This route is spectacular! The best of the island in the winter, very few people encountered, 45 degrees, sky and water were the same color. I'd scoped most of this route in advance, which was helpful. Strong ankles and trail shoes are also helpful, the terrain is super rough. Planning around the lowest tides of the month was important, as was planning for stream crossings (although these streams are always moving around)!
Started at Menemsha about two hours before the lowest tide was predicted. Got the rockiest miles out of the way when my legs felt spritely, then had many glorious sandy beach stretches to bound about between slower rockier sections. Got to know the properties of beaches made up of every size of rock possible, from marbles to boulders. Each type has pros and cons for running on, all are difficult.
This was an unsupported attempt. I carried about 1 liter of water and a few snacks. I was dropped off at Menemsha parking lot, and picked up near the Tashmoo jetty.