Re: Fishers Island
West harbor has good holding just east of the channel, before you get to the inner harbor. Anything northerly will get rocky, but prevailing winds are protected. You can dinghy in to the Fisher's Island Yacht club and walk to the Pequot. Had a tremendous scallop special this past summer. You may see some of the wealthiest people on the planet, who belong to the club on the private East end, along with locals who just got off work and everyone in between. There is no where else to go. I have a lot of memories in there.
My family spent a lot of time on Fisher's Island when I was a kid. In fact, we just had a reunion there this past summer. It was our most common summer vacation spot as we knew many out there. The locals don't really want tourism, they vote down hotels, B&Bs, etc, all the time. However, if you're polite and friendly, they are welcoming. Approach it this way. You are on horseback in the wild west and come upon a remote town and would like to board your horse and get some rest. Come across like you are entitled to your vacation on Martha's Vineyard, as long as you pay, and they wont' even let you in. That's not what they are there for. Approach it like a polite and friendly stranger asking for permission to stay a short while and you will be welcomed and fed.
When I was a kid, the police would literally stand on the dock at each arriving ferry and interrogate people that arrived. Are you visiting someone? Do you have a place to stay? If they didn't like your answer, they would put you back on the ferry. That doesn't happen anymore, but it's their history.
If you can make it work, and anyone can, it is one of the most beautiful, peaceful places on earth. The upside to rejecting high volume tourism is noticeable and that's why they do it.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.