You're getting the right info here. If you are limited on time, but really want to get to MV, I agree that you sail direct to Menemsha from Newport, come right up Vineyard Sound. You can anchor
or get a mooring in the bight, but as mentioned it can be exposed and uncomfortable depending on weather - but if it is only a night and you don't mind some rocking, get a mooring there. Anchor
, if you are not leaving the boat for long, but it sounds like you want to look around. You can get one of a handful of moorings inside, but they may be taken. There is transient slip space, but limited. Anyway, get on a mooring, dinghy
in and since you are "broke", skip the cab and jump on the best bus system ever and go where you wish to go, VH, OB, South Beach, Edgartown, then bus back to Menemsha, get a seafood quesadilla (really) at Menemsha Seafood and go out and sleep (maybe), then check your Eldridge and head back to Newport out of Vineyard sound.
But, if you don't mind possibly missing MV and you want to see Cuttyhunk as a stop over or possible final destination, come toward Buzzard's Bay. As noted above, although there is current in BB, it is no where near as important as the flow in Vineyard Sound, so don't go nuts worrying about BB current. If leaving Cuttyhunk for VH, focus on getting slack or current with you through Quick's, but most importantly focus on getting northerly current toward VH after exiting the hole. Make sure you are getting enough time to ride that freight train to get up to VH, or you'll have a long, long day if it turns on you. Eldridge, Eldridge, look at the graphical flow charts
and then work them back to the time tables. If you end your trip at Cuttyhunk, just head on back to Newport, ideally with the flow. I agree any of these alternatives better than mooring in RI and taking ferry, but don't know what you're looking for. Have fun.