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I have gone a few times (last year) and several this year. Most of the time it was mid-day fishing along the soft side east beach or a few spots around jamestown. I have not landed a huge fish yet but is is fun to paddle out to a school of feeding bluefish that are well beyond casting range.
There is no doubt in my mind that this could be an outstanding platform to hover in the perfect zone with eels. You can get to the place where it is difficult to cast to or for that matter even walk to, yet to dangerous for a power boat. I plan to take my new fishing kayak over to cuttyhunk this fall (mid-late sept) and cherry pick some nice nights/early mornings in decent weather/surf condions to troll my eels around. If the conditions don't permeit I will not even put it in the water. But gererally speaking on an island you can find someplace to fish. Boating a 50 could be an "issue" but I will worry about that when the time comes. :-)
In general, I do tend to take too much stuff when I fish. (When I go to BI for a week my explorer is jammed packed!) But kayaking has displined me to trim the load. (and secure everything to the boat)
I am slowing working my way into the sport.
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