Re: Newport/Martha's Vineyard/Nantucket--your feedbacked needed!
Newport bridge is going to $5 each way, it is a long haul from there and cabs are generally very expensive in Newport anyway.
Make your way over to Wickford, get a mooring and then its a very short cab ride. With any luck, you can give someone at one the several marinas some gas money to take you over.
The Fast Ferry ride is about 90 mins to Vineyard Haven.
Another plan, which I would suggest, is to sail to Menemsha, the western most part of the Vineyard. It should only be 5ish hours, which is probably the amount of time you will goof around with cabs, arriving early for the ferry, returning, etc. There isn't much action in Menemsha, but you can now take a cab wherever you like on the Vineyard. If you can't get inside the cove, you'll just want to be sure you only go when winds are S-SW (which is prevailing). Excellent holding, if you don't find a mooring.
If you get tempted to sail on to Vineyard Haven, you really want to time the current Vineyard sound, which can be as high as 3-4 knots on the nose, if you do it wrong.
From there, you can head to Block Island and begin your LIS voyage.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.