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Some of the more experienced guys have been very helpful to me so let me take a shot at helping you out. As far a spots for shore fishing, I can really only speak to the Vineyard on the south cape. If you do decide to look there try south beach. There is an access road through Katama and you can drive a 4 wheel drive vehicle all the way close to Chappy without any permit. You can also try Gay Head which is the west end of the island. The tough part about Gay Head is that you must park and walk a mile or 2 to get to the best spots. Perhaps some of the other guys that fish near Sandwich can help you with closer locations.
Terminal gear would depend on the type of bait you are fishing. If fishing at night I recommend live eels. You can buy the eel hooks that are tied with a 60 lb leader and barrel swivel all together. They come in packs of 2 for about $2-$3. Use a fish finder above the barrel swivel with a good size pyramid weight depending on the tide/current. 16 oz is probably about average for what I use.
Good luck.
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