I stayed a week there in my aunt's super dope house. Best time this summer. Make sure to hit up murock's fudge and get some penuche fudge. best stuff ever. south beach in by far my favorite beach with the best waves but its not that great for skimboarding but i still had a great time. Also, small island + gentle slopeing roads + low traffic = great longboarding.
Make sure to take a drive through the bluffs both during sunset and after dark. amazing views. during a thunderstorm was cool too but it was really sketchey since your car is basically the highest point.
you're gonna see alot of stuff about the black dog shops. dont waste your time on their way overpriced hipster crap. Theres also a seafood place in the northwest part of the island in edgartown that looks like a pub with a bar inside but its a seafood place, whatever you do, dont go in. the food was overpriced, the portions were terrible, and the food sucked. and i asked for a rootbeer and they carded me. i was like ROOT BEER. she said I D. i loled and got a sprite.
and i think it was like marthas or something, it was the best icecream shop ive ever been in. go there.