."
How did Widmore leave the island regularly? Well, not by submarine. As mentioned above, it belonged to Dharma until the purge and Penny, presumably the "daughter with an outsider," is more than 12 years old. Also not by donkey wheel, because he was able to return to the island (leaving "regularly" implies returning regularly as well). It is possible, I suppose, that he left by boat, but that seems awkward, especially given the last option, which is the unexplained method that the Others use.
In "Cabin Fever", we saw that Richard left the island at least twice to visit Locke as a child. No submarine or donkey wheel, so he used some other means. In "Meet Kevin Johnson", Michael asks Tom "So you people can just... come and go?" and Tom replies "Some of us." Given the time constraints on Michael's off-island time, this suggests that Tom is also using a fairly instant means of transport to and from the island. Whatever else these scenes tell us, they do serve to show us that the Others have some unknown means of coming and going from the island. And this must have been the means that Charles Widmore was using to leave the island "regularly."
We don't know much else about this means of transportation. Specifically, we don't know if it gives the person using it any idea of where the island is. Given the island's and the Others' habit of secrecy, it seems unlikely. More likely, it allows the user to go where the want off island and then return to the island.
So, Charles Widmore was coming and going from the island, but that doesn't mean he knew where it was.
If we loved the "outsider" with whom he had Penny, he might well have wanted to bring her and Penny to live with him on the island. Alternately, he likely knew he might eventually be exiled. He is many things, but stupid isn't one of them. He broke the rules and knew it.
Regardless of the reason, it seems safe to assume at this point that Charles Widmore was already trying to locate the island even as he was able to come and go from it. Theory by jrrl
On the one hand, from "Dead is Dead" we know that he wasn't exiled until after the purge (1992), because he was exiled on the submarine. The sub belonged to the Dharma Initiative and I doubt they would have just lent it out to the Others. In addition, regardless of the submarine, we know that it was at least after 188, because Danielle Rousseau and Alex were on the island during his leadership.
On the other hand, we have Miles' comment from "Because You Left" that it took Widmore "like 20 years to find this place the first time". Even allowing for the "like" in Miles' comment, I feel it is safe to say that it took him more than 12 years to find the island.
So, how would he have been looking for the island for "like 20 years" when he was on the island only 12 years ago. I think the answer lies in Ben's comments to Widmore at his exile. Ben says "You left the Island regularly. You had a daughter with an outsider."
How did Widmore leave the island regularly? Well, not by submarine. As mentioned above, it belonged to Dharma until the purge and Penny, presumably the "daughter with an outsider," is more than 12 years old. Also not by donkey wheel, because he was able to return to the island (leaving "regularly" implies returning regularly as well). It is possible, I suppose, that he left by boat, but that seems awkward, especially given the last option, which is the unexplained method that the Others use.
In "Cabin Fever", we saw that Richard left the island at least twice to visit Locke as a child. No submarine or donkey wheel, so he used some other means. In "Meet Kevin Johnson", Michael asks Tom "So you people can just... come and go?" and Tom replies "Some of us." Given the time constraints on Michael's off-island time, this suggests that Tom is also using a fairly instant means of transport to and from the island. Whatever else these scenes tell us, they do serve to show us that the Others have some unknown means of coming and going from the island. And this must have been the means that Charles Widmore was using to leave the island "regularly."
We don't know much else about this means of transportation. Specifically, we don't know if it gives the person using it any idea of where the island is. Given the island's and the Others' habit of secrecy, it seems unlikely. More likely, it allows the user to go where the want off island and then return to the island.
So, Charles Widmore was coming and going from the island, but that doesn't mean he knew where it was.
If we loved the "outsider" with whom he had Penny, he might well have wanted to bring her and Penny to live with him on the island. Alternately, he likely knew he might eventually be exiled. He is many things, but stupid isn't one of them. He broke the rules and knew it.
Regardless of the reason, it seems safe to assume at this point that Charles Widmore was already trying to locate the island even as he was able to come and go from it. Theory by jrrl