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Martha's Vineyard has an excellent bus service.
We have stayed in Vineyard Haven and taken the bus to Edgartown, Oak Bluffs etc.

Martha's Vineyard Transit Authority

Plus Edgartown has become a lot more tricky now that the ocean has breached the barrier beach at Katama. The currents can be very strong within the harbor.

Wide Breach at Katama Sends Tidal Surge Through Edgartown - 7/4/08 - Vineyard Gazette Online

 

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As others have mentioned your original plan seemed a bit much. Sailing out of NGBay I've been going to all the places you mentioned alternating them every few years for the last 12 or so during our 2 separate weeks of vacation every summer. My only real "advise" to you would be - Fuel Up !! Before my Nauticat I had a couple Catalinas that were decent sailers but of all those years I only actually got to stricly "sail" a couple times to those various destinations. The winds in this area are just not steady or predictable enough to plan a multi-hop "sailing" vacation in a limited time frame. I always ended up Motor Sailing so...... I bought a Motor Sailor. There were other reasons also, but I do my "sailing" weekends on the bay, for vacation destinations it's Motor Sailing 90 + percent of the time

Good point about the fuel.
Also, places like Cuttyhunk have very limited fuel dock hours.
Even in peak summer, it is only open something like 10AM -3PM.

 

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I have a plow, but keep a Danforth as a backup.

 

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Nika:

I believe that we had chatted earlier when you were looking for a marina. You are at Spicers? I am next door at NSY. I have an extra dink if you would like to borrow it for the trip. I am planning on bringing it to the marina in a few weeks. It is a 8 foot Sumner sailing dink with oars. I can't decide if I want to sell it or not. It is fun to have around the mooring field. Don't think that it is right for you long term, but for the trip it is better than nothing.

If interested, PM me. It would be great to meet you as well. You can often find me at the little bakery in Noank on the way to the marina. Julie bakes the best muffins!!!

Mike

I love that little bakery. I always pick up a paper at Carsons and then have my coffee outside the bakery.